Vacation rentals in Chicago
Chicago, Illinois is a vibrant city located on the shores of Lake Michigan. Known for its iconic skyline, deep-dish pizza, and world-class museums, Chicago offers something for everyone, from sports fans to foodies to culture seekers.
Top rated hotels in Chicago
Show more
Vacation rentals with Wifi in Chicago
Show more
Budget-friendly vacation rentals in Chicago
Show more
Book a hotel in Chicago
Show more
More vacation rentals & hotels in Chicago
Show more
Chicago · 6 guests · 4 beds · 3 bathFamily-Friendly South Loop EscapeFrom $388 /night
Chicago · 9 guests · 4 beds · 2.5 bathWindy City Getaway | 3BR 2BA Chicago TownhouseFrom $180 /night
Chicago · 10 guests · 5 beds · 2 bathHeart of Wrigleyville 4bd 2ba Long Stay Modern AptFrom $195 /night
Chicago · 7 guests · 4 beds · 1 bathComfortable Condo in the Heart of BronzevilleFrom $243 /night
Chicago · 6 guests · 3 beds · 1 bathChic Chicago RetreatFrom $112 /night
Chicago · 6 guests · 3 beds · 2 bath2bd River North Million Dollar Views! Parking InclFrom $235 /night
Chicago · 2 guests · 2 beds · 1 bathCabin 105 at 747 LoftsFrom $72 /night
Chicago · 2 guests · 1 bed · 1 bathCabin 208 at 747 LoftsFrom $63 /night
Chicago · 5 guests · 4 beds · 2 bath2BR Elevator Bldg Condo - Steps to Restaurant Row!From $113 /night
Chicago · 3 guests · 2 beds · 1 bathCabin 202 at 747 LoftsFrom $73 /night
Chicago · 3 guests · 2 beds · 1 bathCabin 203 at 747 LoftsFrom $63 /night
Chicago · 4 guests · 2 beds · 1 bath2 Bedroom Apartment in West TownFrom $89 /night
Chicago · 1 guest · 1 bed · 1 bathCabin 305 at 747 LoftsFrom $58 /night
Chicago · 3 guests · 1 bed · 1 bathGreat 1 BR Apartment in West TownFrom $78 /night
Chicago · 4 guests · 3 beds · 1 bathWalk to IL Medical District 1 Bed w/Parking & W/DFrom $73 /night
Chicago · 1 guest · 1 bed · 1 bathCabin 102 at 747 LoftsFrom $56 /night
Chicago · 2 guests · 1 bed · 1 bathCabin 308 at 747 LoftsFrom $77 /night
Chicago · 2 guests · 1 bed · 1 bathCabin 104 at 747 LoftsFrom $63 /night
Chicago · 8 guests · 5 beds · 2 bathWelcoming Duplex w/ Parking next to Humboldt Park!From $153 /night
Chicago · 2 guests · 1 bed · 1 bathCabin 106 at 747 LoftsFrom $63 /night
Chicago · 3 guests · 2 beds · 1 bathCabin 301 at 747 LoftsFrom $79 /night
Chicago · 3 guests · 2 beds · 1 bathCabin 303 at 747 LoftsFrom $63 /night
Chicago · 16 guests · 11 beds · 4 bathMassive Old Town home steps to Wells St & BeachFrom $538 /night
Chicago · 1 guest · 1 bed · 1 bathCabin 207 at 747 LoftsFrom $62 /night
Chicago · 2 guests · 1 bed · 1 bathCabin 307 at 747 LoftsFrom $71 /night
Chicago · 3 guests · 2 beds · 1 bathCabin 101 at 747 LoftsFrom $72 /night
Chicago · 4 guests · 2 beds · 2 bathSpacious 2 Bed/2 Bath Apartment in West Town!From $142 /night
Chicago · 3 guests · 2 beds · 1 bathCabin 302 at 747 LoftsFrom $86 /night
Chicago · 2 guests · 1 bed · 1 bathAmazing 1 Bedroom in Prime Lakeview LocationFrom $82 /night
Chicago · 1 guest · 1 bed · 1 bathCabin 304 at 747 LoftsFrom $58 /night
Chicago · 1 guest · 1 bed · 1 bathCabin 205 at 747 LoftsFrom $63 /night
Chicago · 3 guests · 2 beds · 1 bathCabin 201 at 747 LoftsFrom $83 /night
Chicago · 7 guests · 4 beds · 2 bathLong Term Rental: 3BR/2BA River West CondoFrom $156 /night
Chicago · 3 guests · 2 beds · 1 bathCabin 306 at 747 LoftsFrom $70 /night
Chicago · 1 guest · 2 bedsThe Whitehall HotelFrom $92 /night
Chicago · 4 guests · 2 bedsHomewood Suites by Hilton Chicago-DowntownFrom $118 /night
Chicago · 4 guests · 2 bedsPalmer House a Hilton HotelFrom $143 /night
Chicago · 4 guests · 2 bedsHilton Garden Inn Chicago Downtown/Magnificent MileFrom $94 /night
Chicago · 4 guests · 2 bedsThe DrakeFrom $131 /night
Chicago · 1 guest · 1 bedHotel Versey Days Inn by Wyndham ChicagoFrom $148 /night
Chicago · 6 guests · 3 bedsEmbassy Suites by Hilton Chicago Downtown Magnificent MileFrom $134 /night
Chicago · 4 guests · 2 bedsRenaissance Chicago O'Hare Suites HotelFrom $100 /night
Chicago · 5 guests · 2 bedsHampton Inn & Suites Chicago DowntownFrom $127 /night
Chicago · 4 guests · 2 bedsCourtyard by Marriott Chicago Midway AirportFrom $135 /night
Chicago · 4 guests · 2 bedsFairfield Inn & Suites Chicago Downtown / Magnificent MileFrom $98 /night
Chicago · 4 guests · 2 bedsCarlton Inn MidwayFrom $119 /night
Chicago · 6 guests · 10 bedsChicago Getaway HostelFrom $35 /night
Chicago · 4 guests · 1 bedOmni Chicago HotelFrom $204 /night
Chicago · 4 guests · 2 bedsCrowne Plaza Chicago West Loop, an IHG HotelFrom $120 /night
Chicago · 6 guests · 2 bedsSpringHill Suites Chicago O'Hare by MarriottFrom $116 /night
Chicago · 4 guests · 2 bedsHilton ChicagoFrom $140 /night
Chicago · 5 guests · 2 bedsHilton Chicago/Magnificent Mile SuitesFrom $111 /night
Chicago · 4 guests · 2 bedsHampton Inn by Hilton Chicago-Midway AirportFrom $127 /night
Chicago · 3 guests · 1 bedThe Majestic HotelFrom $255 /night
Chicago · 3 guests · 1 bedCity Suites HotelFrom $229 /night
Chicago · 4 guests · 2 bedsThe Willows HotelFrom $159 /night
Chicago · 4 guests · 2 bedsResidence Inn Marriott Chicago MidwayFrom $144 /night
Chicago · 4 guests · 2 bedsFairfield Inn and Suites by Marriott Chicago Midway AirportFrom $118 /night
Chicago · 4 guests · 2 bedsChicago Marriott Downtown Magnificent MileFrom $195 /night
Chicago · 4 guests · 2 bedsHotel Saint Clair- Magnificent MileFrom $99 /night
Chicago · 4 guests · 2 bedsThe Buckingham HotelFrom $110 /night
Chicago · 4 guests · 2 bedsLa Quinta Inn & Suites by Wyndham Chicago DowntownFrom $113 /night
Chicago · 1 guest · 1 bedThe Villa ToscanaFrom $115 /night
Chicago · 3 guests · 1 bedIvy Boutique HotelFrom $118 /night
Chicago · 3 guests · 2 bedsCentral Loop HotelFrom $113 /night
Chicago · 2 guests · 1 bedVilla Dubois Guest HouseFrom $85 /night
Chicago · 4 guests · 2 bedsHotel Felix River North/Magnificent MileFrom $99 /night
Chicago · 2 guests · 1 bedStay 424 HostelFrom $70 /night
Chicago · 4 guests · 2 bedsInterContinental Chicago Magnificent Mile, an IHG HotelFrom $169 /night
Chicago · 4 guests · 2 bedsThe Chicago Hotel Collection - WrigleyvilleFrom $303 /night
Chicago · 4 guests · 2 bedsThe St. Regis ChicagoFrom $525 /night
Chicago · 4 guests · 2 bedsResidence Inn by Marriott Chicago Downtown / River NorthFrom $119 /night
Chicago · 4 guests · 2 bedsExtended Stay America Suites Chicago MidwayFrom $85 /night
Chicago · 4 guests · 2 bedsClaridge HouseFrom $102 /night
Chicago · 6 guests · 2 bedsFairmont Chicago at Millennium ParkFrom $170 /night
Chicago · 6 guests · 3 bedsLevel Chicago Fulton MarketFrom $148 /night
Chicago · 4 guests · 2 bedsSonder The Burnham ApartmentsFrom $134 /night
Chicago · 4 guests · 2 bedsSwissotel - ChicagoFrom $166 /night
Typical weather in Chicago
31°
18°
☂
10 days
10 days
36°
21°
☂
8 days
8 days
46°
30°
☂
11 days
11 days
59°
41°
☂
12 days
12 days
70°
51°
☂
12 days
12 days
81°
62°
☂
10 days
10 days
85°
68°
☂
9 days
9 days
83°
67°
☂
9 days
9 days
76°
58°
☂
9 days
9 days
64°
47°
☂
10 days
10 days
49°
35°
☂
11 days
11 days
36°
23°
☂
10 days
10 days
Jan.
Feb.
Mar.
Apr.
May.
Jun.
Jul.
Aug.
Sep.
Oct.
Nov.
Dec.