Vacation rentals in Chicago, United States

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.
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8.8
Great
5430 Happy Home Chicago
The largest option:
2 adults
1 bedroom
1 bed
MapNext to metro station50m
  • Yoga classes available on-site
  • Shared kitchen facilities for guests
  • Private entrance in select rooms
  • Shared kitchen
  • Yoga classes
  • Private entrance
Homestay with unique amenities in vibrant Chicago
FromUS$ 29 /nightSelect
Luxery Stay Chicago - Themed Units! Close To Downtown, Mccormick Place & Wintrust Arena
MapClose to McCormick Convention Center300m
  • Private beach area for relaxation
  • Fitness centre with yoga classes
  • Family-friendly themed units available
  • Private Beach
  • Fitness Centre
  • Yoga Classes
Themed hotel with beachfront access and family amenities
FromUS$ 243 /nightSelect
2F Chicago'S Little Italy Near West Loop & Downtown
MapBustling Italian Food festival nearby300m
  • Quiet location with spacious rooms
  • Well-equipped kitchen for family meals
  • Close to local attractions and events
  • Fully equipped kitchen
  • Private parking
  • On-site coffee shop
Charming hotel offering modern urban living experience
FromUS$ 215 /nightSelect
1549 North Maplewood Avenue
4 adults
2 bedrooms
3 beds
MapProximity to train station300m
  • On-site spa for relaxation and rejuvenation
  • Fully equipped kitchenette in each room
  • Close to train station for easy travel
  • On-site spa
  • Kitchenette
  • Flat-screen TV
Hotel offering spa services and kitchen facilities
FromUS$ 133 /nightSelect
Perfect Place To Enjoy The City Or Just Relax
The largest option:
4 adults
1 bedroom
2 beds
MapClose to the center8km
  • Air-conditioned rooms with streaming services
  • Historic building with private entrance
  • Fully equipped kitchen and living room
  • Flat-screen TV
  • Fully equipped kitchen
  • Private entrance
Hotel rooms in a historic setting near downtown attractions
FromUS$ 107 /nightSelect
Chicago Charm
Map13.6 km from City Centre400 m from Hoyne Avenue Fields
FromUS$ 266 /nightSelect
Red Robin Rentals - Wicker Park
Map5.4 km from City Centre1000 m from Western Station (O Hare Branch)
FromUS$ 186 /nightSelect
Lincoln Park Apartment With Backyard!
MapLincoln Park Neighborhood600m
  • Proximity to Lincoln Park Zoo
  • Outdoor dining area with garden views
  • Children's play area for family fun
  • Outdoor dining
  • Children's area
  • Garden views
Modern hotel with family-friendly outdoor amenities
FromUS$ 174 /nightSelect
Aurelien Spacious Apartments In The Heart Of Gold Coast
MapMagnificent Mile400m
  • Rooftop pool with stunning views
  • Air-conditioned rooms with kitchen
  • 24-hour front desk for convenience
  • Rooftop pool
  • Fitness centre
  • Outdoor fireplace
Hotel with luxurious amenities in a vibrant area
FromUS$ 266 /nightSelect
Superior
8 adults
3 bedrooms
4 beds
MapWest Town neighborhood dining200m
  • Spacious rooms with city views
  • Outdoor patio and barbecue facilities
  • Equipped kitchen for convenient dining
  • Outdoor dining
  • Equipped kitchen
  • City views
Hotel offering modern amenities and a vibrant locale
FromUS$ 764 /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
K2 Sky High Apartments With Stunning Chicago Views In West Loop
MapWest Loop dining and entertainment300m
  • Rooftop pool with skyline views
  • Air-conditioned rooms with kitchens
  • Spa facilities including hot tub
  • Rooftop pool
  • Outdoor terrace
  • Hot tub
Luxury hotel with stunning views and modern amenities
FromUS$ 283 /nightSelect
Prime Location! - 1 Min Walk To Wrigley Field - 2Br Apts Perfect For Cubs Fans!
The largest option:
5 adults
2 bedrooms
2 beds
MapNear Wrigley Field100m
  • Ideal for Cubs fans and baseball lovers
  • Fully equipped kitchen for family meals
  • Private entrance for added convenience
  • Air Conditioning
  • Flat-Screen TV
  • 24-Hour Security
Apartment-style hotel near Wrigley Field for fans
FromUS$ 82 /nightSelect
Adorable 2 Bedroom With Free Street Parking
Map6.1 km from City Centre200 m from Kedzie (Pink Line)
FromUS$ 100 /nightSelect
Forrestville Ave Large Suite
8 adults
2 bedrooms
2 beds
Map7.4 km from City Centre700 m from 47th Station (Green Line)
FromUS$ 152 /nightSelect
1F Cozy Home In Little Italy Near Downtown West Loop United Center
Map2.2 km from City Centre1.3 km from United Center
FromUS$ 213 /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
Drexel Apartments, Downtown Hyde Park
Map8.6 km from City Centre200 m from Roberts University Assoc
FromUS$ 50 /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$ 235 /nightSelect
Pulaski Point Properties
Map11.2 km from City Centre200 m from Irving Park Station (Blue Line)
FromUS$ 53 /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$ 29
đź’¸ Average price for
Apartments
US$ 431

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:
Days Inn Melrose Park/O'Hare South
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.

Check-in
19Oct2025Select date
Check-out
20Oct2025Select date
Rooms and Guests2 Guests, 1 Room