Vacation rentals in Chicago, United States - page 21

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.
View map
401-420 out of 603
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Luxury 6Br Suite Prime South Loop Perfect Location For Families Or Groups Near Soldier Field, Museum Campus & Mccormick Place Chicago
MapNear Museum Campus300m
  • Spacious six-bedroom family suite
  • City views from the living room
  • Fitness centre on site
  • Fitness centre
  • Luggage storage
  • Private parking
Hotel ideal for large families or group stays
FromUS$ 1 076 /nightSelect
Group-Friendly 6Br Luxury Suite In Prime South Loop Location With Optional Parking And Gym Access Near Mccormick Place, Soldier Field And Grant Park Chicago
MapNear McCormick Place200m
  • Six bedrooms for large groups
  • On-site fitness center available
  • City views from spacious patio
  • Optional Parking
  • Fitness Center
  • Luggage Storage
Luxury hotel suite designed for group accommodations
FromUS$ 1 076 /nightSelect
Massive 6Br Luxury Suite Sleeps 12 Guests With Jacuzzi & Pool Table Perfect Group Stay And Optional Parking Near Mccormick Place & Soldier Field
MapNear McCormick Place300m
  • Jacuzzi and pool table available
  • Spacious 6-bedroom luxury suite
  • Private parking on site
  • Jacuzzi
  • Billiards
  • Fitness Centre
Luxury hotel perfect for groups and gatherings
FromUS$ 1 054 /nightSelect
Downtown Chicago 2Br Getaway South Loop Comfort Near Mccormick Place, Soldier Field And Grant Park
MapNear McCormick Place2.3km
  • Modern fitness centre available for guests
  • Well-equipped kitchen for convenient dining
  • Private parking onsite for added convenience
  • Fitness Centre
  • Air Conditioning
  • Private Parking
Hotel near major Chicago attractions and conveniences
FromUS$ 418 /nightSelect
Spacious 2Br On Michigan Ave With Private Patio, Optional Parking & Gym Near Mccormick Convention Center, Soldier Field And Grant Park
MapNear Grant Park2.7km
  • Private patio with city views
  • Fully equipped kitchen available
  • On-site fitness center access
  • Private patio
  • Fitness center
  • Optional parking
Urban hotel featuring modern amenities and private outdoor space
FromUS$ 1 103 /nightSelect
Chicago 2Br City Retreat With Optional Parking And Gym Access Near Mccormick Place And Soldier Field
MapNear McCormick Place300m
  • Spacious rooms with city views
  • On-site fitness centre available
  • Optional parking for convenience
  • Fitness centre
  • Optional parking
  • City views
Hotel offering family-friendly amenities and gym access
FromUS$ 496 /nightSelect
Mccormick 2Br-2Ba For 8 Guests With Optional Parking & Gym
MapField Museum Of Natural History2.3km
  • Fitness centre available on-site
  • Two bedrooms and two bathrooms
  • Optional parking for convenience
  • Fitness centre
  • Air conditioning
  • Optional parking
Hotel offering spacious family-friendly rooms in Chicago
FromUS$ 1 678 /nightSelect
Cozy 3Br City Living In South Loop Near Mccormick Place, Soldier Field & Lakefront
MapNear McCormick Place300m
  • Fitness centre for guest use
  • Rooms with city views and patios
  • Pets allowed in non-smoking rooms
  • Fitness centre
  • Private parking
  • Luggage storage
Hotel offering modern amenities with spacious city rooms
FromUS$ 512 /nightSelect
Spacious 1Br With Optional Parking Near Mccormick Place, Field Museum, Adler Planetarium, & Shedd Aquarium
MapSouth Loop neighborhood near attractions300m
  • Air-conditioned rooms with private entrance
  • Fully equipped kitchen for self-catering
  • Optional parking available on-site
  • Private parking
  • Fully equipped kitchen
  • Air conditioning
Modern apartment with essential amenities in Chicago
FromUS$ 311 /nightSelect
Luxury 5Br South Loop Suite With Pool Table And Optional Parking Near Mccormick Place, Field Museum And Soldier Field
MapNear McCormick Place300m
  • Spacious 5-bedroom rooms for large groups
  • On-site billiards table for entertainment
  • Optional private parking available on-site
  • Billiards Table
  • Parking Available
  • Luggage Storage
Hotel featuring large family-friendly rooms with leisure activities
FromUS$ 869 /nightSelect
Family And Group Friendly 5Br Spacious Unit With Pool Table And Optional Parking Near Mccormick Place And Soldier Field
MapHistoric Printers Row0m
  • Spacious 5 bed family unit available
  • On-site billiards for entertainment
  • Private parking for guests included
  • Billiards table
  • Private parking
  • Air conditioning
Family-oriented hotel with billiards and parking options
FromUS$ 576 /nightSelect
Huge 4Br With Pool Table Chicago Downtown Retreat Good For Groups Sleeps 10 Near Mccormick Place And Field Museum
MapSouth Loop neighborhood300m
  • 4 stylish bedrooms for up to 10 guests
  • Fully equipped kitchen with modern appliances
  • Private parking available on site
  • Fully equipped kitchen
  • Private parking
  • Air conditioning
Large family-friendly apartment near popular attractions
FromUS$ 693 /nightSelect
Bright South Loop 3Br Escape With Pingpong Table And Optional Parking Minutes To Art Institute, Grant Park & Mccormick Place Events
MapClose to Grant Park2.7km
  • Spacious 3-bedroom family room
  • On-site table tennis activities
  • Optional parking available
  • Table Tennis
  • Parking
  • Air Conditioning
Family-friendly hotel with spacious rooms and activities
FromUS$ 527 /nightSelect
River North 1Br W Gym Pool Nr Riverwalk L Chi-1034
Map2.2 km from City Centre1.2 km from Chicago Riverwalk
Select
Stylish 420 Friendly 3Br Suite Near Soldier Field And Mccormick Place
MapNear Soldier Field300m
  • Spacious three-bedroom suite
  • Fully equipped kitchen available
  • Private entrance for added privacy
  • Private parking
  • Air conditioning
  • Flat-screen TV
Modern hotel suite designed for family stays
FromUS$ 700 /nightSelect
Modern 420 Friendly 3Br Apartment In State Street Near Mccormick Place, Chinatown And Soldier Field
MapNear McCormick Place2.4km
  • Three-bedroom modern apartment in South Loop
  • Air-conditioned rooms with full kitchen
  • Luggage storage and private parking available
  • Private parking
  • Fully equipped kitchen
  • Air conditioning
Modern hotel apartment in vibrant Chicago neighborhood
FromUS$ 443 /nightSelect
Luxury 5Br Chicago Retreat Perfect For Groups With Pool Table & Optional Parking Near Mccormick Place And Soldier Field
MapNear historic Printers Row300m
  • Five king bedrooms available
  • Pool table for entertainment
  • Private parking is optional
  • Pool table
  • Private parking
  • Air conditioning
Well-appointed hotel featuring five king bedrooms and entertainment options
FromUS$ 575 /nightSelect
Cozy Chicago 420 Friendly 3Br Suite Near Mccormick Place And Soldier Field
MapNearby Adler Planetarium300m
  • Spacious 3-bedroom suite with full kitchen
  • Private entrance for added privacy
  • Located near McCormick Place and Soldier Field
  • Private parking
  • Air conditioning
  • Flat-screen TV
Hotel featuring a comfortable and private suite experience
FromUS$ 298 /nightSelect
Spacious 420- Friendly 3Br Chicago Apartment With Optional Parking Near Mccormick Place, Soldier Field & Uic Campus
MapField Museum of Natural History200m
  • Spacious 3-bedroom apartments available
  • Private entrance for added privacy
  • Air conditioning for comfort
  • Air Conditioning
  • Private Parking
  • Flat-Screen TV
Hotel offering spacious accommodations near attractions
FromUS$ 495 /nightSelect
Mccormick Place Charming 420 Friendly 3Br Suite With Optional Parking Sleeps 8 Guests Near Soldier Field And Lakefront Trail
MapNear Field Museum Of Natural History2.4km
  • Air-conditioned rooms with flat-screen TV
  • Fully equipped kitchen with dishwasher
  • Optional parking for numerous guests
  • Parking available
  • Fully equipped kitchen
  • Luggage storage
Family-friendly hotel with multiple bedrooms and amenities
FromUS$ 476 /nightSelect
Check-in
19Oct2025Select date
Check-out
20Oct2025Select date
Rooms and Guests2 Guests, 1 Room