Vacation rentals in Chicago, United States - page 8

Carefully selected & verified rentals in Chicago, United States
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Check-out
31Jan2026Select 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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141-160 out of 620
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Modern & Furnished 2Br Apt With In-Unit Laundry - Sunnyside 2E Chicago
Map8.5 mi from City Centre1100 yd from Jefferson Park
FromUS$ 79 /nightSelect
Stylish & Bright Gem Overlooks Lovely Park With Great Amenities Chicago
Map5.8 mi from City Centre700 yd from Animal Kingdom Inc
FromUS$ 201 /nightSelect
Style & Serene In Jefferson Park Close To Dwtwn & Ord Unit 2
Map9.5 mi from City Centre1000 yd from Jefferson Park
FromUS$ 114 /nightSelect
Inspiring Grotto Sleeps 10-20 Free Tv & Parking
Map4.4 mi from City Centre1700 yd from Wrigley Field
FromUS$ 498 /nightSelect
Stone Mansion Sleeps 10-20 Free Tv & Parking
Map4.4 mi from City Centre1700 yd from Wrigley Field
FromUS$ 1 186 /nightSelect
Apartment Sleeps 4 With Free Parking
Map9.5 mi from City Centre1000 yd from Jefferson Park
FromUS$ 319 /nightSelect
Perfect Stay - Modern 2Br Unit - Barry Gb
Map4.3 mi from City Centre1300 yd from Wrigley Field
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The Wrigleyville Deluxe -Steps From Wrigley Sleeps 10
MapWrigley Field300m
  • Walking distance to Wrigley Field
  • Five bedrooms for larger groups
  • Fully equipped kitchen available
  • Air conditioning
  • Flat-screen TV
  • Free parking
Hotel for group stays near Chicago's Wrigley Field
FromUS$ 697 /nightSelect
2Br Enticing Apt In Chicago Near Restaurants - Belmont A2 A4 Rep
MapLakeview neighborhood0m
  • Modern kitchen with essential appliances
  • Flat-screen TV for entertainment
  • Two bedrooms for family or friends
  • Flat-screen TV
  • Seating area
  • Dishwasher
Apartment offering convenient access to Chicago's dining
FromUS$ 66 /nightSelect
1Br Calm & Cozy Apt In Lincoln Square - Eastwood 2S
Map6.6 mi from City Centre300 yd from Western Station (Brown Line)
FromUS$ 274 /nightSelect
Alluring Studio Apartment In Jefferson Park - Leland 1N
MapDynamic Jefferson Park area1.2km
  • Flat-screen TV for entertainment
  • No smoking on site for comfort
  • On-site dryer for convenience
  • Flat-screen TV
  • On-site dryer
  • No smoking
Hotel offering studio rooms in a vibrant neighborhood
FromUS$ 182 /nightSelect
1Br Tranquil & Airy Apartment In Lincoln Square - Campbell Rep
2 adults
1 bedroom
1 bed
MapVibrant local shopping area300m
  • Airy rooms with natural lighting
  • Fully equipped kitchen available
  • Tranquil setting in Lincoln Square
  • Flat-screen TV
  • Dryer
  • Kitchen utensils
Hotel featuring rejuvenating atmosphere with local charm
FromUS$ 256 /nightSelect
1Br Modern Lakeview Apt Close To Dining - Oakdale 2S
2 adults
1 bedroom
1 bed
MapProximity to North Avenue Beach3km
  • Modern air-conditioned rooms with lake views
  • Close to local dining and entertainment options
  • Flat-screen TV available for guest use
  • Paid parking
  • Air conditioning
  • Flat-screen TV
Modern rooms near recreational and dining areas in Chicago
FromUS$ 159 /nightSelect
Mccormick Place Luxurious And Spacious 3Br In Downtown Chicago With Optional Parking Sleeps 10 Guests
6 adults
3 bedrooms
4 beds
MapProximity to Field Museum200m
  • Three bedrooms and two bathrooms available
  • Optional parking for convenience
  • Fitness center on-site for guests
  • Fitness Centre
  • Air Conditioning
  • 24-hour Reception
Hotel with three bedrooms and downtown accessibility
FromUS$ 1 615 /nightSelect
Cool 2Br Apartment Close To Fun City - Grace 2
5 adults
2 bedrooms
1 bed
MapVibrant Lakeview neighborhood9km
  • Modern flat-screen TV amenities
  • Quiet, smoke-free environment
  • Convenient dryer for guests
  • Flat-screen TV
  • Dryer
  • Smoke-free
Hotel offering chic urban living near entertainment hubs
FromUS$ 557 /nightSelect
Super Amazing Place To Stay Near Downtown! Free Parking
Map4.7 mi from City Centre900 yd from 47th (Red Line)
FromUS$ 99 /nightSelect
Parisian Retreat 6Min To Main Quandrangle U Of C
Map7.1 mi from City Centre500 yd from Cottage Grove
FromUS$ 310 /nightSelect
Quiet 1Br, Eat-In Kitchen, Close To Midway
Map6.6 mi from City Centre1700 yd from Capri Beauty Schools Inc
FromUS$ 194 /nightSelect
Chic 2Br 2Ba Condo With Balcony - River North Chicago
Map1.1 mi from City Centre800 yd from Chicago Riverwalk
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Cosy Room Near Medical District With Private Balcony
Map3.0 mi from City Centre1000 yd from Western Station (Forest Park Branch)
FromUS$ 49 /nightSelect

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Check-in
30Jan2026Select date
Check-out
31Jan2026Select date
Rooms and Guests2 Guests, 1 Room