Vacation rentals in Chicago, United States - page 4

Carefully selected & verified rentals in Chicago, United States
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Check-out
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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 621
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Modern 2Br Loft With Amazing City Skyline View And Optional Parking For 8 Guests Near Mccormick Place And Soldier Field Chicago
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
Great Chicago Getaway 2 Bedrooms Sleeps 1 To 4
Map5.9 mi from City Centre400 yd from Elston Park
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Prime Location! - 1Min Walk To Wrigley Field - 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
Bucktown Private Condo
Map3.4 mi from City Centre1000 yd from Damen (Blue Line)
FromUS$ 276 /nightSelect
Irving Park Updated Vintage Top Unit 2-Flat
Map6.7 mi from City Centre1000 yd from Addison Station (Blue Line)
FromUS$ 124 /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
City-View Chicago 3-Br Rooftop
Map2.5 mi from City Centre200 yd from North/Clybourn
FromUS$ 949 /nightSelect
Fully Furnished Extended Stay Work Or Insurance In Chicago
Map6.4 mi from City Centre500 yd from Columbus Park
FromUS$ 133 /nightSelect
Chic & Updated Studio Apt In East Lakeview - Barry S1
2 adults
1 bedroom
1 bed
MapNear Wrigley Field and Lincoln Park1.4km
  • Modern studio with updated amenities
  • Air conditioning for comfortable stays
  • Flat-screen TV for entertainment options
  • Air Conditioning
  • Flat-screen TV
  • Kitchen Utensils
Contemporary hotel near popular attractions in Chicago
FromUS$ 168 /nightSelect
Freshly Minted 2Br - Elegance & Comfort In Central Chicago
Map1.2 mi from City Centre1500 yd from United Center
FromUS$ 708 /nightSelect
Mccormick Place Amazing 2Br Suite With City View And Optional Parking For Up To 8 Guests Near Soldier Field And Lakefront Trail
MapSouth Loop neighborhood0m
  • Views of the Chicago skyline
  • Fully equipped kitchen available
  • Optional parking for convenience
  • Fitness centre
  • City view
  • 24-hour reception
Hotel featuring urban views and family-friendly amenities
FromUS$ 389 /nightSelect
Perfect Wrigleyville Stay
7 adults
2 bedrooms
4 beds
Map4.8 mi from City Centre700 yd from Wrigley Field
FromUS$ 600 /nightSelect
City Villa Sleeps 10-20 Free Tv & Parking
Map4.4 mi from City Centre1700 yd from Wrigley Field
FromUS$ 955 /nightSelect
Walker'S Paradise 1Br Apartment In Lincoln Park - Lincoln 2501
2 adults
2 bedrooms
1 bed
MapCharming Lincoln Park neighborhood200m
  • Full kitchen with cookware and utensils
  • Air conditioning for comfortable stays
  • Flat-screen TV for entertainment
  • On-site parking
  • Air conditioning
  • Flat-screen TV
Urban hotel featuring vibrant local shops and cafes
FromUS$ 64 /nightSelect
Iklektik House // Bluejay
Map2.7 mi from City Centre1.0 mi from United Center
FromUS$ 207 /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
Chic & Fully Furnished 2Br Apartment - Roscoe 1
Map6.4 mi from City Centre800 yd from Addison Station (Blue Line)
FromUS$ 68 /nightSelect
2-Bedroom Cozy Apt In Prime Location - Clark 2
Map7.1 mi from City Centre1000 yd from Berwyn
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Bootlegger House Sleeps 10-20 Free Tv & Parking
Map4.4 mi from City Centre1700 yd from Wrigley Field
FromUS$ 265 /nightSelect

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Check-in
29Jan2026Select date
Check-out
30Jan2026Select date
Rooms and Guests2 Guests, 1 Room