Skip to content
AIRBNB EXPERIENCES

Unique things to do in Chicago

Book unforgettable activities hosted by locals on Airbnb.

Travel like a local

You could summarize “a couple, two, three” (or a few) things to do in Chicago — eat deep-dish pizza, take an architecture tour, soak up the Chicago River on a boat cruise — but that’s only scratching the surface on the fun activities to try here. Eat your way around the West Loop with local foodies; find the underground donut scene (yes, it’s a thing) in River North; forge jewelry with a real silversmith in Ravenswood, or see homes designed by Frank Lloyld Wright, among other Airbnb Experiences.

Top-rated activities

Sail Chicago's Lakefront on a Yacht
Our sailing experience begins at Monroe Harbor right in downtown Chicago. Guests will enjoy a captained cruise on our sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off and motor out to Lake Michigan where we will set sail to a favorable course. Bring your favorite food and drinks, listen to music, relax, and take in the views of our city’s iconic buildings from the lakefront. The courageous can try their hand at the helm and rigging the sails-Captain Greg is a volunteer sailing instructor for a local non-profit and enjoys sharing his knowledge. On hot days be sure to bring a bathing suit to swim in the lake to cool off. Please feel free to inquire about custom bookings. We have hosted engagements, bachelorette parties, corporate outings and many more memorable events! Things to note: Other Airbnb guests will potentially join your public booking unless you reserve the entire boat privately. There are six open spots on a first book first serve basis. We only wait 15 minutes at the dock for a late guest out of courtesy for timely guests. We only cancel for lightning and will refund everyone. If you tend to get motion/seasick, or have a hangover, take motion medication 30 minutes prior.
Explore Dazzling Architecture Interiors of the Chicago Loop
Take the architecture tour voted #1 by TripAdvisor users! We will be taking a leisurely 2-hour walk exploring some of the most beautiful and often overlooked buildings in downtown Chicago, both outside and inside, and learning about the most important and interesting parts of Chicago's architectural history. Visitors often don't know where to go, or even where they're allowed. This experience takes them inside places they'd never even consider, to show off more than 100 years of architecture as it developed here in the Windy City -- including stunning stained glass, atrium-like spaces, 19th century skyscrapers, and more! Great tour for photographers and travel buffs! Some things to note: Bring a camera -- this is an AWESOME way to practice your architecture photography! Also, dress for the weather, and if it's raining, bring an umbrella. Also, please note that if you provide a non-US phone number as your day-of contact number, we **CANNOT** call you if you're lost or late!
MUST HAVE CHICAGO PHOTOS- OUTDOORS
IF YOU DON´T SEE A TIME FRAME THAT WORKS FOR YOU PLEASE CONTACT ME AND WE CAN ARRANGE THAT We’ll start with a talk in Chicago Cultural Center by the bull and get to know each other. If it’s a small group during the experience, we will walk together around various locations but everybody has their own personal time with me while I photoshoot. Together we’ll discover the places and pictures that YOU NEED TO HAVE from Chicago , from the magical MILLENNIUM PARK, THE BEAN , CHICAGO THEATER AND RIVER WALK while I capture moments of you and/or any friends or your partner to take home. Feel free to tell me your ideas or preferences Other things to note THIS IS A SMALL GROUP EXPERIENCE AND EVERYBODY HAS THEIR OWN TIME (YOU CAN ALSO HAVE PRIVATE PHOTO SHOOTINGS IN CASE THAT YOU NEEED SOMETHING MORE PRIVATE) Please feel free to visit more of my work at www.carlacarrascoocampo.com also on IG at carrascoocampo
Lifestyle City Photo Shoot/Tour
Standing in front of a camera can be quite intimidating. With experience both in front of and behind the lens, I will always do my best to help you capture the best natural travel photos in the city of Chicago. Worried about how you'll look? Don't be! I will always show you the photos before moving forward. During this experience I will not only help you receive beautiful photos but I will also try to teach you insight about modeling and photography. This experience will be ideal for individuals who are looking for a city tour but would also love to capture some scenic travel and portrait images. I love to build positive connections with others, so this is great for someone who wants to be more engaged and collaborative with their guide. I will be using a Sony DSLR to capture your candid and lifestyle moments. This includes both portraits and full body shots. If you would like to learn more about the editing process or a photographer's guides, let me know and I am more than happy to share my knowledge. You will select 3 images for edits & receive all unedited photos (usually 250+). Editing does not include body manipulation, but can be requested for an additional charge. If you do not see a time that works for you on the calendar, please send me a message! I do accept larger parties! This is NOT a private photoshoot unless it is booked as a private session.
Chicago Architecture & Highlights
We begin at the Chicago Theater before heading off into the city. We’ll begin by exploring the Chicago Pedway. This network of tunnels and bridges connects skyscrapers and retail stores, so you’ll see how locals move around the city (especially during those Midwestern winters)! We’ll then make our way past City Hall, where you'll get a chance to enjoy the beauty of the historical architecture while your guide shares about its history. You can’t visit Chicago and not see some incredible public art, so next, we’ll stop at the Picasso Sculpture (yes! A real Picasso!). You’ll hear how this piece came to Chicago and how it was received, as you enjoy an up-close Picasso experience with this unique piece of art. Weather permitting (aka, in the warmer months), we’ll then take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, such as the Wrigley Building and Tribune Tower. Finally, we’ll walk down the world-famous shopping district of Chicago’s Magnificent Mile, making our way to the beautiful lakefront parks along Michigan Avenue. At some point, your guide will serve up a delicious local treat for you to enjoy. We’ll end up in the picturesque Millennium Park, home to the iconic Bean sculpture, where your tour ends. If you would like to book this tour for a private group, please message us directly for more information.

Most popular in Chicago

Gangsters and Ghosts Tours
One of the best ways to really acquaint yourself with the infamous city of Chicago is to do it from the streets, through a guided Chicago Gangster Tour or Ghost Tour, detailing the crimes, deals, and charisma that made the city what it is today. We offer a 2 for 1 deal, hosting historically-based guided tours of Chicago’s gangers AND ghost stories, right from the Chicago Loop Vice District. Other things to note Bring your camera!
Spray 'n' Sip- Street Art & Aerosol Workshop
1. Guests join us at our space Studio W.I.P. and dive into the world of spray paint and urban art. All instruction is done by local artists. Each guest will go home with their very own piece of the mural to remember their night. 2. Upon entering guests can relax and enjoy our ever changing gallery. Feel free to bring a beverage. It's BYOB! Guests will unleash their inner street artist on a 50ft mural! This interactive workshop will turn guests into the artist and be guided along the way. Experimenting with lettering, stencils, aerosol, & cap technique guests will experience something truly unique. 3. Our main objective is to break down stereotypes that often are connected with spray paint. Guests will leave with curiosity and basic skills when applying aerosol to boot.
Bikes, Bites & Brews-Signature Bike Tour
Working up an appetite won’t be a problem on this tour! We’ll be sampling from each of Chicago’s four favorite food groups — pizza, hot dogs, brownies and beer. You’ll learn the history behind the foods that made Chicago famous and also get a taste for some of Chicago’s most popular neighborhoods as we cruise through Streeterville, the Gold Coast, Lakeview, Wrigleyville and Lincoln Park during the day. While our evening tour covers the same foods, we stick to the downtown city attraction scene. Come taste the best of Chicago pizza, snacks, and beer while having a blast on two wheels! All Food and Beverage samples included in ticket price. Day and Evening Tours available. 11:30am Bikes, Bites & Brews Tour: Signature Dishes includes the northside neighborhood route through the Gold Coast mansions, Old Town Historic District, Lincoln Park, Lakeview, Wrigleyville (and Wrigley Field), and the Lakefront. 5:30pm Bikes, Bites & Brews: Signature Dishes Tour includes the downtown city route through the Gold Coast, River North, Chicago Riverwalk, Millennium Park, Buckingham Fountain, and the Lakefront. Both the 11:30am and 5:30pm tours include healthy portions of Deep Dish pizza, Chicago hot dogs, locally crafted beers, and dessert to top things off. We look forward to showing you our beautiful city!
Chicago's Underground Donut Tour
On this tour, you'll join me as we explore the city and food culture through the medium of donuts. You'll learn about the history of Chicago, each donut location, how they fit into the larger food scene, as well as try some amazing donuts. We start from Doughnut Vault where we try some of the best donuts you've had in your life. Next we'll stop by Firecakes donuts to try a few of their seasonal flavors. Followed up with Stans Donuts near Michigan avenue and finally, we end at Do-Rite Donuts where they have both delicious donuts and fried chicken (if you want to get nuts at the end of the tour). We look forward to seeing you soon! Other things to note At this time we cannot accommodate, gluten free or vegan diets. Great for groups, bachelor/ette parties, family reunions and team building exercises.
Chicago in a Day
You’ll fall in love with Chicago and its incredible food scene combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Your local guide will meet you in downtown Chicago, an architecture lover’s paradise and home to iconic attractions like The Bean in Millennium Park. At some point, you’ll get the chance to stroll down bustling Michigan Avenue and see the Chicago Riverwalk, where locals love to relax, recreate, and appreciate Chicago’s unique skyline towering overhead. Your guide may show you another locals-only part of the city, the subterranean network of walkways connecting much of downtown, a perfect escape from any blustery weather. The Chicago Loop is where you’ll start your foodie adventure. We’ll dive right in with a Chicago dog and hear all about this street food staple turned haute cuisine, its deep cultural ties, and just how it relates to the city’s official slogan as you pile on the toppings! Among the other foods we may try are sandwiches with fresh, locally made, seasonal ingredients and of course the most generous piece of pie you’ll cut into, the deep dish pizza. At these generations-run shops, you’ll learn how Chicago evolved and how this impacted its food scene. Room for dessert? Your guide will point you in the right direction to finish off your tour with a sweet treat and plenty more to explore!

Activities near top attractions

Photo of Millennium Park
Millennium Park476 locals recommend
Photo of Navy Pier
Navy Pier307 locals recommend
Photo of Willis Tower
Willis Tower149 locals recommend
Photo of Cloud Gate
Cloud Gate164 locals recommend
Photo of The Art Institute of Chicago
The Art Institute of Chicago434 locals recommend
Photo of Skydeck Chicago
Skydeck Chicago52 locals recommend

Things to do near Grant Park

105 locals recommend

Gangsters and Ghosts Tours
One of the best ways to really acquaint yourself with the infamous city of Chicago is to do it from the streets, through a guided Chicago Gangster Tour or Ghost Tour, detailing the crimes, deals, and charisma that made the city what it is today. We offer a 2 for 1 deal, hosting historically-based guided tours of Chicago’s gangers AND ghost stories, right from the Chicago Loop Vice District. Other things to note Bring your camera!
Sail Chicago's Lakefront on a Yacht
Our sailing experience begins at Monroe Harbor right in downtown Chicago. Guests will enjoy a captained cruise on our sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off and motor out to Lake Michigan where we will set sail to a favorable course. Bring your favorite food and drinks, listen to music, relax, and take in the views of our city’s iconic buildings from the lakefront. The courageous can try their hand at the helm and rigging the sails-Captain Greg is a volunteer sailing instructor for a local non-profit and enjoys sharing his knowledge. On hot days be sure to bring a bathing suit to swim in the lake to cool off. Please feel free to inquire about custom bookings. We have hosted engagements, bachelorette parties, corporate outings and many more memorable events! Things to note: Other Airbnb guests will potentially join your public booking unless you reserve the entire boat privately. There are six open spots on a first book first serve basis. We only wait 15 minutes at the dock for a late guest out of courtesy for timely guests. We only cancel for lightning and will refund everyone. If you tend to get motion/seasick, or have a hangover, take motion medication 30 minutes prior.
Spray 'n' Sip- Street Art & Aerosol Workshop
1. Guests join us at our space Studio W.I.P. and dive into the world of spray paint and urban art. All instruction is done by local artists. Each guest will go home with their very own piece of the mural to remember their night. 2. Upon entering guests can relax and enjoy our ever changing gallery. Feel free to bring a beverage. It's BYOB! Guests will unleash their inner street artist on a 50ft mural! This interactive workshop will turn guests into the artist and be guided along the way. Experimenting with lettering, stencils, aerosol, & cap technique guests will experience something truly unique. 3. Our main objective is to break down stereotypes that often are connected with spray paint. Guests will leave with curiosity and basic skills when applying aerosol to boot.
Bikes, Bites & Brews-Signature Bike Tour
Working up an appetite won’t be a problem on this tour! We’ll be sampling from each of Chicago’s four favorite food groups — pizza, hot dogs, brownies and beer. You’ll learn the history behind the foods that made Chicago famous and also get a taste for some of Chicago’s most popular neighborhoods as we cruise through Streeterville, the Gold Coast, Lakeview, Wrigleyville and Lincoln Park during the day. While our evening tour covers the same foods, we stick to the downtown city attraction scene. Come taste the best of Chicago pizza, snacks, and beer while having a blast on two wheels! All Food and Beverage samples included in ticket price. Day and Evening Tours available. 11:30am Bikes, Bites & Brews Tour: Signature Dishes includes the northside neighborhood route through the Gold Coast mansions, Old Town Historic District, Lincoln Park, Lakeview, Wrigleyville (and Wrigley Field), and the Lakefront. 5:30pm Bikes, Bites & Brews: Signature Dishes Tour includes the downtown city route through the Gold Coast, River North, Chicago Riverwalk, Millennium Park, Buckingham Fountain, and the Lakefront. Both the 11:30am and 5:30pm tours include healthy portions of Deep Dish pizza, Chicago hot dogs, locally crafted beers, and dessert to top things off. We look forward to showing you our beautiful city!
Chicago in a Day
You’ll fall in love with Chicago and its incredible food scene combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Your local guide will meet you in downtown Chicago, an architecture lover’s paradise and home to iconic attractions like The Bean in Millennium Park. At some point, you’ll get the chance to stroll down bustling Michigan Avenue and see the Chicago Riverwalk, where locals love to relax, recreate, and appreciate Chicago’s unique skyline towering overhead. Your guide may show you another locals-only part of the city, the subterranean network of walkways connecting much of downtown, a perfect escape from any blustery weather. The Chicago Loop is where you’ll start your foodie adventure. We’ll dive right in with a Chicago dog and hear all about this street food staple turned haute cuisine, its deep cultural ties, and just how it relates to the city’s official slogan as you pile on the toppings! Among the other foods we may try are sandwiches with fresh, locally made, seasonal ingredients and of course the most generous piece of pie you’ll cut into, the deep dish pizza. At these generations-run shops, you’ll learn how Chicago evolved and how this impacted its food scene. Room for dessert? Your guide will point you in the right direction to finish off your tour with a sweet treat and plenty more to explore!

Things to do near Magnificent Mile

238 locals recommend

Explore Dazzling Architecture Interiors of the Chicago Loop
Take the architecture tour voted #1 by TripAdvisor users! We will be taking a leisurely 2-hour walk exploring some of the most beautiful and often overlooked buildings in downtown Chicago, both outside and inside, and learning about the most important and interesting parts of Chicago's architectural history. Visitors often don't know where to go, or even where they're allowed. This experience takes them inside places they'd never even consider, to show off more than 100 years of architecture as it developed here in the Windy City -- including stunning stained glass, atrium-like spaces, 19th century skyscrapers, and more! Great tour for photographers and travel buffs! Some things to note: Bring a camera -- this is an AWESOME way to practice your architecture photography! Also, dress for the weather, and if it's raining, bring an umbrella. Also, please note that if you provide a non-US phone number as your day-of contact number, we **CANNOT** call you if you're lost or late!
Explore hidden bars in Chicago
Chicago offers a lot of hidden bars for night owls. We will start the night at my favorite hidden gem in West Loop, we will spend about one hour here then head to the next bar which is an 8 minute walk. Some of the bars have secret entrances so be ready for a fun night. The bars have amazing cocktails, beers, non-alcoholic drinks, good music and a good ambiance. There are plenty of secret bars and unfortunately we cannot explore all of them in one night. However, I will share with you the location of other secret bars which you can visit later. Please be advised that drinks or food are NOT included. This is not prohibition level speakeasy tour, this is a chill bar hopping experience. I was not born in the early 1900s and don’t know anything about prohibition so don’t ask. Have a drink and relax. Please note the experience time says it lasts 3 hours but you are welcomed to stay at the bars as long as you like. If your preferred hour is fully booked, don't worry, bar fits a fair amount of people, send me a message. There are still some locations that may ask for your proof of vaccination to access the bars. Please bring it with you. A photo of your vaccination card is fine.
Chicago's Underground Donut Tour
On this tour, you'll join me as we explore the city and food culture through the medium of donuts. You'll learn about the history of Chicago, each donut location, how they fit into the larger food scene, as well as try some amazing donuts. We start from Doughnut Vault where we try some of the best donuts you've had in your life. Next we'll stop by Firecakes donuts to try a few of their seasonal flavors. Followed up with Stans Donuts near Michigan avenue and finally, we end at Do-Rite Donuts where they have both delicious donuts and fried chicken (if you want to get nuts at the end of the tour). We look forward to seeing you soon! Other things to note At this time we cannot accommodate, gluten free or vegan diets. Great for groups, bachelor/ette parties, family reunions and team building exercises.
Fireworks Sailing Cruise on a Yacht
Our sailing experience begins at the Monroe Harbor Public Dock (Google maps). Boarding our 37’ luxury cruising class sailing yacht Dragonfly, a Jeanneau Sun Odyssey, we will cast off and motor out to Lake Michigan where we will set sail to a favorable course. Bring your favorite food and drinks, listen to music, relax, and take in the glittering skyline and the city’s iconic buildings from the lakefront. This tour offers an unbeatable up close and personal view of the Navy Pier Fireworks Show- on display every Wednesday and Saturday evenings Memorial through Labor Day. Do note Airbnb experiences are social, and up to 6 guests from different parties can join our standard cruise, however we welcome inquiries about private or custom outings. If you do not see a time on our calendar that works well for you, please contact us! Other things to note New friends will join your booking unless you reserve the entire boat. We only wait 15 minutes for a late guest out of courtesy for timely guests. We only cancel for lightning and will refund everyone. If you tend to get motion/seasick, or have a hangover, take motion medication 30 minutes prior.
MUST HAVE CHICAGO PHOTOS- OUTDOORS
IF YOU DON´T SEE A TIME FRAME THAT WORKS FOR YOU PLEASE CONTACT ME AND WE CAN ARRANGE THAT We’ll start with a talk in Chicago Cultural Center by the bull and get to know each other. If it’s a small group during the experience, we will walk together around various locations but everybody has their own personal time with me while I photoshoot. Together we’ll discover the places and pictures that YOU NEED TO HAVE from Chicago , from the magical MILLENNIUM PARK, THE BEAN , CHICAGO THEATER AND RIVER WALK while I capture moments of you and/or any friends or your partner to take home. Feel free to tell me your ideas or preferences Other things to note THIS IS A SMALL GROUP EXPERIENCE AND EVERYBODY HAS THEIR OWN TIME (YOU CAN ALSO HAVE PRIVATE PHOTO SHOOTINGS IN CASE THAT YOU NEEED SOMETHING MORE PRIVATE) Please feel free to visit more of my work at www.carlacarrascoocampo.com also on IG at carrascoocampo

Things to do near Logan Square

90 locals recommend

Glassblowing in an artist studio
We will be making a unique one of a kind glass paperweight. This hot glass paperweight is shaped using glass tools. Pull and shape the color patterns in this fun experience. Meet us in our small gallery where you will be taken on a tour of a working glassblowing studio. We make barware and art for hotels in our hotshop. After a quick intro to glassblowing and the techniques used, you will be given one on one instruction while creating your glass paperweight. Feel free to bring your camera, fun photo opportunities are to be had! The experience will end with a question and answer time in our gallery. Please wear cotton clothing and closed toed shoes. Guests must come back 2 days later to pick up their glass piece or arrange to have it shipped (we currently only ship within the United States). **Closed Toed Shoes & Cotton Clothing are required to enter the building** Face masks are optional.
Trickery Chicago Magic Show
Chicago’s most entertaining magic show! Fun, intimate, sometimes outrageous, and always hilarious. Door opens 15 minutes prior to scheduled start time. Venue is BYOB. Cups and bottle openers are available if needed. We do not stock ice but there is a 7-Eleven just down the street (3407 N Halsted). Performance runs approximately 1 hour. This experience is ongoing. Future dates will be continually added. Also available for private appointments by request (Monday-Sunday). For corporate bookings: Great for groups, great for teams, and great for team building! Please note that Airbnb is a third party partner for marketing Trickery’s show. Guests find us through various avenues so there may ultimately be as many as 30 other audience members for any given showtime. Social distancing is not a local requirement or feasible in our space. If uncomfortable being around strangers, this experience may not be for you.
Forge a Silver Ring with a Silversmith
At this time, I am requiring all guests to be fully vaccinated *and boosted* against COVID-19 by the time of their workshop and to provide proof of vaccination. In this workshop, you'll make a sterling silver ring through the silversmithing "fabrication" technique. Learn the basics of texturing metal, forming metal with mandrels and hammers, soldering (yes, you'll play with fire!), and decorative finishing and leave with a beautiful handmade ring that will last a lifetime! This is not just some craft project. You will be working on the same tools that I use myself as a professional silversmith and your ring will be professional quality. It's always a fun evening! You'll be floored by what you can create! Other things to note: You will get plenty of ideas for rings during the class. I also encourage you to look at the photos in this experience as well as guest photos for ideas!
Shop Hidden Thrift Stores
A great thrifting trip is all about the thrill of the hunt! Finding the great scores happens early, so we'll get energized with coffee or a snack at our meet-up point, then take public transit to 3-4 of the best thrifting spots in Chicago and spend ABOUT an hour at each. Each spot is at top of my list when I'm looking for my next favorite item. Not only is thrift shopping great for your wallet, it's sustainable for the environment! This tour is intimate and interactive so get ready to thrift with folks who's tastes and lifestyles are completely different from your own. Making new friends is encouraged! Locals are welcome: this tour ain’t only for tourists! This is not a vintage tour. A successful thrift adventure requires vision to see the unique possibilities in an every day item - the right styling can transform something you'd initially pass up. That's where we come in! We are available to help scour the racks, give advice on how that leather jacket or platform shoes look or happy to let you do your own thing! As your experienced tour guide, I will make sure you go with a new favorite item. *If you are interested specifically in vintage finds, please check out my "Hidden Vintage & Boutique" tour on AirBnB! Other things to note Please reach out to me with questions! If you don’t arrive by CTA, I can help you snag a pass at the station together before we begin the tour.
MOLE from scratch, small o private class
IF YOU DON´T SEE A TIME FRAME THAT WORKS FOR YOU PLEASE CONTACT ME AND WE CAN ARRANGE THAT Vegan and Vegetarian options Mole is a dark sauce that has 20+ ingredients, I´m gonna tell yo the story about this traditional family recipe, and the changes than you can find in the different moles around Mexico. We start with a traditional Agua fresca, and then we gonna make our own mole, and we will enjoyed at the end, with chicken, rice and beans. Other things to note if you have a dietary restrictions please let me know in advance, and we can make it special for you.

All activities near Chicago

Gangsters and Ghosts Tours
One of the best ways to really acquaint yourself with the infamous city of Chicago is to do it from the streets, through a guided Chicago Gangster Tour or Ghost Tour, detailing the crimes, deals, and charisma that made the city what it is today. We offer a 2 for 1 deal, hosting historically-based guided tours of Chicago’s gangers AND ghost stories, right from the Chicago Loop Vice District. Other things to note Bring your camera!
Sail Chicago's Lakefront on a Yacht
Our sailing experience begins at Monroe Harbor right in downtown Chicago. Guests will enjoy a captained cruise on our sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off and motor out to Lake Michigan where we will set sail to a favorable course. Bring your favorite food and drinks, listen to music, relax, and take in the views of our city’s iconic buildings from the lakefront. The courageous can try their hand at the helm and rigging the sails-Captain Greg is a volunteer sailing instructor for a local non-profit and enjoys sharing his knowledge. On hot days be sure to bring a bathing suit to swim in the lake to cool off. Please feel free to inquire about custom bookings. We have hosted engagements, bachelorette parties, corporate outings and many more memorable events! Things to note: Other Airbnb guests will potentially join your public booking unless you reserve the entire boat privately. There are six open spots on a first book first serve basis. We only wait 15 minutes at the dock for a late guest out of courtesy for timely guests. We only cancel for lightning and will refund everyone. If you tend to get motion/seasick, or have a hangover, take motion medication 30 minutes prior.
Spray 'n' Sip- Street Art & Aerosol Workshop
1. Guests join us at our space Studio W.I.P. and dive into the world of spray paint and urban art. All instruction is done by local artists. Each guest will go home with their very own piece of the mural to remember their night. 2. Upon entering guests can relax and enjoy our ever changing gallery. Feel free to bring a beverage. It's BYOB! Guests will unleash their inner street artist on a 50ft mural! This interactive workshop will turn guests into the artist and be guided along the way. Experimenting with lettering, stencils, aerosol, & cap technique guests will experience something truly unique. 3. Our main objective is to break down stereotypes that often are connected with spray paint. Guests will leave with curiosity and basic skills when applying aerosol to boot.
Bikes, Bites & Brews-Signature Bike Tour
Working up an appetite won’t be a problem on this tour! We’ll be sampling from each of Chicago’s four favorite food groups — pizza, hot dogs, brownies and beer. You’ll learn the history behind the foods that made Chicago famous and also get a taste for some of Chicago’s most popular neighborhoods as we cruise through Streeterville, the Gold Coast, Lakeview, Wrigleyville and Lincoln Park during the day. While our evening tour covers the same foods, we stick to the downtown city attraction scene. Come taste the best of Chicago pizza, snacks, and beer while having a blast on two wheels! All Food and Beverage samples included in ticket price. Day and Evening Tours available. 11:30am Bikes, Bites & Brews Tour: Signature Dishes includes the northside neighborhood route through the Gold Coast mansions, Old Town Historic District, Lincoln Park, Lakeview, Wrigleyville (and Wrigley Field), and the Lakefront. 5:30pm Bikes, Bites & Brews: Signature Dishes Tour includes the downtown city route through the Gold Coast, River North, Chicago Riverwalk, Millennium Park, Buckingham Fountain, and the Lakefront. Both the 11:30am and 5:30pm tours include healthy portions of Deep Dish pizza, Chicago hot dogs, locally crafted beers, and dessert to top things off. We look forward to showing you our beautiful city!
Chicago in a Day
You’ll fall in love with Chicago and its incredible food scene combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! Your local guide will meet you in downtown Chicago, an architecture lover’s paradise and home to iconic attractions like The Bean in Millennium Park. At some point, you’ll get the chance to stroll down bustling Michigan Avenue and see the Chicago Riverwalk, where locals love to relax, recreate, and appreciate Chicago’s unique skyline towering overhead. Your guide may show you another locals-only part of the city, the subterranean network of walkways connecting much of downtown, a perfect escape from any blustery weather. The Chicago Loop is where you’ll start your foodie adventure. We’ll dive right in with a Chicago dog and hear all about this street food staple turned haute cuisine, its deep cultural ties, and just how it relates to the city’s official slogan as you pile on the toppings! Among the other foods we may try are sandwiches with fresh, locally made, seasonal ingredients and of course the most generous piece of pie you’ll cut into, the deep dish pizza. At these generations-run shops, you’ll learn how Chicago evolved and how this impacted its food scene. Room for dessert? Your guide will point you in the right direction to finish off your tour with a sweet treat and plenty more to explore!

Your guide to Chicago

Where do locals hang out in Chicago?

Pilsen (Lower West Side)

Chicago has long attracted writers, musicians, artists, and other creatives. Take in the arts, dining, and nightlife of the Pilsen neighborhood to see firsthand where the people who live here go out to enjoy life’s finer things in areas such as the Chicago Arts District, home to National Museum of Mexican Art, the Chicago Art Department, and more.

Hyde Park (South Side)

For a low-key day, head to the South Side neighborhood of Hyde Park where you’ll find people roaming tree-lined boulevards en route to indie bookstores, under-the-radar museums, and the University of Chicago to enjoy prolific Gothic architecture.

Logan Square

Want the Wicker Park hip factor without the brunch wait lines? Check out the Logan Square neighborhood. Here you can get your fix of Michelin-rated restaurants and cocktail bars before cozying up indoors at the Logan Theatre for an indie flick. On Sundays, take a stroll through the farmers’ market that operates all year. For those who want to get hands-on, try making your own street art in a nearby studio with local artists.


What do locals eat in Chicago?

When it comes to what locals eat in Chicago, it can depend on who you ask. No one is going to tell you not to grab a slice of deep-dish pizza or a hot dog, but also that there’s more to savor than these classics. Dry-aged steaks on the Loop, West African cuisine in Bronzeville, tacos in Little Village, pierogies downtown: the food here a reflection of this multicultural Midwestern city.

The Andersonville and Argyle neighborhoods are a must when it comes to food. On Argyle Street, a cluster of Southeast Asian restaurants offer some of the best Asian food in all of the city, meanwhile in Andersonville you’ll find Turkish, Lebanese, and Swedish eats.


What is unique about Chicago’s architecture?

Chicago’s unique architecture is the result of an otherwise tragic historical event: the Great Fire of 1871 which destroyed most of the downtown buildings. By the 1880s, a group of architects called the Chicago School began to promote a new way of building known as “commercial-style” architecture characterized by steel-frame construction and large plates of glass. The result? The world got the first modern skyscraper, the Home Insurance Building, in 1885. Since then, Chicago has always been a world leader in design, with notable styles such as Chicago bungalows, two-flats, grandiose graystones, and Polish cathedrals.

Whether it’s your first visit to Chicago, or you’re a lifelong resident, there are plenty of fun architecture-related activities (both indoors and outdoors) to experience this iconic piece of Chicago history firsthand.