Condo vacation rentals in The Loop

Find and book unique condos on Airbnb

Top-rated condo rentals in The Loop

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

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Guest favorite
A spacious living area features a large sectional sofa facing a media unit with a TV, accompanied by a coffee table. A dining table with four chairs sits nearby. Floor-to-ceiling windows provide bright natural light and a view of adjacent buildings.
Condo in Gold Coast
4.86 out of 5 average rating, 205 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!

Superhost
A spacious living area features a blue sectional sofa and two round coffee tables. Natural light streams through multiple large windows, illuminating the neutral walls and light wood flooring. A potted plant adds a touch of greenery, complementing the modern design.
Condo in East Pilsen
4.82 out of 5 average rating, 140 reviews

Trendy Stay Thats Close to Loop, UC & McCormick Pl

This chic yet homie 2 bedroom condo fits six guests, comes with two full/double size beds, and a fully equipped kitchen. The bathroom has a smart mirror as you get ready to paint the town red. You’ll have a living room area to put your feet up and relax while you watch TV or catch up on some work. There is an in unit washer and dryer for longer stays, or if you need to do a quick wash. Both are brand new. For those traveling with young children we have a pack and play for your youngster.

Top guest favorite
A spacious rooftop deck features comfortable wooden seating arranged around a circular table. The area is adorned with vibrant flowers and a decorative rug, all set against a sweeping view of the Chicago skyline under a soft blue sky.
Condo in Wicker Park
4.94 out of 5 average rating, 184 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this spacious, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Guest favorite
An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.
Condo in West Town
4.96 out of 5 average rating, 166 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

Top guest favorite
A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.
Condo in East Rogers Park
4.93 out of 5 average rating, 274 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed, TV, dining table, & partial kitchenette. NOTE: No full kitchen.

Superhost
A view overlooking a vibrant urban landscape featuring Wrigley Field in the background. Rooftops, utility units, and modern buildings create an interesting skyline. The image captures the spirit of the neighborhood, with hints of greenery and construction highlighting the area's dynamic atmosphere.
Condo in Wrigleyville
4.82 out of 5 average rating, 368 reviews

Dream Condo steps from Wrigley Field!

The space is a dream for any Chicago Cubs fan! Being mere steps from the ballpark and filled with Cubbies memorabilia ranging from autographed game used equipment to authentic stadium seats from Wrigley Field itself, this place has it all! You are sure to impress clients, mesmerize your family and bask in Cubs nostalgia throughout your entire stay! Smell the hot dogs, feel the buzz and hear the Wrigley Field crowd all from inside your living room this summer!!

Top guest favorite
A spacious living area is filled with natural light from multiple windows. A comfortable sofa, adorned with a decorative pillow, is positioned in the corner. A dining table and chair are visible in the background, with greenery seen through the windows.
Condo in North Side
4.97 out of 5 average rating, 189 reviews

Lincoln Park 2bed/2bath in Historic Neighborhood

Just steps from the lively center of Chicago's Lincoln Park and poised above the quiet, tree-lined streets of the coveted Arlington-Deming neighborhood, this residence on the top floor of a three-story walkup is the perfect for families that want to be close to it all! Lake Michigan, Lincoln Park Zoo, multiple parks, transportation, dining, nightlife, and more. We provide one daily parking permit per night of your stay so you can access free street parking.

Superhost
Condo in Grant Park
4.82 out of 5 average rating, 149 reviews

Cozy Downtown MICH AVE #7 | gym+rooftop

Feel at Home and Unwind when you come to Chicago. Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen beds -1 closed & 1 loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you're interested in booking, see our FAQs below.

Guest favorite
A cozy living area is presented with a daybed adorned with blue linens and colorful throw pillows. Light filters through two windows covered with sheer curtains. A wooden coffee table is positioned in front of a neutral-toned sofa, complemented by a bookshelf displaying various decorative items.
Condo in Old Town Triangle
4.88 out of 5 average rating, 177 reviews

Lincoln Park Hideaway - 5 Min Walk to the Park!

800 sq ft 1 Bed 1 Bath Charming garden-level apartment right in the heart of Lincoln Park. Please note that you will need to walk down a short flight of stairs to access the unit. Close to all the best that Chicago has to offer! Walking distance to restaurants, convenience stores, and public transportation. Anything you could want for a nice trip to Chicago to visit friends and family, work relocation, or just explore our gorgeous city!

Superhost
A modern living area features a large black leather couch accompanied by a sleek armchair. Artistic Chicago-themed decor adorns the walls, including a vibrant sign. Natural light fills the space through window coverings, with a stylish area rug enhancing the warm ambiance.
Condo in Ukrainian Village
4.9 out of 5 average rating, 177 reviews

Modern Chicago Movie Themed Apt

Welcome to Chicago at the Movies! An amazing fully updated apartment in the Ukrainian Village neighborhood. This midcentury modern 3 bedroom home is perfect for groups, couples, and families looking for a perfect Chicago vacation. The property is conveniently located on Grand Avenue just minutes by car, bus or train from Downtown and the Lakefront. We are also just a short 5 Minute ride to the United Center for concerts sports and more!

Top guest favorite
The bright living area features a blue sofa with decorative pillows, a wooden coffee table, and a desk chair facing a small workspace. Natural light enters through multiple windows, showcasing the hardwood flooring and modern decor elements, including a framed cityscape artwork.
Condo in Lake View
4.99 out of 5 average rating, 669 reviews

Urban Comfort in the Heart of Chicago

This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and a newly remodeled en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

Top guest favorite
A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.
Condo in Noble Square
4.97 out of 5 average rating, 855 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Popular amenities for The Loop condo rentals

When is the best time to visit The Loop?

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Avg. price€ 100€ 99€ 129€ 132€ 153€ 174€ 178€ 166€ 138€ 179€ 138€ 131
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Quick stats about condo rentals in The Loop

  • Total vacation rentals

    Explore 50 vacation rentals in The Loop

  • Nightly prices starting at

    The Loop vacation rentals start at € 34 per night before taxes and fees

  • Verified guest reviews

    Over 2,080 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of The Loop vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across The Loop rentals

  • 4.8 Average rating

    The Loop stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    The Loop's top spots, include Millennium Park, Shedd Aquarium, and Willis Tower

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