Vacation rentals in Chicago, United States - page 4

Carefully selected & verified rentals in Chicago, United States
Check-in
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Check-out
17Mar2026Select date
Rooms and Guests2 Guests, 1 Room
Chicago boasts attractions like Millennium Park, Navy Pier, and the Art Institute of Chicago. You can also catch a game at Wrigley Field or enjoy the waterfront at Oak Street Beach. Many options await you, from boutique hotels in the West Loop to hotels with pools and pet-friendly hotels scattered throughout the city. This selection includes the best Marriott Hotels, Wyndham Hotels, and IHG Hotels for fantastic stays. Book early, especially during festivals, and use the Blue Line train to navigate easily.
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61-80 out of 712
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Sleek 1-Bedroom Apt In Chicago - East Park Tower 0610 Rep
Map6.0 mi from City Centre200 yd from Maryknoll Seminary
FromUS$ 226 /nightSelect
Mccormick Place 2Br Stylish Suite With Optional Parking And Gym For Up To 8 Guests Near Soldier Field And Grant Park Chicago
Map1.7 mi from City Centre800 yd from McCormick Place
FromUS$ 160 /nightSelect
The Velvet Jazz Haus
Map3.0 mi from City Centre500 yd from Ukrainian Institute of Art
FromUS$ 336 /nightSelect
The Upscale Getaway Near Downtown
MapUnited Center1.6km
  • Air-conditioned rooms with balconies
  • Fully equipped kitchen with dishwasher
  • Children's playground on site
  • Children's playground
  • Air conditioning
  • Flat-screen TV
Hotel featuring family-friendly amenities and convenient dining options
FromUS$ 734 /nightSelect
Wrigley 2Br, 1Ba With Free Parking
Map5.2 mi from City Centre1200 yd from Wrigley Field
FromUS$ 681 /nightSelect
Luxurious New Remodeled
Map12.5 mi from City Centre300 yd from Chip-IN Tours
FromUS$ 127 /nightSelect
Group-Friendly 2Br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field
Map1.7 mi from City Centre800 yd from McCormick Place
FromUS$ 509 /nightSelect
Jeffjack Heated Pool Penthouse In Chicago'S West Loop
MapDowntown shopping destination300m
  • Rooftop pool for relaxation
  • Hot tub for ultimate comfort
  • 24-hour security for safety
  • Rooftop pool
  • Hot tub
  • Fitness centre
Hotel with distinctive rooftop pool and luxury amenities
FromUS$ 364 /nightSelect
Splendid & Fully Furnished 1Br Apartment - Broadway 204 Rep
MapNear North Avenue Beach2.6km
  • Fully furnished luxury rooms for convenience
  • Located in vibrant Wrigleyville neighborhood
  • Flat-screen TV for entertainment options
  • Flat-screen TV
  • Electric kettle
  • No smoking
Hotel showcasing fully furnished rooms in vibrant surroundings
FromUS$ 158 /nightSelect
Sage Modern Apartments Near Union Park In West Loop
Map1300 yd from City Centre1300 yd from Chicago Union Station
FromUS$ 386 /nightSelect
Chicago Charm
Map8.5 mi from City Centre400 yd from Hoyne Avenue Fields
FromUS$ 254 /nightSelect
Goose Island Central Downtown Prime Location With Access To Patio Chi - 1
Map1.9 mi from City Centre600 yd from Chicago Station (Blue Line)
FromUS$ 431 /nightSelect
Studio Flat In The Heart Of Downtown Chicago
4 adults
1 bedroom
2 beds
MapNear North Side600m
  • Stylish rooms with full kitchen amenities
  • Nearby iconic Chicago attractions
  • Outdoor dining area for relaxation
  • Fully equipped kitchen
  • Outdoor dining
  • Air conditioning
Charming hotel offering urban comfort and convenience
FromUS$ 112 /nightSelect
Bucktown Private Condo
Map3.4 mi from City Centre1000 yd from Damen (Blue Line)
FromUS$ 276 /nightSelect
Modern 2Br Loft With Amazing City Skyline View And Optional Parking For 8 Guests Near Mccormick Place And Soldier Field
4 adults
2 bedrooms
3 beds
MapSouth Loop neighborhood200m
  • Amazing city skyline views from rooms
  • Fitness centre available on-site
  • Optional parking for up to 8 guests
  • Fitness Centre
  • Parking Available
  • 24-Hour Security
Modern loft-style hotel featuring skyline views and fitness amenities
FromUS$ 703 /nightSelect
The Double Play - Modern 2Br Apts Right Next To Wrigley Field & Transit! - Perfect For Cubs Fans
The largest option:
5 adults
2 bedrooms
2 beds
MapNear Wrigley Field100m
  • Ideal for Cubs fans and baseball lovers
  • Fully equipped kitchen for family meals
  • Private entrance for added convenience
  • Air Conditioning
  • Flat-Screen TV
  • 24-Hour Security
Apartment-style hotel near Wrigley Field for fans
FromUS$ 82 /nightSelect
Spacious 5-Br Apt Next To Transit Free Parking
MapUnited Center proximity6.1km
  • Five bedrooms accommodate up to eleven guests
  • Located near public transit options
  • Offers free parking and picnic area
  • Fully Equipped Kitchen
  • Air Conditioning
  • Sun Terrace
Hotel offering family-friendly lodging with modern amenities
FromUS$ 376 /nightSelect
Chic Euro City Getaway- Close To Downtown
Map5.0 mi from City Centre400 yd from 51st
FromUS$ 661 /nightSelect
Chateau De Woodlawn - Peaceful 3 Bedroom Apartment.
MapNearby Museum of Science and Industry4.8km
  • Spacious three-bedroom apartment
  • Private parking available
  • Garden views from rooms
  • Private parking
  • Air conditioning
  • Flat-screen TV
Comfortable apartment hotel near Chicago attractions
FromUS$ 265 /nightSelect
2 Bed Apt W/ Office, Free Parking, Near Wrigley
MapVibrant Wrigleyville neighborhood300m
  • Free parking available on-site
  • Rooms equipped with a fireplace
  • Convenient check-in options offered
  • Air conditioning
  • Flat-screen TV
  • Dishwasher
Modern hotel featuring office space and comfortable rooms
FromUS$ 507 /nightSelect

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Check-in
16Mar2026Select date
Check-out
17Mar2026Select date
Rooms and Guests2 Guests, 1 Room