Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Chicago Long Term Vacation Rentals(137)

137 Results
$625 - $1,253
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(110)
$260 - $450
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(185)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(47)
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
2 - 4 night minimum stay
(56)
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
3 - 4 night minimum stay
(31)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 8
3 - 5 night minimum stay
(47)
$199 - $269
per night
2 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 5 night minimum stay
(26)
$550 - $1,110
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
3 - 5 night minimum stay
(32)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 3 night minimum stay
(32)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 - 3 night minimum stay
(25)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
1 - 3 night minimum stay
(29)
  • 4 BR,
  • 2 BA,
  • Sleeps 9
1 - 3 night minimum stay
(25)
$439
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(62)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
6 night minimum stay
(11)
$159 - $199
per night
2 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(21)
$625 - $1,235
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(4)
$950 - $1,350
per night
2 - 3 night minimum stay
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 24
2 - 3 night minimum stay
(14)
$135 - $299
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 5 night minimum stay
(3)
$80 - $179
per night
3 - 4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 - 4 night minimum stay
$219 - $299
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 7
2 - 3 night minimum stay
(128)
$799 - $899
per night
2 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
2 Reviews
  • 2 BR,
  • 1 BA,
  • Sleeps 22
2 - 30 night minimum stay
1 Review
$350
per night
3 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 8
3 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(17)
$159 - $349
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(12)
  • 2 BR,
  • 2 BA,
  • Sleeps 14
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(6)
Advertisement
 

Recent Chicago Reviews

DODGERS @wrigley

5 of 5
I gave the rental 5 stars because it was more than I expected. The place was less than a block from the stadium and within walking distance to the bars/ pubs and train (according to the locals it was the nicest part of the town). We traveled as a group of 8 men and were concerned about the listing at first. The listing states 3 bedrooms 1 bath but sleeps 8. Come to find out upon check-in that there were 3 bathrooms and 5 bedrooms and a separate futon (needless to say we all slept comfortable). The place is a great place to stay and I would definately recommend it to anyone from families to big groups of guys. We had a blast there and got to see the DODGERS beat the CUBS 3 out of 4 games. Only problem we had was not having an iron but there was a CVS a few blocks away and that fixed that. This was my first booking and I was a little worried about getting a hold of the owner they did take a little bit of time to get back to me but when they did everything worked out perfect. In his defense he did state he was on vacation at the time.
  • Submitted: Sep 25, 2014
  • Stayed: Sep 2014

Great Apartment after climbing 44 steps!

4 of 5
We had the apartment to stay at over our wedding weekend. This is a great place in a great location, near els, stores, cabs, easy to walk to Michigan Avenue and the Loop. Well-designed, with the two smaller bedrooms separated from the master, wonderful living space. Dramatic apartment! The ad should have mentioned the 44-step climb to the apartment. My 83 year old mother-in-law made it okay, but it would have been nice to know. Other suggestions: a better equipped kitchen (spatulas, non-stick pans, etc), and more water pressure in the master bath shower. And - -- please have blinds put on the double doors to the master bedroom! The eastern sun comes streaming in early in the morning, and on the day after the wedding, we didn't need that! But - - - still a great apartment! And good hosts!
  • Submitted: Sep 11, 2014
  • Stayed: Sep 2014

A+++

5 of 5
Labor Day get away in the city. Nothing better than Wrigleyville in the summer. Awesome to stay in a rooftop! The apartment was nice, clean & spacious.
  • Submitted: Sep 8, 2014
  • Stayed: Sep 2014