
Holiday rentals in The Loop
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Quick stats about holiday rentals in The Loop

Total holiday rentals
Explore 1,120 holiday rentals in The Loop

Nightly prices starting at
The Loop holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 28,470 verified reviews to help you choose

Family-friendly holiday rentals
380 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 550 rentals that welcome pets

Holiday rentals with a pool
510 properties feature pools

Rentals with dedicated workspaces
720 properties have a dedicated workspace

Wifi availability
1,090 of The Loop holiday rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across The Loop rentals

4.7 Average rating
The Loop stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
The Loop’s top spots include Millennium Park, Shedd Aquarium and Willis Tower
Top-rated holiday rentals in The Loop
Guests agree: these stays are highly rated for location, cleanliness and more.

Upscale High-Rise Apt · Rooftop Pool + Views
Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants Unit Highlights: - Stunning views of the city - Black-out curtains & roller shades - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modern design

Kasa | Studio, Walk to Grant Park | 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.

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.

Spectacular 2BR Penthouse in the Loop | Roof Deck
This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 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 Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed. The building has a pool and an amazing outdoor rooftop terrace with 360 degree views of the skyline and lake. This is the best location in the city!

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.

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!

Division St Designer Home In Heart of Wicker Park
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

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.

Sentral Studio Apt in South Loop Chicago
Feel at home amid the Chicago skyline. Designer details and mid-century style elevate everything you touch. An all-in-one living area gives you plenty of room to live and work. The fully equipped kitchen features marbled quartz countertops and a gas range. Please note that layout, furnishings, and views may vary by unit. A $500 credit card authorization applies at check-in and is released at checkout.

Modern 3BR Apartment Near North Ave Shops
Welcome to your bright and spacious 3-bedroom Chicago retreat. Enjoy an open living area, fully equipped kitchen, and cozy bedrooms designed for both comfort and privacy. Large windows fill the space with natural light, while modern furnishings and soft tones create a calm, welcoming feel - perfect for families, groups, or business travelers seeking room to relax and recharge.

South Loop Studio Hotel (309)
Stay in the center of the action in this one-of-a-kind place! You’ll be within walking distance of Chicago's most iconic landmarks. ⚠️ Please Note: Our elevator is currently undergoing repairs. All guests will need to use the stairs to access the unit. We apologize for the inconvenience and appreciate your understanding as we maintain our unique space!
Popular amenities for The Loop holiday rentals
Other great holiday rentals in The Loop

Close to Navy Pier + Restaurant. Bar. Gym.

Level Chicago - Fulton Market

Club Quarters Hotel Central Loop, Chicago

The Royal Sonesta Chicago Downtown

Modern design with VU Skyward rooftop bar

Warwick Allerton Hotel Chicago

Brilliant 2BR/2BA Loft I SuperHost I Sleep 6

The Swissôtel Chicago
When is the best time to visit The Loop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $191 SGD | $194 SGD | $233 SGD | $256 SGD | $318 SGD | $373 SGD | $372 SGD | $329 SGD | $314 SGD | $289 SGD | $227 SGD | $205 SGD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Destinations to explore
- Loft rentals Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with a fireplace Chicago Loop
- Boutique hotels Chicago Loop
- Rentals with beach access Chicago Loop
- Luxury rentals Chicago Loop
- Serviced apartment rentals Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a washing machine and dryer Chicago Loop
- Rentals with an EV charger Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Rentals with an accessible-height bed Chicago Loop
- Rentals with a cinema Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with a hot tub Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with pools Chicago Loop
- Waterfront rentals Chicago Loop
- Hotel rooms Chicago Loop
- Flat rentals Chicago Loop
- Rentals with a firepit Chicago Loop
- Rentals with breakfast Chicago Loop
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- Shedd Aquarium
- Chicago River Walk
- Humboldt Park
- University of Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Donald E Stephens Convention Center
- Union Park
- Frank Lloyd Wright Home and Studio
- Washington Park Zoo
- Garfield Park Conservatory
- Things to do Chicago Loop
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- Art and culture Chicago
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