Vacation rentals in Chicago, United States - page 3

Carefully selected & verified rentals in Chicago, United States
Check-in
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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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41-60 out of 603
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La Villita - Gateway To Chicago Apartment
Map6.2 km from City Centre800 m from Kedzie (Pink Line)
FromUS$ 203 /nightSelect
Trendy West Town Flat - 2 Bed / 1.5 Bath W Parking Apartment Chicago
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
Modern 3 Bedroom Close To Downtown Chicago
Map6.4 km from City Centre200 m from Indiana
FromUS$ 87 /nightSelect
Spacious Historic Apartments In Lakeview Chicago - Walk To Wrigley, Nightlife, Shops, Hospitals
MapNear Wrigley Field1.2km
  • Historic charm and modern amenities
  • Fully equipped kitchens available
  • Family-friendly with outdoor gardens
  • Air conditioning
  • Family rooms
  • Outdoor dining
Hotel featuring historic architecture and family-friendly accommodations
FromUS$ 238 /nightSelect
Chicago Exquisite Haven 2Bed 2Bath Near Downtown And United Center
Map4.2 km from City Centre1.5 km from United Center
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Modern 2Br 420 Friendly In Chicago South Loop Near Museum Campus, Mccormick Place And Soldier Field
6 adults
2 bedrooms
3 beds
MapClose to public transport stops200m
  • Cozy 420 friendly rooms available
  • Fully equipped kitchen for cooking
  • Private parking available on request
  • Air Conditioning
  • Flat-screen TV
  • 24-hour Security
Cozy hotel near vibrant attractions with parking options
FromUS$ 236 /nightSelect
Cozy Luxury Apt~ Near Uchicago/Hydepark/Lakeshore
Map10.6 km from City Centre
FromUS$ 150 /nightSelect
Cozy 2 Brm Apartment Mins Away From United Center
Map4.7 km from City Centre1.8 km from United Center
FromUS$ 181 /nightSelect
A Secluded Bedroom With A Private Full Bathroom
Map9.8 km from City Centre300 m from MC Cormick Seminary
FromUS$ 119 /nightSelect
Ideal 3Br Business Or Leisure Rental In Chicago Fully Stocked Kitchen & Fast Internet With Optional Parking Near Soldier Field, Grant Park & Mccormick Place
8 adults
3 bedrooms
4 beds
MapHistoric Printers Row300m
  • Three bedrooms for comfortable group stays
  • Features a fitness centre for active guests
  • Private entrance and soundproofing for privacy
  • Fitness Centre
  • Private Entrance
  • City Views
Designer suite ideal for families and groups in Chicago
FromUS$ 976 /nightSelect
1Br Modern Apartment In Lincoln Square - Eastwood 3S Rep
2 adults
1 bedroom
1 bed
Map10.7 km from City Centre300 m from Western Station (Brown Line)
FromUS$ 201 /nightSelect
Flexhome Avondale 2Br Apt W1 With Parking
Map8.9 km from City Centre
FromUS$ 181 /nightSelect
Chicago Vacation Rental Near Lake Michigan!
Map5.0 km from City Centre
FromUS$ 203 /nightSelect
The Avondale Attic
MapNearby Wrigley Field4.6km
  • Fully equipped kitchen available
  • Flat-screen TV with streaming services
  • Air-conditioned spacious rooms
  • Air conditioning
  • Flat-screen TV
  • Fully equipped kitchen
Unique hotel featuring spacious apartment-style rooms
FromUS$ 102 /nightSelect
Cozy Chicago Apartment Next To The River
Map4.3 km from City Centre400 m from Ashland (Orange Line)
FromUS$ 226 /nightSelect
Mccormick Place 2Br Stylish Suite With Optional Parking And Gym For Up To 8 Guests Near Soldier Field And Grant Park
Map2.7 km from City Centre700 m from McCormick Place
FromUS$ 369 /nightSelect
Avra Stylish Apartments Prime West Loop Location Near Union Park
MapNear popular dining options200m
  • Fully equipped kitchen in every room
  • Fitness centre available for guests
  • Sunny terrace for outdoor relaxation
  • Fitness Centre
  • Sun Terrace
  • Private Parking
Hotel offering stylish rooms with convenient amenities
FromUS$ 115 /nightSelect
Webster House
3 adults
1 bedroom
2 beds
Map5.1 km from City Centre300 m from Lincoln Park Hospital
FromUS$ 232 /nightSelect
Spacious 2Br Vacation Rental With City View, Optional Parking And Gym Near Mccormick Place & Downtown Chicago Attractions
MapHistoric Printers Row0m
  • Gym access for guests
  • Rooms with city views
  • Full kitchen amenities
  • Fitness Centre
  • City View
  • Parking Available
Urban hotel with flexible rooms for families and groups
FromUS$ 360 /nightSelect
Check-in
19Oct2025Select date
Check-out
20Oct2025Select date
Rooms and Guests2 Guests, 1 Room