Holiday rentals in The Loop

Panoramic 2BR Penthouse in the Sky | Roof Deck

[NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Summer/Fall 2026. The 2nd rooftop remains open and available to use, including the pool which typically opens around Memorial Day]. This sunny top floor penthouse is in a perfect location with panoramic lakefront and city views in multiple directions. With over 1,300 square feet of space, 13+ foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of downtown

Fulton House #1 (2bd/ 1ba)

Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced apartment has the business-travel amenities you want: ultra speed wifi, work stations, top tier dining options within steps of the front door, Nespresso coffee, bottled water, washer/dryer. First-come parking next door: $20/nt or $200/mo.

Kasa | 2BD Near McCormick Place | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Walk to it all in Pilsen

This 2 bedroom, 1 bath rehabbed apartment is in Chicago’s vibrant Pilsen neighborhood—rated one the coolest neighborhoods in the WORLD by Forbes! It is a short walk to award-winning restaurants, boutiques and cafes on the 18th Street Corridor and a 5 minute walk to the CTA train that will have you to the Loop in about 10 minutes. It was gut rehabbed in 2017, and it contains an updated kitchen and bathroom, central heat and air conditioning, and a private deck off the kitchen.

1BR South Loop Loft I SuperHost + Top Rated!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Lovely 1-bedroom serviced apartment near Museums!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Mich Ave Downtown Penthouse - Rooftop+Gym

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 -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!

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

1bd w/gym, game room, parking. Sleeps 3

Your family will be close to everything when you stay at this centrally-located place. It’s a bigger space closer to downtown with a screening room, pool, spa, bowling lanes, huge gym and more. Every guest will receive a free bottle of wine for choosing us for their stay or a frozen apple pie treat. Early check in and late checkout available occasionally. You can see the speed as it has been tested through Airbnb.

Level Junior Two Bedroom Suite | Fulton Market

Two bedroom, two bathroom suite featuring a king bed, queen bed, and sofa bed. Maximum occupancy is 4. Enjoy access to over 32,000 sq ft of unrivaled lifestyle amenities, including a seasonal outdoor pool, a relaxing hot tub, and a state-of-the-art fitness center. Take in stunning views of the Chicago skyline from our Cloud Lounge, grill meals at the BBQ stations, and enjoy movie or game nights in the media room.

Loop 2BR w/Lake Views | 10 min to Millennium Park

Stunning 2BR with lake and Millennium Park views in historic downtown building. Sleeps 7 with king bed, queen bed, sofa bed, and air mattress. Features 2 bathrooms, full kitchen, washer/dryer, and high-speed WiFi. Walk to Millennium Park (10min), Riverwalk (5min), Art Institute (8min). Building includes 24-hour concierge, gym, and business center. "L" train just 1 block away.