Vacation rentals in Chicago, United States - page 2

Carefully selected & verified rentals in Chicago, United States
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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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21-40 out of 712
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Chic & Updated Studio Apt In East Lakeview - Barry S1 Chicago
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
Forrestville Ave Large Suite Chicago
8 adults
2 bedrooms
2 beds
Map4.6 mi from City Centre700 yd from 47th Station (Green Line)
FromUS$ 145 /nightSelect
Bridgeport Place - Free Parking, Mccormick Place-Sox Park
Map3.0 mi from City Centre900 yd from Ashland (Orange Line)
FromUS$ 220 /nightSelect
A Secluded Bedroom With A Private Full Bathroom
Map6.1 mi from City Centre300 yd from MC Cormick Seminary
FromUS$ 133 /nightSelect
Foundry Unmatched Skyline Views At Lincoln Park
Map2.3 mi from City Centre500 yd from North/Clybourn
FromUS$ 813 /nightSelect
Stylish 2Br Pad With Up-To-Date Comforts - Halsted Rep
4 adults
2 bedrooms
1 bed
MapLakeview neighborhood6km
  • Modern amenities in a trendy apartment
  • Flat-screen TV for entertainment
  • Cookware and kitchen utensils provided
  • Flat-screen TV
  • Kitchen utensils
  • No pets allowed
Stylish hotel featuring contemporary living spaces and facilities
FromUS$ 197 /nightSelect
A Hidden Gem, Approx 15 Mins To Downtown Chicago!
MapWater Tower Chicago11km
  • Outdoor dining area for guest enjoyment
  • Shared lounge to relax and socialize
  • Fully equipped kitchen for self-catering
  • Shared kitchen
  • Outdoor area
  • Satellite TV
Homestay with relaxed atmosphere and modern amenities
FromUS$ 96 /nightSelect
The Chic Urban Oasis Near The Lake!
MapProximity to Museum of Science and Industry4.5km
  • Close to 63rd Street Beach
  • Spacious rooms with fireplace
  • Golf course onsite for leisure
  • Golf course
  • Air conditioning
  • Flat-screen TV
Hotel with spacious rooms near Chicago's attractions
FromUS$ 136 /nightSelect
The Roscoe Village Guesthouse
Map5.0 mi from City Centre700 yd from Paulina
FromUS$ 282 /nightSelect
Afrique Francaise De Woodlawn 1
Map7.1 mi from City Centre800 yd from King Drive
FromUS$ 32 /nightSelect
Game Day Getaway - 3Br In Vibrant Wrigleyville
Map5.3 mi from City Centre700 yd from Wrigley Field
FromUS$ 252 /nightSelect
Logan Square Modern Apartment
MapLogan Square craft cocktail scene300m
  • Private parking available on site
  • Air-conditioned rooms with balconies
  • Outdoor dining area with garden views
  • Private parking
  • Outdoor dining
  • Flat-screen TV
Stylish urban apartment with outdoor dining space
FromUS$ 165 /nightSelect
Trendy West Town Flat - 2 Bed / 1.5 Bath W Parking
MapVibrant West Town neighborhood1.5km
  • Private parking on-site available
  • Patio for relaxing outdoors
  • Fully equipped kitchen included
  • Private parking
  • Fully equipped kitchen
  • Outdoor patio
Furnished apartment in trendy Chicago neighborhood with amenities
FromUS$ 283 /nightSelect
Bella Villa On Taylor Street Chicago'S Little Italy 1 Mile West The Loop & Uic
Map1.3 mi from City Centre1.0 mi from United Center
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East Village 2Br Modern Apartment H1
MapCharming West Town area1km
  • Modern 2BR apartment with private entrance
  • Fully equipped kitchen for home cooking
  • Located in vibrant West Town neighborhood
  • Air Conditioning
  • Fully Equipped Kitchen
  • Private Entrance
Stylish city apartment in a dynamic urban setting
FromUS$ 156 /nightSelect
City Villa Sleeps 10-20 Free Tv & Parking
Map4.4 mi from City Centre1700 yd from Wrigley Field
FromUS$ 234 /nightSelect
Modern 3Br In South Loop With Optional Parking And Gym Access Near Mccormick Place, Chinatown And Soldier Field
Map1.7 mi from City Centre800 yd from McCormick Place
FromUS$ 247 /nightSelect
The Wrigleyville Vip-200 Steps From Wrigley Field
MapWrigley Field300m
  • Barbecue facilities available for guests
  • Two-bedroom rooms with modern amenities
  • Close to attractions in Wrigleyville area
  • Barbecue Facilities
  • Air Conditioning
  • Golf Course
Hotel featuring residential-style rooms near Wrigley Field
FromUS$ 453 /nightSelect
Superior
8 adults
3 bedrooms
4 beds
MapWest Town neighborhood dining200m
  • Spacious rooms with city views
  • Outdoor patio and barbecue facilities
  • Equipped kitchen for convenient dining
  • Outdoor dining
  • Equipped kitchen
  • City views
Hotel offering modern amenities and a vibrant locale
FromUS$ 764 /nightSelect
The Banksy-Free Parking -4 Bedroom W King Bed- Firepit Rooftop Near United Center
Map2.3 mi from City Centre1100 yd from United Center
FromUS$ 1 384 /nightSelect

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