Vacation rentals in Chicago, United States

Carefully selected & verified rentals in Chicago, United States
Check-in
06Dec2025Select date
Check-out
07Dec2025Select 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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1-20 out of 690
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Red Robin Rentals - Wicker Park Chicago
Map5.4 km from City Centre1000 m from Western Station (O Hare Branch)
FromUS$ 164 /nightSelect
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
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
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
Gorgeous 4Bdr In Chicago,15Mins From Dwtn
Map14.9 km from City Centre800 m from Jazz Unites Inc
FromUS$ 289 /nightSelect
Modern 2Br Loft With Amazing City Skyline View And Optional Parking For 8 Guests Near Mccormick Place And Soldier Field
4 adults
2 bedrooms
3 beds
MapSouth Loop neighborhood200m
  • Amazing city skyline views from rooms
  • Fitness centre available on-site
  • Optional parking for up to 8 guests
  • Fitness Centre
  • Parking Available
  • 24-Hour Security
Modern loft-style hotel featuring skyline views and fitness amenities
FromUS$ 459 /nightSelect
Forrestville Ave Large Suite
8 adults
2 bedrooms
2 beds
Map7.4 km from City Centre700 m from 47th Station (Green Line)
FromUS$ 188 /nightSelect
Condo Apartment Near Midway Airport
Map12.3 km from City Centre1000 m from Midway Airport (MDW)
FromUS$ 142 /nightSelect
The Lyons' Lair
Map9.3 km from City Centre1.9 km from Wrigley Field
FromUS$ 396 /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
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
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
Cozy 2 Brm Apartment Mins Away From United Center
Map4.7 km from City Centre1.8 km from United Center
FromUS$ 181 /nightSelect
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$ 467 /nightSelect
1Br Stylish Apartment, Perfect For Getaway - Oakdale 201
5 adults
1 bedroom
1 bed
Map6.6 km from City Centre1.8 km from Wrigley Field
FromUS$ 64 /nightSelect
Entire Modern 2 Bedroom Apartment
4 adults
2 bedrooms
3 beds
MapNear Wrigley Field9km
  • Two bedrooms with private entrance
  • Flat-screen TV with streaming services
  • On-site private parking available
  • Private parking
  • Air conditioning
  • Garden space
Stylish apartment hotel near major Chicago attractions
FromUS$ 79 /nightSelect
Beautiful Big 3 Bedroom Quiet Apt Near Downtown
Map14.6 km from City Centre
FromUS$ 216 /nightSelect
Retro 2 Bedroom Home 6 Mins To United Center With Parking
Map6.8 km from City Centre600 m from Pulaski Station (Blue Line)
FromUS$ 444 /nightSelect
A Secluded Bedroom With A Private Full Bathroom
Map9.8 km from City Centre300 m from MC Cormick Seminary
FromUS$ 133 /nightSelect
Comfy & Modern 3Br Home Free Wifi Free Parking
Map3.8 km from City Centre1.4 km from United Center
FromUS$ 235 /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$ 4 031
⬇️ The lowest price
US$ 9
đź’¸ Average price for
Apartments
US$ 409

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 (ORD)
Midway International (MDW)

FAQs about Chicago rentals

Get answers to common questions and plan your adventure smoothly

Which vacation rentals in Chicago are best for families with children?
Properties like 'Wrigley Oasis! Steps From The Field! - 3Bd 1Ba' and 'Wrigleyville Friends Unit - 5Bdrm' are spacious and family-friendly with amenities to accommodate larger groups.
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
06Dec2025Select date
Check-out
07Dec2025Select date
Rooms and Guests2 Guests, 1 Room