Best price vacation rentals in Chicago, IL, USA • 150 Listings
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Chicago, IL, USA Vacation Rentals | 

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United States Illinois Chicago vacation rental compare prices direct by owner 26512134
Book Direct
4.8 (4)
4BD Condo w/Parking & Game Room
Up to 10 guests
EstimatedVerified Host$400
Vrbo$400
Airbnb
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 37850709
Book Direct
5.0 (3)
Chic Studio in Prime location| Walk to Train& Bus
Up to 2 guests
Verified Host
Airbnb
United States Illinois Chicago vacation rental compare prices direct by owner 36745984
Book Direct
4.8 (22)
Renovated 2 BR in Prime Location| Pet Friendly
Up to 4 guests
Verified Host
Airbnb
United States Illinois Chicago vacation rental compare prices direct by owner 37850712
Book Direct
4.8 (4)
Spacious Studio with Balcony| Near Blue Line
Up to 3 guests
Verified Host
Airbnb
United States Illinois Chicago vacation rental compare prices direct by owner 37850727
Book Direct
4.5 (14)
Chic Studio Unit | Walk to Train& Bus
Up to 2 guests
Verified Host
Airbnb
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United States Illinois Chicago vacation rental compare prices direct by owner 12050923
Property Manager
5.0 (1)
Lovely West Loop 1BR w/ Gym & Pool in heart of Greektown, by Blueground
Up to 2 guests
Vrbo$172
Property Manager
Airbnb
Booking.com
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 29060247
5.0 (2)
Stylish 2BR Apartment with Optional Parking, Patio and Gym Near McCormick Pla...
Up to 6 guests
Booking.com$127
Vrbo$319
Airbnb
Average Nightly Rate

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United States Indiana Chesterton vacation rental compare prices direct by owner 11383937
5.0 (71)
Your Midwest Dunes Vacation Tri-State Paradise!
Up to 6 guests
Vrbo$137
Booking.com
Airbnb
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 485720
4.9 (109)
The Avondale Attic Unit
Up to 2 guests
Vrbo$78
Airbnb
Booking.com
Average Nightly Rate

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United States Illinois Chicago vacation rental compare prices direct by owner 2112541
4.9 (148)
Level ◆ Two Bedroom Deluxe Corner Suite + Balcony
Up to 6 guests
Vrbo$473
Airbnb
Booking.com
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 457137
4.8 (236)
Luxe 3BD/2BA with Fireplace and Private Balcony
Up to 6 guests
Booking.com$243
Vrbo$587
Airbnb
Average Nightly Rate
United States Chicago vacation rental compare prices direct by owner 29696988
4.8 (2)
McCormick Place Spacious 5BR Suite with Pool Table & Optional Parking Sleeps ...
Up to 10 guests
Booking.com$204
Airbnb
Vrbo
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 32509468
4.7 (90)
Chic 2BR Avondale Apt next to Logan Sq & Blue Line
Up to 4 guests
Booking.com$62
Vrbo$314
Airbnb
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 26510573
4.7 (84)
McCormick Place Magnificent 2BR with Optional Parking, Patio, Gym Access Near...
Up to 6 guests
Booking.com$64
Vrbo$350
Airbnb
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 27328298
4.7 (24)
2 New Construction Suites Same Place
Up to 16 guests
Vrbo$547
Booking.com
Airbnb
Average Nightly Rate
United States Chicago vacation rental compare prices direct by owner 36639711
4.7 (10)
Foundry Unmatched Skyline Views at Lincoln Park
Up to 4 guests
Booking.com$369
Airbnb
Vrbo
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 4631035
4.6 (125)
Kasa River North Chicago
Up to 5 guests
Booking.com$112
Vrbo$338
Airbnb
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 1793296
4.5 (678)
Kasa Magnificent Mile Chicago
Up to 3 guests
Vrbo$359
Booking.com$361
Airbnb
Average Nightly Rate
United States Des Plaines vacation rental compare prices direct by owner 13232924
4.5 (19)
Lg. 2 br Apt. North of Chicago w/ Free Parking
Up to 6 guests
Booking.com
Airbnb
Vrbo
United States Illinois Chicago vacation rental compare prices direct by owner 25570958
4.5 (15)
Charming 3BR Chicago Apt in Prime Location
Up to 6 guests
Booking.com$59
Vrbo$363
Airbnb
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 28635563
4.5 (2)
McCormick Place 2BR Oasis with Optional Parking, Patio, Gym for up to 6 guest...
Up to 6 guests
Booking.com$119
Vrbo$285
Airbnb
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 32748475
4.5 (1)
Level River North Two Bedroom Junior Suite
Up to 4 guests
Vrbo$369
Airbnb
Booking.com
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 36386275
4.5 (13)
Beautiful Unit CHI in Prime River North - 1
Up to 8 guests
Vrbo$492
Airbnb
Booking.com
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 26545818
4.5 (34)
Breathtaking Downtown Penthouse B - Sleeps 11
Up to 11 guests
Vrbo$635
Booking.com
Airbnb
Average Nightly Rate
United States Illinois Chicago vacation rental compare prices direct by owner 6725039
4.5 (105)
Kasa River North Chicago
Up to 2 guests
Booking.com$112
Vrbo$260
Airbnb
Average Nightly Rate
  1. United States
  2. Illinois
  3. Chicago Vacation Rental Price Comparison

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