Condo vacation rentals in Downtown Chicago

Find and book unique condos on Airbnb

Top-rated condo rentals in Downtown Chicago

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Guest favorite

Condo in Chicago

4.84 out of 5 average rating, 305 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.

Mar 2 – 9

G$29,461 GYD per night

Guest favorite

Condo in Chicago

4.91 out of 5 average rating, 121 reviews

Spacious & Modern Family Friendly North Center Apt

Newly renovated, modern kitchen & bath, solar-powered, comfortable beds. Great location in safe neighborhood, Jewel Grocery store, Trader Joe’s, craft breweries, restaurants, bars, Wrigley Field nearby & brown line train to downtown Loop. Families with children are welcome. Owners with 2 young kids live upstairs, we are available to address guest needs. No smoking anything on property. Parties & excessive noise prohibited, max of 6 people allowed inside at anytime. Quiet hours 11 pm - 8 am.

Feb 5 – 12

G$32,053 GYD per night

Guest favorite

Condo in Chicago

4.93 out of 5 average rating, 187 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or North Shore Evanston Hospital? This AirBnb is perfectly situated. An immaculately clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation - red line "El" trains & bus routes. Apt has a private, queen bedroom with en suite full bathroom, living room with queen sofa bed, TV, dining table and kitchenette. Dogs allowed and Parking available for a fee.

Jan 25 – Feb 1

G$20,349 GYD per night

Superhost

Condo in Chicago

4.9 out of 5 average rating, 168 reviews

2BD/2BA MAG MILE MASTERPIECE (+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 an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

Jul 11 – 18

G$107,028 GYD per night

Guest favorite

Condo in Chicago

4.97 out of 5 average rating, 101 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.

Sep 3 – 10

G$32,325 GYD per night

Superhost

Condo in Chicago

4.95 out of 5 average rating, 131 reviews

Grand Avenue Apt 2/west Loop & Newly Renovated!

Welcome! The Grand Avenue apt #2 is a spacious and Scandinavian design inspired 2 bed/1 bath apartment located in the West Loop neighborhood, one of the premier live/work spaces and top restaurant/bar scene in the city of Chicago. The apartment has been newly renovated with a beautiful dining area and kitchen, newly appointed bedrooms with Casper mattresses and a cozy living room. The apartment includes a private outdoor balcony, a large backyard, in unit washer/dryer and electric fireplace.

G$14,409 GYD per night

Guest favorite

Condo in Little Italy

4.96 out of 5 average rating, 120 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.

Jun 25 – Jul 2

G$59,328 GYD per night

Guest favorite

Condo in Chicago

4.98 out of 5 average rating, 234 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

Mar 18 – 25

G$40,794 GYD per night

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.

Dec 6 – 13

G$71,229 GYD per night

Guest favorite

Condo in Chicago

5.0 out of 5 average rating, 100 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.

Jan 2 – 9

G$87,578 GYD per night

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!

Oct 13 – 20

G$20,498 GYD per night

Guest favorite

Condo in Chicago

4.86 out of 5 average rating, 125 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.

Nov 7 – 14

G$23,152 GYD per night