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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$217 Chicago, Illinois Book 4-Star Swissotel Chicago Fr $217+/Nt
Save with Expedia, $33/night less
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$141 Chicago, Illinois $141 & Up: Blake Chicago 3.5-Star Hotel in Chicago
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$226 Chicago, Illinois Small budget: Stay in Chicago this May Fr $226+/Nt
Save with Expedia, $40/night less
$469 Chicago, Illinois Special deal: 5-Star The Peninsula Chicago Fr $469+/Nt
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$142 Chicago, Illinois Small budget: Book The Silversmith 3 Nts in May Fr $142+/Nt
Save with Expedia, $47/night less
$184 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $184+/Nt
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$234 Chicago, Illinois $234 & Up: Renaissance Chicago 3.5-Star Hotel in Chicago
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$123 Chicago, Illinois Save at 4-Star Felix: $123 & Up in May
Save with Expedia, $21/night less
$154 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $154+/Nt
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$98 Chicago, Illinois Book 3 Nts in Chicago this May Fr $98+/Nt
Save with Expedia, $32/night less
$173 Chicago, Illinois Book 3-Star La Quinta Inn & Suites Chicago Downtown Fr $173+/Nt
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$189 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $189+/Nt
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$259 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $259+/Nt
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$217 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $217+/Nt
Save with Expedia, $92/night less
$215 Chicago, Illinois May deal: Chicago Marriott Downtown Magnificent Mile Fr $215+/Nt
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$199 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $199+/Nt
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$159 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $159+/Nt
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$93 Chicago, Illinois Save in Chicago: Book 3 Nts in May at Central Loop Fr $93+/Nt
Save with Expedia, $23/night less
$189 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $189+/Nt
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$179 Chicago, Illinois May deal: Courtyard Chicago Downtown River North Fr $179+/Nt
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$153 Chicago, Illinois Book 3 Nts in Chicago this May Fr $153+/Nt
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$173 Chicago, Illinois $173 & Up: Hilton Chicago O'Hare Airport 4-Star Hotel in Chicago
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$136 Chicago, Illinois Small budget: Stay in Chicago this May Fr $136+/Nt
Save with Expedia, $23/night less
$140 Chicago, Illinois Book 3 Nts in Chicago this May Fr $140+/Nt
Save with Expedia, $23/night less
$208 Chicago, Illinois May deal: The Westin Michigan Avenue Chicago Fr $208+/Nt
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$276 Chicago, Illinois May deal: W Chicago - City Center Fr $276+/Nt
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$210 Chicago, Illinois Special deal: 4-Star Monaco Chicago - a Kimpton Fr $210+/Nt
Save with Expedia, $19/night less
$219 Chicago, Illinois Chicago Savings! Book at Rush Fr $219+/Nt
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$215 Chicago, Illinois Special deal: 4-Star The Westin Chicago River North Fr $215+/Nt
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$178 Chicago, Illinois Book 4-Star Sheraton Chicago and Towers in Chicago Fr $178+/Nt
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$125 Chicago, Illinois Save at 4-Star Millennium Knickerbocker Chicago: $125 & Up in May
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$149 Chicago, Illinois Hampton Inn & Suites Chicago - Downtown in May: $149 & Up
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$255 Chicago, Illinois Book 3 Nts in Chicago this May Fr $255+/Nt
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$142 Chicago, Illinois Save at 4-Star Hard Rock Chicago: $142 & Up in May
Save with Expedia, $47/night less
$196 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $196+/Nt
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$143 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $143+/Nt
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$218 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $218+/Nt
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$132 Chicago, Illinois Book 3.5-Star Club Quarters, Central Loop in Chicago Fr $132+/Nt
Save with Expedia, $14/night less
$169 Chicago, Illinois Hampton Inn Chicago Downtown/Magnificent Mile in May: $169 & Up
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$199 Chicago, Illinois Special deal: 4-Star Burnham - a Kimpton Fr $199+/Nt
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$168 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $168+/Nt
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$239 Chicago, Illinois Book 3 Nts in Chicago this May Fr $239+/Nt
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$116 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $116+/Nt
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$144 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $144+/Nt
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$149 Chicago, Illinois Book 3-Star Congress Plaza Fr $149+/Nt
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$151 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $151+/Nt
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$192 Chicago, Illinois May deal: Sofitel Chicago Water Tower Fr $192+/Nt
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$169 Chicago, Illinois Small budget: Stay in Chicago this May Fr $169+/Nt
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$209 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $209+/Nt
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$316 Chicago, Illinois Small budget: Book JW Marriott Chicago 3 Nts in May Fr $316+/Nt
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$152 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $152+/Nt
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$199 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $199+/Nt
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$142 Chicago, Illinois Book the Hyatt Chicago Magnificent Mile 3 Nts in May Fr $142+/Nt
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$135 Chicago, Illinois Indigo Chicago Downtown Gold Coast in May: $135 & Up
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$141 Chicago, Illinois May deal: Chicago Downtown, Autograph Collection Fr $141+/Nt
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$149 Chicago, Illinois Book in Chicago: Save this May Fr $149+/Nt
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$189 Chicago, Illinois Book 4-Star theWit - A DoubleTree by Hilton Fr $189+/Nt
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$136 Chicago, Illinois Special deal: 3-Star Holiday Inn Express Cass Fr $136+/Nt
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$196 Chicago, Illinois Book the Residence Inn Chicago Downtown 3 Nts in May Fr $196+/Nt
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$109 Chicago, Illinois Save at 3.5-Star River: $109 & Up in May
Save with Expedia, $27/night less
$144 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $144+/Nt
Save with Expedia, $25/night less
$169 Chicago, Illinois Book 3 Nts in Chicago this May Fr $169+/Nt
Expedia
$192 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $192+/Nt
Save with Expedia, $47/night less
$395 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $395+/Nt
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$248 Chicago, Illinois May deal: Chicago Marriott at Medical District/UIC Fr $248+/Nt
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$179 Chicago, Illinois Small budget: Stay in Chicago this May Fr $179+/Nt
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$183 Chicago, Illinois Save Big This May! Book 3 Nts at MileNorth, A Chicago Fr $183+/Nt
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$173 Chicago, Illinois $173 & Up: Hilton Chicago 4-Star Hotel in Chicago
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$190 Chicago, Illinois Small budget: Stay in Chicago this May Fr $190+/Nt
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$163 Chicago, Illinois May deal: W Chicago Lakeshore Fr $163+/Nt
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$175 Chicago, Illinois May deal: Crowne Plaza Chicago - The Metro Fr $175+/Nt
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$153 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $153+/Nt
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$216 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $216+/Nt
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$169 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $169+/Nt
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$290 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in May: $290 & Up
Save with Expedia, $145/night less
$187 Chicago, Illinois Book 4-Star Fairmont Chicago Millennium Park Fr $187+/Nt
Save with Expedia, $32/night less
$199 Chicago, Illinois Small budget: Stay in Chicago this May Fr $199+/Nt
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$84 Chicago, Illinois Book the Hostelling International Chicago 3 Nts in May Fr $84+/Nt
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$129 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $129+/Nt
Save with Expedia, $22/night less
$180 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $180+/Nt
Save with Expedia, $20/night less
$169 Chicago, Illinois Save at 4-Star Hyatt Regency Chicago: $169 & Up in May
Expedia
$304 Chicago, Illinois Save at 5-Star Four Seasons Chicago: $304 & Up in May
Save with Expedia, $151/night less
$35+ Oak Park, Illinois Oak Park Vacation Rental Deals From $35
Tripping
$120 Addison, Illinois Save Big This May! Book 3 Nts in Addison Fr $120+/Nt
Expedia
$43+ Downers Grove, Illinois Downers Grove Vacation Rental Deals From $43
Tripping
$87 Addison, Illinois Book the Hampton Inn & Suites Addison 3 Nts in May Fr $87+/Nt
Expedia
$59+ Elmhurst, Illinois Elmhurst Vacation Rental Deals From $59
Tripping
$143 Alsip, Illinois Save in Alsip: Book 3 Nts in May Fr $143+/Nt
Expedia
$50+ Evanston, Illinois Evanston Vacation Rental Deals From $50
Tripping
$110 Arlington Heights, Illinois Save Big This May! Book 3 Nts in Arlington Heights Fr $110+/Nt
Expedia
$136 Bedford Park, Illinois May deal: Hampton Inn Chicago-Midway Airport Fr $136+/Nt
Expedia
$170 Bedford Park, Illinois Book 3-Star Hilton Garden Inn Chicago Midway Airport Fr $170+/Nt
Expedia
$93 Bensenville, Illinois Save Big This May! Book 3 Nts in Bensenville Fr $93+/Nt
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$117 Bloomingdale, Illinois Save in Bloomingdale: Book 3 Nts in May Fr $117+/Nt
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$145 Bolingbrook, Illinois Small budget: Book aloft Bolingbrook 3 Nts in May Fr $145+/Nt
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$68 Bridgeview, Illinois Small budget: Stay in Bridgeview this May Fr $68+/Nt
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$94 Burbank, Illinois May deal: BEST WESTERN Inn & Suites - Midway Airport Fr $94+/Nt
Expedia
$96 Carol Stream, Illinois Hampton Inn Chicago-Carol Stream in May: $96 & Up
Expedia
$96 Countryside, Illinois Save in Countryside: Book 3 Nts in May Fr $96+/Nt
Expedia
PRICEDESTINATIONDEAL
$137 Philadelphia, Pennsylvania Cheap Flights from Chicago
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$389 Philadelphia, Pennsylvania Cheap Flights from Los Angeles
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$177 Philadelphia, Pennsylvania Cheap Flights from Dallas
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Chicago Travel Tips

A shiny metropolis where complete strangers ask you if you need directions? Only in the Midwest. Take in loads of friendliness, not to mention cool architecture and major museums.
  • It's a great view … if you're a girl. One of the best views of the city is from the ladies' room in the Hancock Building's Signature Lounge. Tough luck, gentlemen.
  • You can make your mark, just don't use profanity. Gino's East Pizza bakes pies-to-die-for and features patron-placed graffiti all over its walls and tables.
  • Fond o' fondue, are you? Us too. Visit Geja's Cafe in Lincoln Park, a romantically-lit grotto with an astounding array of dip-able dining that also features flamenco and classical guitarists.
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