
Apartment holiday rentals in Downtown Chicago
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Top-rated apartment rentals in Downtown Chicago
Guests agree: These apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago apartment rentals
Weekly apartment rentals

Kasa | Family 3BD with Gym Access | South Loop

Downtown Penthouse Lake Views #1|Gym, Parking+Pool

Modern Lakefront Oasis with Breathtaking Views!

Loop Loft-Subway & Art Institute

52nd Floor MagMile Penthouse VIEWS Fireplace Pool

Modern Design 3 Bedroom Dandelion Apartment

Sonder Onterie | King Studio Apartment

Chicago Luxury Long Term 30+
Private apartment rentals

Sunny Penthouse - Oakwood Beach

Chic retreat near the best of Lakeview & Wrigley

Luxury Loop Loft

Old Town Tranquility (+parking)

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Humboldt Park Retreat: Skylights & Queen Beds

FREE PARKING Large 2BR2BA by Millenium Park

Bright & Modern 2BR: Perfect City Escape
Apartment rentals with a hot tub

Luxe Ranch & Spa, Euro Opulence, a 4-Season Oasis

The Areal Oasis

Spacious Beautiful Condo

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

Skyline Oasis: City & Lake Views

Penthouse Near Fulton: Skyline, Spacious

Summer Getaway in Prime Location | Pet Friendly

Belmont Pleasures - hot tub / arcade gaming room
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
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- South Bend Holiday rentals
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- Holland Holiday rentals
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- Rentals with an EV charger Downtown Chicago
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Garfield Park Conservatory
- Washington Park Zoo
- Wicker Park
- Illinois Beach State Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
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