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Search results; Over 1,000 homes in Chicago

Superhost
Hotel room in Chicago
Sun-Filled King Room in Boutique Wicker Park B&B
1 bedroom, 1 bed, 2 private bathrooms
29 Aug – 3 Sept
,
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.93 out of 5 average rating, 27 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Dec
4.95 out of 5 average rating, 126 reviews
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
New place to stay
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
4–9 Aug
4.94 out of 5 average rating, 108 reviews
Flat in Chicago
Gym + Workspace • Sleeps 8 • Near O’Hare
3 bedrooms, 3 queen beds, 2 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
1 queen bed, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 525 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
New place to stay
Top guest favourite
Flat in Chicago
Best City Views • Rooftop Nights • EV Garage Free
2 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
4.98 out of 5 average rating, 88 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds, 3 bathrooms
11–16 Aug
5.0 out of 5 average rating, 21 reviews
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bed, 1 bathroom
9–14 Aug
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
26–31 Dec
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 252 reviews
Top guest favourite
Flat in Chicago
Cozy & Spacious Sunny 2 bedroom apartment.
2 bedrooms, 2 beds, 1 bathroom
19–24 Oct
4.98 out of 5 average rating, 108 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
4.96 out of 5 average rating, 305 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 68 reviews
Top guest favourite
Flat in Forest Park
Walk to Oak Park from this Newly Remodeled Gem
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 274 reviews