Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Estates
Hotels
Homes
Boats
Studios
Townhomes
Villas
Barns
Bungalows
Cabins
Castles
Chalets
Cottages
Farmhouses
Lodges
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Welcome to the new VacationRentals.com! Use the new filters and search options to find your next vacation rental.

Chicago Vacation Rentals(132)

132 Results
3 - 5 night minimum stay
(103)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(7)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
4 night minimum stay
(42)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
Special Offer! 25% off all stays from November 7th-December 22nd!!! November 7 - December 22
2 - 3 night minimum stay
(14)
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 24
Special Offer! Midweek DEAL!- $300/nt. M,T,W nights in Oct, Nov, Dec. October 9 - December 20
2 night minimum stay
(4)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 4 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 8
Special Offer! $125/n November Special November 1 - November 30
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 14
2 - 3 night minimum stay
(128)
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(29)
  • 5 BR,
  • 3 BA,
  • Sleeps 13
3 - 5 night minimum stay
(6)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
27 - 30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
Special Offer! $199/n November Special November 5 - November 29
1 Review
  • 2 BR,
  • 1 BA,
  • Sleeps 6
4 night minimum stay
(28)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
  • 1 BR,
  • 1 BA,
  • Sleeps 4
30 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
4 night minimum stay
(27)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
3 - 4 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
  • 3 BR,
  • 2 BA,
  • Sleeps 8
Special Offer! Fall into Savings! $30 off per night! October 13 - November 22
Special Offer! Save $30 and Live Like A Local! October 13 - November 22
2 - 4 night minimum stay
(24)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
30 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
Advertisement