Vacation rentals in Chicago, United States

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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Adorable 2 Bedroom With Free Street Parking Chicago
Map3.8 mi from City Centre200 yd from Kedzie (Pink Line)
FromUS$ 175 /nightSelect
Lincoln Park 3 Bedroom Penthouse Chicago
MapQuaint Lincoln Park neighborhood2.4km
  • On-site golf course available
  • Walking tours exploring local culture
  • Children's play area on-site
  • On-site Spa
  • Golf Course
  • Bar Crawls
Luxury hotel offering stylish leisure and family amenities
FromUS$ 116 /nightSelect
Wrigley Oasis! Steps From The Field! - 3Bd 1Ba
4 adults
3 bedrooms
3 beds
MapWrigleyville neighborhood400m
  • Three bedrooms for family stays
  • Outdoor dining area for relaxation
  • Access to Wrigley Field nearby
  • Outdoor dining
  • Flat-screen TV
  • Fully equipped kitchen
Hotel offering comfortable rooms near Wrigley Field
FromUS$ 400 /nightSelect
Chic Retreat
Map10.8 mi from City Centre500 yd from Chicago State University
FromUS$ 220 /nightSelect
Boho Bliss - 1Br, 1Bath W/Patio!
Map4.3 mi from City Centre500 yd from Gold Domino Social Club
FromUS$ 197 /nightSelect
The Lyons' Lair
Map5.8 mi from City Centre1.2 mi from Wrigley Field
FromUS$ 396 /nightSelect
Chicago Exquisite Haven 2Bed 2Bath Near Downtown And United Center
Map2.6 mi from City Centre1700 yd from United Center
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2-Bed 2-Bath Apt - Close To Uc W/ Free Parking
Map2.2 mi from City Centre800 yd from United Center
FromUS$ 130 /nightSelect
Cozy & Modern 3Br Apartment - Division 201W 301W Rep
MapVibrant neighborhood atmosphere300m
  • Modern flat-screen TV available
  • Comfortable air conditioning provided
  • On-site dryer for guest use
  • Flat-screen TV
  • Air conditioning
  • On-site dryer
Urban apartment offering modern amenities and convenience
FromUS$ 281 /nightSelect
Condo Apartment Near Midway Airport
Map7.7 mi from City Centre1100 yd from Midway Airport (MDW)
FromUS$ 142 /nightSelect
Wrigley Garden Unit
5 adults
3 bedrooms
3 beds
MapClose to Wrigley Field700m
  • Rooms with garden views and private entrance
  • Close to Wrigley Field and Fullerton Beach
  • Air-conditioned with flat-screen TV
  • Private Parking
  • Air Conditioning
  • Pet Friendly
Charming hotel near attractions with spacious rooms
FromUS$ 124 /nightSelect
Stunning 2 Floor Penthouse Downtown
Map1.9 mi from City Centre600 yd from Chicago Station (Blue Line)
FromUS$ 1 147 /nightSelect
Beautiful Big 3 Bedroom Quiet Apt Near Downtown
Map9.1 mi from City Centre600 yd from MC Coy Barber College
FromUS$ 369 /nightSelect
Retro 2 Bedroom Home 6 Mins To United Center With Parking
Map4.2 mi from City Centre700 yd from Pulaski Station (Blue Line)
FromUS$ 250 /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$ 601 /nightSelect
Cozy & Near Downtown & Hyde Park
Map8.6 mi from City Centre700 yd from Jackson Park Hosp & Med Ctr
FromUS$ 108 /nightSelect
Modern 2Br In South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail
MapHistoric Printers Row300m
  • Optional parking available on site
  • Access to fitness center amenities
  • Pet-friendly environment for travelers
  • Fitness Centre
  • Parking Available
  • Terrace Views
Hotel with versatile amenities in vibrant South Loop
FromUS$ 305 /nightSelect
Fully Furnished 2Br Apartment Near Oak Park I Utilities Included I Car Rental Available
Map6.8 mi from City Centre1300 yd from
FromUS$ 161 /nightSelect
Stylish And Expansive 2Br Apt With Balcony - Buckingham 3
MapHome of Wrigleyville300m
  • Large balcony for outdoor relaxation
  • Flat-screen TV in stylish living area
  • Pet-friendly rooms for traveling companions
  • Flat-screen TV
  • Pet-friendly
  • Balcony view
Modern hotel offering expansive rooms in vibrant neighborhood
FromUS$ 314 /nightSelect
Hyde Park Modern Private Room - Near Univ Of Chicago
2 adults
1 bedroom
1 bed
MapNearby 47th Subway Station200m
  • Modern rooms with garden view
  • Satellite flat-screen TV included
  • Shared kitchen facilities available
  • Garden view
  • Shared kitchen
  • Air conditioning
Modern hotel with convenient access to cultural attractions
FromUS$ 82 /nightSelect

Flexible Price Range for Vacation Homes in Chicago

From cozy retreats to luxury villas – Find the ideal stay for every budget

⬆️ The highest price
US$ 2 390
⬇️ The lowest price
US$ 9
đź’¸ Average price for
Apartments
US$ 433

Top vacation homes in Chicago

Based on guest reviews from the past 12 months

Cultural Hotspots in Little Italy:
2F Chicago'S Little Italy Near West Loop & Downtown
Convenient Airport Access:
Homey Retreats in the City:
5430 Happy Home
Urban Living with Style:

How to get to Chicago

Explore local transportation options with ease

Airports
Chicago O'Hare International Airport (ORD)
Chicago Midway International Airport (MDW)

FAQs about Chicago rentals

Get answers to common questions and plan your adventure smoothly

What are the cheapest vacation rental options in Chicago?
Affordable choices include properties like 'Cozy 1 Bedroom, 1 Min From Irving Park Blue Line, Free Parking' and 'Convenient & Newly Decorated 1Br Apartment - Roscoe 1D', which typically range from $80 to $120 per night.

Vacation Rentals Insights in Chicago

This guide evaluates various vacation rentals in Chicago, reviewing 7 properties to provide crucial information for your travel planning, including pricing, local fees, and prime locations.

Typical nightly rates range from $100 to $300 USD.

Peak seasons include summer (June to August) and holidays.

Local taxes and fees can add around 17% to total booking costs.

Key attractions like Millennium Park are about 1.5 miles from downtown rentals.

Book early-3 to 6 months ahead-for the best options.

Other cities in United States

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