Vacation rentals in Chicago, United States - page 4

Carefully selected & verified rentals in Chicago, United States
Check-in
06Dec2025Select date
Check-out
07Dec2025Select 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 690
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Perfect Place To Enjoy The City Or Just Relax Chicago
The largest option:
4 adults
1 bedroom
2 beds
MapClose to the center8km
  • Air-conditioned rooms with streaming services
  • Historic building with private entrance
  • Fully equipped kitchen and living room
  • Flat-screen TV
  • Fully equipped kitchen
  • Private entrance
Hotel rooms in a historic setting near downtown attractions
FromUS$ 107 /nightSelect
Aurelien Spacious Apartments In The Heart Of Gold Coast Chicago
MapMagnificent Mile400m
  • Rooftop pool with stunning views
  • Air-conditioned rooms with kitchen
  • 24-hour front desk for convenience
  • Rooftop pool
  • Fitness centre
  • Outdoor fireplace
Hotel with luxurious amenities in a vibrant area
FromUS$ 266 /nightSelect
2Br Comfy And Stylish Apt In West Town - Erie 1R
4 adults
2 bedrooms
1 bed
MapVibrant West Town neighborhood2.9km
  • Stylish interior design offering comfort
  • Equipped kitchen for self-catering
  • Air-conditioned rooms for relaxation
  • Equipped kitchen
  • Air conditioning
  • Flat-screen TV
Comfy hotel with stylish two-bedroom rooms in Chicago
FromUS$ 281 /nightSelect
Amazing Location! - Modern 2Br Apts Right Next To Wrigley Field & Transit
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
Great Chicago Getaway 2 Bedrooms Sleeps 1 To 4
Map9.5 km from City Centre300 m from Elston Park
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Bucktown Private Condo
Map5.5 km from City Centre900 m from Damen (Blue Line)
FromUS$ 276 /nightSelect
Lincoln Park Apartment With Backyard!
MapLincoln Park Neighborhood600m
  • Proximity to Lincoln Park Zoo
  • Outdoor dining area with garden views
  • Children's play area for family fun
  • Outdoor dining
  • Children's area
  • Garden views
Modern hotel with family-friendly outdoor amenities
FromUS$ 174 /nightSelect
City-View Chicago 3-Br Rooftop
Map4.0 km from City Centre800 m from Stanton Park
FromUS$ 279 /nightSelect
Flexhome Wicker Park 3Br Dv2
MapVibrant Wicker Park neighborhood0m
  • On-site spa for relaxation
  • Fully equipped kitchen available
  • Stylish rooms in Wicker Park
  • On-site spa
  • Kitchen facilities
  • Stylish decor
Modern hotel featuring spacious rooms with unique decor
FromUS$ 145 /nightSelect
Fully Furnished Extended Stay Work Or Insurance In Chicago
Map10.3 km from City Centre2.5 km from Tilton Park
FromUS$ 133 /nightSelect
Townhome
Map11.8 km from City Centre2.0 km from Loyola University Chicago
FromUS$ 81 /nightSelect
The Brown House - A Luxurious Uchicago Campus Stay
Map10.8 km from City Centre400 m from Cottage Grove
FromUS$ 388 /nightSelect
Modern And Minimalist Studio Apartment - Bstone 105 And 108 Rep
MapMuseum of Science and Industry1km
  • Fully equipped kitchen available
  • Air conditioning throughout the rooms
  • Pets allowed in the property
  • Air Conditioning
  • Flat-screen TV
  • Kitchen Utensils
Stylish hotel offering minimalist design and amenities
FromUS$ 178 /nightSelect
Spacious 2Br South Loop With Skyline View, Optional Parking And Gym Access Near Mccormick Place And Soldier Field
MapNear McCormick Place300m
  • Skyline views from patio
  • Access to fitness centre
  • Pet-friendly rooms available
  • Fitness Centre
  • Patio View
  • Pet Friendly
Modern hotel offering urban views and essential amenities
FromUS$ 514 /nightSelect
South Loop 3Br Group Comfort Near Downtown, Grant Park, Soldier Field And Mccormick Place
MapSouth Loop neighborhood200m
  • Three bedrooms for family comfort
  • Fully equipped kitchen for meals
  • On-site parking for convenience
  • Private entrance
  • Flat-screen TV
  • Air conditioning
Hotel offering spacious accommodation for group stays
FromUS$ 461 /nightSelect
Spiraled Vibes
MapVibrant neighborhood attractions300m
  • On-site spa for rejuvenating treatments
  • Indoor pool for year-round enjoyment
  • Modern rooms with flat-screen TVs
  • On-site Spa
  • Indoor Pool
  • Flat-screen TV
Hotel offering unique leisure experiences in Chicago
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Cozy North Side Oasis
Map6.8 km from City Centre500 m from Humboldt Community Christian
FromUS$ 331 /nightSelect
Chic & Fully Furnished 2Br Apartment - Roscoe 1
Map10.3 km from City Centre
FromUS$ 68 /nightSelect
Chic Chicago Apartment About 1 Mi To Wrigley Field!
Map9.1 km from City Centre1.0 km from Wrigley Field
FromUS$ 139 /nightSelect
Bootlegger House Sleeps 10-20 Free Tv & Parking
Map7.0 km from City Centre1.5 km from Wrigley Field
FromUS$ 265 /nightSelect

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Check-in
06Dec2025Select date
Check-out
07Dec2025Select date
Rooms and Guests2 Guests, 1 Room