Vacation rentals in Chicago, United States - page 5

Carefully selected & verified rentals in Chicago, United States
Check-in
19Oct2025Select date
Check-out
20Oct2025Select 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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81-100 out of 603
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Ukrainian Village 2Br Modern Apartment D1 Chicago
MapWest Town's dining and boutiques1km
  • 2 Bedrooms with modern amenities
  • Fully equipped kitchen for convenience
  • Non-smoking, family-friendly rooms
  • Fully equipped kitchen
  • Air conditioning
  • Washing machine
Urban retreat with modern apartments in vibrant neighborhood
FromUS$ 224 /nightSelect
6 Mi To Dtwn Pet-Friendly Chicago Condo
Map7.8 km from City Centre
FromUS$ 148 /nightSelect
Uptown Gem
4 adults
1 bedroom
1 bed
MapNear Montrose Beach1.3km
  • Indoor swimming pool and fitness centre
  • Family-friendly restaurant with American cuisine
  • Patio with city views and outdoor dining area
  • Indoor pool
  • Fitness centre
  • Outdoor patio
Hotel with modern rooms and leisure facilities in Chicago
FromUS$ 579 /nightSelect
Modern Belden
Map7.2 km from City Centre
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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
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$ 267 /nightSelect
Townhome
Map11.8 km from City Centre2.0 km from Loyola University Chicago
FromUS$ 81 /nightSelect
Luxurious New Remodeled
Map20.1 km from City Centre300 m from Chip-IN Tours
FromUS$ 127 /nightSelect
1Br Adorable Apt With In-Unit Laundry - Lake 206 Rep
MapAdorable West Loop neighborhood200m
  • Fully equipped kitchen available
  • Modern flat-screen TV provided
  • Non-smoking rooms for comfort
  • Flat-screen TV
  • Air conditioning
  • In-unit washer
Cozy hotel with modern amenities in vibrant setting
FromUS$ 579 /nightSelect
Cozy North Side Oasis
Map6.8 km from City Centre
FromUS$ 331 /nightSelect
Flexhome Avondale 3Br Duplex Apt W2
Map8.9 km from City Centre
FromUS$ 143 /nightSelect
Chic Chicago Apartment About 1 Mi To Wrigley Field!
Map9.1 km from City Centre1.0 km from Wrigley Field
FromUS$ 139 /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
Mccormick Place 420-Friendly 3Br-2Ba With Optional Parking - Sleeps 8
MapHistoric Printers Row300m
  • Soundproof rooms for ultimate privacy
  • Fully equipped kitchen for easy dining
  • Optional parking available on-site
  • Air Conditioning
  • Flat-Screen TV
  • Optional Parking
Hotel featuring fully equipped family-sized apartments
FromUS$ 585 /nightSelect
The Wrigleyville Garden 200 Steps To Wrigley-2Br
MapClose to Wrigley Field300m
  • Air-conditioned, spacious 2-bedroom rooms
  • Flat-screen TV with satellite channels
  • Non-smoking property with free parking
  • Free parking
  • Air conditioning
  • Flat-screen TV
Modern hotel near iconic Wrigley Field in Chicago
FromUS$ 136 /nightSelect
Stunning 1Br Apartment At Center Of Lakeview - Oakdale 211
MapWrigleyville and Chicago Cubs5km
  • Fully equipped kitchen available for cooking
  • Flat-screen TV for entertainment options
  • No smoking allowed on site for comfort
  • Flat-screen TV
  • Kitchen utensils
  • Laundry dryer
Modern hotel near vibrant Wrigleyville and attractions
FromUS$ 74 /nightSelect
Mccormick Place 3Br Luxury Penthouse Duplex With Personal Rooftop And Optional Parking For 8 Guests In Chicago South Loop
The largest option:
8 adults
3 bedrooms
4 beds
MapNear Field Museum Of Natural History2.3km
  • Personal rooftop with stunning views
  • Fully equipped kitchen with modern appliances
  • Fitness centre available for guest use
  • Fitness Centre
  • Private Parking
  • Outdoor Dining
Luxury penthouse with rooftop in vibrant Chicago area
FromUS$ 431 /nightSelect
Sage Modern Apartments Near Union Park In West Loop
Map1.2 km from City Centre1.1 km from Chicago Union Station
FromUS$ 386 /nightSelect
Logan Square Monthly Apartament
Map7.0 km from City Centre
FromUS$ 241 /nightSelect
Mccormick Place Huge 2Br Cozy Loft Suite With Optional Parking Sleeps 8 Near Soldier Field And Grant Park
Map2.7 km from City Centre700 m from McCormick Place
FromUS$ 514 /nightSelect
Check-in
19Oct2025Select date
Check-out
20Oct2025Select date
Rooms and Guests2 Guests, 1 Room