Vacation rentals in Chicago, United States

Carefully selected & verified rentals in Chicago, United States
Check-in
26Aug2025Select date
Check-out
27Aug2025Select 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
41-60 out of 214
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Retro 2 Bedroom Home 6 Mins To United Center With Parking Chicago
Map4.2 mi from City Centre700 yd from Pulaski Station (Blue Line)
FromUS$ 259 /nightSelect
The Banksy-Free Parking -4 Bedroom W King Bed- Firepit Rooftop Near United Center Chicago
Map2.3 mi from City Centre1100 yd from United Center
FromUS$ 1 313 /nightSelect
The Roscoe Village Guesthouse
Map5.0 mi from City Centre700 yd from Paulina
FromUS$ 282 /nightSelect
Flexhome Avondale 2Br Apt W1 With Parking
Map5.5 mi from City Centre
FromUS$ 181 /nightSelect
Lakeview East Apartment
Map4.2 mi from City Centre1700 yd from Wrigley Field
Select
Great Chicago Getaway 2 Bedrooms Sleeps 1 To 4
Map5.9 mi from City Centre1200 yd from Michelle's Ballroom
Select
City Villa Sleeps 10-20 Free Tv & Parking
Map4.4 mi from City Centre1700 yd from Wrigley Field
FromUS$ 690 /nightSelect
Charming 3Bd 2Bth Apartment
Map7.3 mi from City Centre1100 yd from King Drive
FromUS$ 64 /nightSelect
Chic Euro City Getaway- Close To Downtown
Map5.0 mi from City Centre400 yd from 51st
FromUS$ 198 /nightSelect
The Bright Retreat In Andersonville
MapFoster Beach1.6km
  • Air-conditioned rooms with a flat-screen TV
  • Fully equipped kitchen for home cooking
  • Private parking available on site
  • Private parking
  • Fully equipped kitchen
  • Flat-screen TV
Cozy apartment-style hotel with convenient amenities
FromUS$ 215 /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
15 Minutes Ohare & Downtown2
Map9.5 mi from City Centre1000 yd from Jefferson Park
FromUS$ 319 /nightSelect
The Haven, Great Location Near Downtown, Medical District And United Center
Map2.6 mi from City Centre1700 yd from United Center
FromUS$ 392 /nightSelect
Mixed Rustic Vibes
Map3.1 mi from City Centre900 yd from Kedzie-Homan
Select
Well-Appointed Cozy Portage Park Apt, Dogs, Kids, Free Parking, 420 Compliant
MapProximity to Wrigley Field11km
  • Spacious apartment with three bedrooms
  • Indoor play area for children
  • Pets allowed with outdoor dining area
  • Fully equipped kitchen
  • Private entrance
  • Children's play area
Family-friendly apartment with pet access and outdoor space
FromUS$ 101 /nightSelect
Wrigleyville Home Away From Home! 5 Mins From Downtown! Steps From Lake!! Cozy!
MapSteps from Montrose Beach1.8km
  • Spacious 3-bedroom rooms available
  • Access to balcony and patio areas
  • Fully equipped kitchen with appliances
  • Fully equipped kitchen
  • Private parking
  • Flat-screen TV
Modern apartment-style hotel near lake and park
Select
Flexhome Avondale 3Br Duplex Apt W2
Map5.5 mi from City Centre
FromUS$ 143 /nightSelect
Bootlegger House Sleeps 10-20 Free Tv & Parking
Map4.4 mi from City Centre1700 yd from Wrigley Field
FromUS$ 265 /nightSelect
First Floor Condo In Chicago
MapNear Cloud Gate - The Bean6.6km
  • Rooms with a spa bath
  • Fully equipped kitchen available
  • Private parking on site
  • Spa bath
  • Private parking
  • Cable TV
Condo with fully equipped kitchen in Chicago's heart
FromUS$ 312 /nightSelect
Comfy Retreat In Rogers Park, Prime Location!
Map8.8 mi from City Centre300 yd from Hoyne Avenue Fields
FromUS$ 283 /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$ 2 453
⬇️ The lowest price
US$ 29
đź’¸ Average price for
4-star hotels
US$ 279
Apartments
US$ 306

Top vacation homes in Chicago

Based on guest reviews from the past 12 months

Vibrant Wrigleyville Escapes:
Cultural Hotspots in Little Italy:
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.
Which vacation rentals in Chicago are located close to major attractions?
The 'Double Play Wrigley - Prime Location! - 1 Min Walk To Wrigley Field' is conveniently located near Wrigley Field. Similarly, 'Chicago 2Br Suite Perfect For Convention And Business Trips' is near McCormick Place and other central attractions.
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
26Aug2025Select date
Check-out
27Aug2025Select date
Rooms and Guests2 Guests, 1 Room