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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Wrigley Oasis! Steps From The Field! - 3Bd 1Ba Apartment Chicago
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 Apartment Chicago
Map10.8 mi from City Centre500 yd from Chicago State University
FromUS$ 230 /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$ 506 /nightSelect
2-Bed 2-Bath Apt - Close To Uc W/ Free Parking
Map2.2 mi from City Centre800 yd from United Center
FromUS$ 130 /nightSelect
Condo Apartment Near Midway Airport
Map7.7 mi from City Centre1100 yd from Midway Airport (MDW)
FromUS$ 142 /nightSelect
The Penthouse, Lux Stay Near Downtown, Uofc & Lake
Map4.8 mi from City Centre800 yd from Sutherland Community Arts
FromUS$ 240 /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$ 247 /nightSelect
Spacious 5-Br Apt Next To Transit Free Parking
MapUnited Center proximity6.1km
  • Five bedrooms accommodate up to eleven guests
  • Located near public transit options
  • Offers free parking and picnic area
  • Fully Equipped Kitchen
  • Air Conditioning
  • Sun Terrace
Hotel offering family-friendly lodging with modern amenities
FromUS$ 376 /nightSelect
Beautiful Big 3 Bedroom Quiet Apt Near Downtown
Map9.1 mi from City Centre600 yd from MC Coy Barber College
FromUS$ 369 /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
Cozy & Near Downtown & Hyde Park
Map8.6 mi from City Centre700 yd from Jackson Park Hosp & Med Ctr
FromUS$ 108 /nightSelect
Modern 3 Bedroom Close To Downtown Chicago
Map3.9 mi from City Centre200 yd from Indiana
FromUS$ 87 /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$ 444 /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
Penthouse Level, Stunning Wrigley Stay
4 adults
2 bedrooms
3 beds
MapWrigley Field700m
  • Spacious rooms with garden views
  • Private outdoor dining area available
  • Located near Wrigley Field
  • Outdoor dining
  • Sun terrace
  • Picnic area
hotel in vibrant Lakeview near Wrigley Field
FromUS$ 170 /nightSelect
Stylish Urban Retreat 3 Bedroom Newly Remodeled
Map3.9 mi from City Centre200 yd from Indiana
FromUS$ 86 /nightSelect
Forrestville Ave Large Suite
8 adults
2 bedrooms
2 beds
Map4.6 mi from City Centre700 yd from 47th Station (Green Line)
FromUS$ 145 /nightSelect
A Secluded Bedroom With A Private Full Bathroom
Map6.1 mi from City Centre300 yd from MC Cormick Seminary
FromUS$ 133 /nightSelect
2Br Airy & Tidy Apt With Free Covered Parking - Central Modern
6 adults
2 bedrooms
1 bed
MapNearby United Center1.2km
  • Free covered parking available
  • Flat-screen TV in all rooms
  • Cookware and kitchen utensils provided
  • Free Parking
  • Flat-screen TV
  • Kitchen Utensils
Modern hotel with essential amenities for travelers
FromUS$ 205 /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$ 2 198
⬇️ The lowest price
US$ 9
đź’¸ Average price for
Apartments
US$ 408

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.
Are there any vacation rentals in Chicago suited for couples looking for a romantic getaway?
Consider 'Chic Retreat | Fully Equipped Cozy 4/5 Br' or 'Stunning Duplex Condo #1 - Downtown River North' for a cozy yet upscale romantic experience, offering privacy and stylish design.

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
29Jan2026Select date
Check-out
30Jan2026Select date
Rooms and Guests2 Guests, 1 Room