Condo vacation rentals in Downtown Chicago

Find and book unique condos on Airbnb

Top-rated condo rentals in Downtown Chicago

Guests agree: these condos are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Condo in Chicago

4.84 out of 5 average rating, 307 reviews

Peaceful & Airy Modern-Chic Condo in Trendy Pilsen

Brand New Private Modern 2 bd 2bth apt for your stay in Chicago. We are located 2 blocks form the CTA line in the heart of Pilsen, a neighborhood Time Out labeled the 10th coolest in the world. Newly renovated, hardwood tiled floors throughout, chefs kitchen, toiletries, brand new furnishings including 2 queen beds, 1 twin sleeper, fresh linen, smart TV (HBO, Netflix, Hulu) wifi, tons of books,coloring books,board games & puzzles! We truly want you to feel like this is your home away from home.

Guest favorite

Condo in Chicago

4.97 out of 5 average rating, 103 reviews

Stylish 3BR + Free Parking 10-15mins from Downtown

This apartment is located in Historical Humboldt Park, a residential area that is an easy 10-15mins drive to Downtown, Medical District, Wicker Park, West Town, Logan Square, and Ukranian Village. Due to the proximity, we host guests visiting for tourism, fests,concerts, sport events , work conferences, weddings, birthdays, and visiting family. There are grocery stores closeby. There’s street parking and a gated private parking available. Location wise, you are close enough to everything.

Guest favorite

Condo in Gold Coast

4.87 out of 5 average rating, 243 reviews

MAG MILE 2/2 w/ Lake VIEWS! (+Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with floor-to-ceiling windows - Tranquil rooftop overlooking Lake Michigan - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Amazing views of the Lake from kitchen/living room We look forward to hosting you!

Guest favorite

Condo in Little Italy

4.96 out of 5 average rating, 123 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Guest favorite

Condo in Chicago

4.92 out of 5 average rating, 115 reviews

Stunning, Spacious, & Sun-Soaked 1br Uptown Condo

Perfect for any type of traveler, my bright and inviting one bedroom condo in Uptown is a sanctuary stocked with every amenity you could need! There's an organized workspace area if you bring your work with you to Chicago, a gorgeous sunroom with a sofa bed, and a beautiful kitchen stocked with everything you could need to whip up a delicious meal. Steps to the lakefront and Montrose Beach and just a 6-minute walk to the Wilson Red Line, you can't beat this location. Book today! Welcome!

Guest favorite

Condo in Chicago

4.86 out of 5 average rating, 119 reviews

Quiet, Modern, Convenient 2 bedroom condo

PLEASE READ DESCRIPTION PRIOR TO BOOKING* Stay at this quiet, charming, Chicago-themed garden unit suite, sitting in the heart of Chicago's historic Bronzeville neighborhood. This convenient location with 1000 sq feet of space is perfect for young professionals, student, small groups, families, and people traveling with children. Easy access to public transportation, downtown Chicago, the Museum of Science and Industry, the University of Chicago, downtown Hyde Park, and so much more.

Guest favorite

Condo in Chicago

4.92 out of 5 average rating, 248 reviews

Old Town Pied-à-Terre w/Pvt Terrace and Parking

Our bright modern 2 bedroom condo has 13 ft ceilings and an amazing private terrace. It's in the heart of Old Town, right on Wells St - steps outside the door are some of the city's best restaurants, cafes, and bars. Just a 5 minute walk to two world-renowned comedy clubs: Second City and Zanies. The Chicago History Museum, Lincoln Park Zoo, and the lake are a quick walk too. The Sedgwick CTA stop is nearby too! Please note: patio cushions are available May through October.

Guest favorite

Condo in Chicago

5.0 out of 5 average rating, 102 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Superhost

Condo in Chicago

4.87 out of 5 average rating, 108 reviews

Spacious Duplex in Great Location

This below-grade unit has everything you want! Nestled on a quiet tree-lined street public transport is close by and downtown is a quick car ride away. The condo has lots of space and all the amenities you can ask for - plenty of parking, a King sized bed with premium linens, a luxury memory foam mattress, walk-in closet to store all your things, double spa shower, and a coffee bar stocked with top shelf Nespresso coffee. This unit books up quickly, so grab it today!

Superhost

Condo in Chicago

4.86 out of 5 average rating, 127 reviews

McCormick 2B/2Ba for up to 6 guests w Opt Parking

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • City Skyline view • 2 shifts Security officers in the building • 2 Queen size beds + Sofa bed for 2 extra guests • Comfortable stay for up to 6 guests at a time • Access to the Gym • Fast Internet • 4K smart HDTV(Netflix) • Fully equipped & stocked kitchen with Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

Guest favorite

Condo in Chicago

4.87 out of 5 average rating, 126 reviews

3D Tour! Designer Condo near Logan Square

Scan QR code in photos for a 3D Tour! What you’ll love: - Totally renovated garden unit, completed in 2021. Everything new. - Upscale furnishings & decor. - Gourmet, fully equipped kitchen w/ new appliances, coffee maker and spices. - Remote work station w/ super fast Wi-Fi (600mb). - Serta queen mattress in master. - Bunk beds w/ full and twin sized memory foam mattresses. - Heat & A/C.

Guest favorite

Condo in Chicago

4.9 out of 5 average rating, 193 reviews

A Stones Throw from U Chicago South Campus!

This 2 bedroom condo has entirely new EVERYTHING! Located in vintage World's Columbian Exposition era building, it's been newly renovated and updated. You can't get much closer to the University of Chicago campus. This quiet condo is within walking distance of lakefront beaches, golf courses, the Museum of Science and Industry, public transportation, and Jackson Park. No pets allowed.