Condo vacation rentals in South Loop

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Top-rated condo rentals in South Loop

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Guest favorite
The living room features a spacious, light-colored sectional sofa adorned with orange and black cushions. A coffee table sits in front, accompanied by a cozy pouf on a patterned rug. A mounted TV is visible, along with large windows allowing natural light to brighten the room.
Condo in West Town
4.9 out of 5 average rating, 102 reviews

Welcome to the Chi! Close to Downtown

Welcome to this contemporary, urban retreat in the bustling heart of River West. This entire unit is thoughtfully designed with modern convenience, catering to those seeking stylish and comfortable accommodation. This trendy unit is in a prime location, just a short walk to the Blue Line and minutes away from 90/94. With an array of restaurants, grocery markets, coffee shops, and stores within walking distance, you'll have the best of Chicago at your doorstep. 5 minute drive to United Center.

Top guest favorite
Condo in Wicker Park
4.92 out of 5 average rating, 142 reviews

WONDERFUL WICKER PARK 2BD/2BA w/ patios +parking

Escape into this spacious condo in a bustling top-notch, Chicago neighborhood! 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! - 2 private walk-out patios! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out patio - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Top guest favorite
A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.
Condo in Wicker Park
4.97 out of 5 average rating, 138 reviews

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Superhost
A modern living area is presented with a dark gray sofa adorned with neutral pillows and a cozy throw. A round mirror reflects light, while a white coffee table with a decorative plant sits centered on a plush area rug, enhancing the room's inviting atmosphere.
Condo in East Pilsen
4.8 out of 5 average rating, 197 reviews

Charming Condo near U.C./Loop/McCormick Place

Our spacious 3-bedroom, 2-bathroom condo is designed for comfort and convenience. Perfect for extended stays, it features a dedicated workspace with a desk and office chair, plus an in-unit washer and dryer. Two bedrooms offer cozy queen beds, while the third has a comfortable futon. The master bath is large enough for multiple people to get ready at once, and the fully stocked kitchen is ready for your culinary creations. Enjoy extra privacy in your secluded space within the building.

Superhost
Condo in Chinatown
4.85 out of 5 average rating, 135 reviews

1 #12 - 2 Bedroom 1 Bath Condo - McCormick Place

Beautiful, newly renovated condo located in the heart of Chicago Chinatown with 2 bedroom, 1 bath, a spacious living room and a well appointed kitchen. This premium condo has 4 beds and can accommodate 7+ guests. Minutes to Downtown, McCormick Place, and popular attractions. Walking distance to public transit, stores, Walgreens, Starbucks, and many great restaurants. We have properties here and in the vicinity that can accommodate groups of 27 or more guests. Contact us for details.

Top guest favorite
A spacious living area displays hardwood floors and elevated ceilings. A large flat-screen TV is mounted above a decorative brick fireplace. Natural light filters through multiple windows, illuminating the contemporary furniture arrangement that includes a soft sectional sofa and accent chair.
Condo in Lincoln Park
4.99 out of 5 average rating, 186 reviews

1,800ft² Parking Workspace W/D Full Kitch

• 1,800ft² | 167m² . My home is on the top floor of a four flat Itallian Brick Building . You have 3 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport Note: The fireplace is non working

Guest favorite
A modern living area features a dark sofa adorned with colorful throw pillows. A wooden coffee table rests in front, and light streams in through large windows that offer views of the surrounding city. A dining table with chairs is visible in the background.
Condo in Grant Park
4.89 out of 5 average rating, 160 reviews

Downtown Park #11 - Mich Ave PH | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve 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 bed -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 are looking for a special place, you've found it!

Guest favorite
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Condo in Avondale
4.96 out of 5 average rating, 143 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Top guest favorite
Condo in Grant Park
4.82 out of 5 average rating, 211 reviews

Downtown Lake VIEWS, Mich Ave, Museums 2bd/2ba

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Beautiful views of the Park & Lake ✅ Central Location ✅ Parking garage attached to building ($15-30 / night - Operated by LAZ) ✅ FAST WIFI ✅ Comfy KING beds ✅ Rooftop Deck ✅ 1 block from Red, Orange, Green "L" subway ✅ Close proximity to Park, Soldier Field, Museums

Superhost
The living room features a wall-mounted television above a wooden console, surrounded by decor and framed photos. Comfortable seating includes gray armchairs and a sectional sofa, offering a relaxed setting. Natural light brightens the space through nearby windows, enhancing the airy atmosphere.
Condo in River West
4.82 out of 5 average rating, 242 reviews

Chicago River West 4 Bedroom / 3 Bathroom

Two-level River West home great for travelers who want to see the best of Chicago (its neighborhoods!). The living room is a converted store front, so you benefit from airy ceilings and tons of natural light, which carries into the kitchen - between that and the new appliances, cooking here is a blast. The 4 bedrooms and 3 bathrooms are spread out over both floors, so it's ideal for families and groups of friends - book today!

Superhost
A modern studio apartment features a spacious bed with white pillows and a navy blue blanket. A sleek kitchen with stainless steel appliances and wooden cabinetry is visible in the background. A black sofa and a round white dining table complete the living area, with natural light coming through a window.
Condo in River West
4.74 out of 5 average rating, 170 reviews

Cabin 104 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

Top guest favorite
An open kitchen and dining area features exposed wooden beams and stylish light fixtures. A modern dining table with black chairs provides seating, while a lounge chair is positioned nearby. Decorative plants and art add warmth to the contemporary space.
Condo in Wicker Park
4.95 out of 5 average rating, 137 reviews

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Popular amenities for South Loop condo rentals

When is the best time to visit South Loop?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,092 GYDG$25,928 GYDG$34,083 GYDG$40,146 GYDG$43,701 GYDG$47,047 GYDG$45,165 GYDG$43,283 GYDG$42,028 GYDG$46,419 GYDG$33,874 GYDG$33,874 GYD
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Quick stats about condo rentals in South Loop

  • Total vacation rentals

    Explore 50 vacation rentals in South Loop

  • Nightly prices starting at

    South Loop vacation rentals start at G$8,364 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,690 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of South Loop vacation rentals include wi-fi access

  • Popular amenities for guests

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

  • 4.8 Average rating

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

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