Chicago vacation rentals
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Top-rated vacation rentals in Chicago
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Guesthouse in Chicago
4.99 out of 5 average rating, 776 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.
Dec 11 – 18
Guest suite in Chicago
5.0 out of 5 average rating, 290 reviewsPrivate Lincoln Square one bed+bath studio apt.
Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336
Apr 1 – 8
Apartment in Uptown
4.97 out of 5 average rating, 260 reviewsCozy loft in Chicago's Uptown
Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; small family on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. New!Andersonville, recently voted the coolest neighborhood in US (Timeout’s survey) is only a 15-minute stroll. The CTA's Red Line/Wilson station is 3 blocks away. Overnight street-parking decals also available for guests.
Aug 20 – 27
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago vacation rentals
Chicago fishing vacation rentals
Apartment in Chicago
4.85 out of 5 average rating, 156 reviewsYour brand new Chicago suite (unit 1F)
Jul 9 – 16
Condo in Chicago
4.94 out of 5 average rating, 181 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Sep 25 – Oct 2
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Dec 17 – 24
Guest suite in Evanston
4.97 out of 5 average rating, 212 reviewsA guest suite centrally located, but so quiet...
Dec 20 – 27
Guest suite in Carol Stream
4.94 out of 5 average rating, 279 reviewsHot Tub, Pool Table, Bar, fishing & Kayak on Lake!
Apr 22 – 29
Apartment in Chicago
4.81 out of 5 average rating, 142 reviewsThe Posh Apt. Mins to Downtown & Hyde Park
Apr 18 – 25
Townhouse in Chicago
4.98 out of 5 average rating, 224 reviewsBeautiful Lincoln Park/ De Paul Complimentary Parking Permit
Mar 19 – 26
Condo in Lake View
4.83 out of 5 average rating, 280 reviewsPrivate studio with free garage parking
Apr 9 – 16
Apartment in Chicago
4.83 out of 5 average rating, 388 reviewsLakeview Charmer -with parking!
Mar 6 – 13
Condo in Chicago
4.99 out of 5 average rating, 554 reviewsUrban Comfort in the Heart of Chicago
Jul 22 – 29
Condo in Chicago
4.98 out of 5 average rating, 193 reviewsNear Lake Michigan & Wrigley Field
Sep 6 – 13
Apartment in Chicago
4.98 out of 5 average rating, 174 reviewsSteps to Mag Mile, 2 BD , fast Wi-Fi, W&D
Apr 29 – May 4
Chicago apartment rentals
Apartment in Chicago
4.96 out of 5 average rating, 315 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Sep 30 – Oct 7
Apartment in Chicago
4.87 out of 5 average rating, 481 reviewsLogan Square Studio
Nov 20 – 27
Apartment in Chicago
4.97 out of 5 average rating, 116 reviewsDesigner Avondale Attic
May 23 – 30
Apartment in Chicago
4.98 out of 5 average rating, 245 reviewsAndersonville Cozy 1 bedroom basement suite
Sep 17 – 24
Apartment in Gold Coast
4.91 out of 5 average rating, 134 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Nov 12 – 19
Apartment in Chicago
4.98 out of 5 average rating, 122 reviewsModern Apt with style & comfort in Pilsen Chicago
May 14 – 21
Apartment in Chicago
4.87 out of 5 average rating, 268 reviews1 Bedroom Apartment In Historic Old Town House
Jan 22 – 29
Apartment in Chicago
4.93 out of 5 average rating, 198 reviewsCharming Edgewater/Andersonville Garden 1 bdrm.
Mar 16 – 23
Apartment in Skokie
4.91 out of 5 average rating, 525 reviewsCozy Garden Unit in Quiet Neighborhood
Feb 18 – 25
Apartment in Humboldt Park
4.98 out of 5 average rating, 102 reviewsHumboldt Park Loft
Sep 4 – 11
Apartment in Chicago
4.96 out of 5 average rating, 253 reviewsLogan Square 2nd Floor Chicago Victorian
Dec 27 – Jan 3
Apartment in Chicago
4.92 out of 5 average rating, 180 reviewsTaj Ma-small at Wrigley
Jan 28 – Feb 4
Chicago homes
Home in Chicago
4.94 out of 5 average rating, 204 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
Feb 25 – Mar 4
Home in Chicago
4.95 out of 5 average rating, 111 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Dec 24 – 31
Home in Chicago
4.97 out of 5 average rating, 316 reviewsCozy garden apartment historic Jackson Bvld.
Dec 20 – 25
Home in Berwyn
4.92 out of 5 average rating, 232 reviewsPrivate apartment with retro vibe
Sep 5 – 12
Home in Chicago
4.98 out of 5 average rating, 202 reviewsWrigleyville Southport Studio
Dec 3 – 10
Home in Chicago
4.95 out of 5 average rating, 309 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
Feb 25 – Mar 4
Home in Chicago
4.86 out of 5 average rating, 214 reviewsThe Avondale Guesthouse
Dec 29 – Jan 5
Home in West Town
4.95 out of 5 average rating, 166 reviewsParadise on the Park
Oct 21 – 28
Home in Portage Park
4.98 out of 5 average rating, 175 reviewsThe Evergreen House
May 10 – 17
Home in Blue Island
4.81 out of 5 average rating, 168 reviewsWarm and comfortable inviting Suburban home !
Jun 19 – 26
Home in Chicago
4.96 out of 5 average rating, 195 reviewsDivision St Designer Home In Heart of Wicker Park
Jul 18 – 25
Home in Forest Park
4.9 out of 5 average rating, 218 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
Jul 25 – Aug 1
Quick stats about vacation rentals in Chicago
Total rentals | 11K properties |
---|---|
Rentals with dedicated workspaces | 6.6K properties have a dedicated workspace |
Rentals with a pool | 1.2K properties have a pool |
Pet-friendly rentals | 3.3K properties allow pets |
Family-friendly rentals | 5K properties are a good fit for families |
Total number of reviews | 476K reviews |
Your guide to Chicago
All About Chicago
Settled along the banks of Lake Michigan, the Windy City of Chicago offers world-class dining, exciting architecture, a top performing arts scene, and plenty of excellent museums. With more than 200 neighborhoods calling this city home, there’s a unique aura found in each.
You’ll find historic mansions and upscale shopping in Gold Coast, Gothic-style university buildings in Hyde Park, cool cocktail bars and quirky shops in hip Logan Square, and incredible comedy clubs in Old Town. Enjoy time outside lounging on the city beaches, catch a baseball game at Wrigley Field, shop along the Magnificent Mile, or sample the celebrated dining scene in this dynamic city, the third-largest metropolis in the United States.
The best time to stay in a vacation rental in Chicago
Chicago’s summers are warm and sunny, which means the rooftops and patios are buzzing, and the days are filled with music and food festivals. This is also when the city's lakeside beaches are at their best, so it’s a popular time for booking Chicago vacation rentals. Fall is chilly but pleasant. Winters are downright cold, and you can expect plenty of snow between the months of December and April, but there’s also plenty of opportunity for ice skating in rinks and snowshoeing and sledding down hills in city parks. There are also wonderful Christmas lights at Navy Pier and throughout the city. Expect relatively cool temperatures and a decent amount of rainfall in spring, and pack your waterproof layers.
Top things to do in Chicago
The Art Institute of Chicago
The Art Institute is one of the best museums in the United States with more than 300,000 permanent artworks and many traveling exhibits. Take shelter from the city’s infamous wind and check out world-famous paintings from French Impressionists and modern American masterpieces. Cafes and restaurants are on-site for coffee breaks and leisurely lunches, and the museum also hosts regular lectures and events.
Willis Tower
The tallest building in the world for almost 25 years, the Willis Tower is a 110-story skyscraper that’s now the second-tallest building in the U.S. For a view that can reach Wisconsin and Michigan on a clear day, visit The Willis Tower observation deck. It’s located on the 103rd floor of the building, and you can even step inside glass observation boxes that extend four feet over the street below.
Millennium Park
Located across from the Art Institute, this city park is one of the most recognizable areas in Chicago thanks to the iconic Cloud Gate sculpture, lovingly known as “The Bean.” Rotating sculpture exhibitions and the naturalistic Lurie Garden make for lovely visits in spring and fall. During the summer months, the park comes alive with outdoor concerts, film screenings, dance performances, and even public yoga classes.
Frequently Asked Questions
How is the weather in Chicago?
Chicago experiences a wide range of weather, from hot summers that can reach 95°F (35°C) to chilly winters that can drop to 20°F (-6°C). The city exhibits four distinct seasons, with beautiful spring blossoms, sunny summers, colorful autumns, and snow-dusted winters, perfect for ice skating in Millennium Park.
What are some of the best things to do in Chicago?
In Chicago, you can explore iconic sights like Navy Pier, Cloud Gate in Millennium Park, and Willis Tower's SkyDeck for breathtaking city views. Cultural enthusiasts can immerse themselves in the Art Institute of Chicago or catch an engaging show at the Second City comedy club.
What is the best time of year to visit Chicago?
Summer, from June to August, is often recommended to visit Chicago. During this season, the city hosts various events, including the Chicago Blues Festival and Taste of Chicago, attracting food and music enthusiasts alike. However, the city is vibrant year-round, with winter activities such as ice skating and holiday markets.
What are the best places to stay in Chicago?
Popular areas to stay in Chicago include the vibrant neighborhoods of River North and Gold Coast for their proximity to dining and shopping. Lincoln Park and Lakeview are also often recommended for their leafy streets, local cafes, and proximity to the lake.
What are the best places to visit in Chicago?
Popular places to visit in Chicago include the culturally rich neighborhoods like Chinatown, Little Italy, and Pilsen. Navy Pier, the Magnificent Mile shopping district, as well as green spaces like Grant Park and Lincoln Park, are also frequently suggested.
What are some hiking trails in Chicago?
While Chicago is an urban city, it still has some scenic hiking trails. The Chicago Lakefront Trail, a 18-mile (29 km) path along Lake Michigan, and the North Branch Trail System in the Forest Preserves of Cook County are popular among outdoor enthusiasts.
What are some family activities to do in Chicago?
Families often enjoy exploring the Shedd Aquarium, the Field Museum of Natural History, and the interactive exhibits at the Chicago Children's Museum. A boat tour along the Chicago River, highlighting the city's architectural marvels, is another frequently suggested activity for families.
What are some of the best day trip ideas in Chicago?
For day trips from Chicago, consider a visit to the Indiana Dunes National Park for some beach fun and hiking, or explore the charming town of Geneva for a relaxed pace with boutique shopping. Rockford, with its Anderson Japanese Gardens and Burpee Museum of Natural History, is also a viable option.
What types of vacation rentals are available in Chicago?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Chicago. From over 1,180 condo rentals, over 6,030 apartment rentals to over 1,850 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Chicago?
Yes! Work meets play with ease at over 6,650 vacation rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.
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