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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$141 Chicago, Illinois $141 & Up: Blake Chicago 3.5-Star Hotel in Chicago
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$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
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$190 Chicago, Illinois $190 & Up: Hyatt Chicago Magnificent Mile 4-Star Hotel in Chicago
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$375 Chicago, Illinois $375 & Up: Waldorf Astoria Chicago 5-Star Hotel in Chicago
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$110 Chicago, Illinois Book 3 Nts in Chicago this May Fr $110+/Nt
Save with Expedia, $19/night less
$168 Chicago, Illinois Book 3 Nts in Chicago this May Fr $168+/Nt
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$239 Chicago, Illinois Book 3 Nts in Chicago this May Fr $239+/Nt
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$98 Chicago, Illinois Book 3 Nts in Chicago this May Fr $98+/Nt
Save with Expedia, $32/night less
$159 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $159+/Nt
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$103 Chicago, Illinois Book 3-Star Holiday Inn Express Cass in Chicago Fr $103+/Nt
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$139 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $139+/Nt
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$121 Chicago, Illinois Book 3.5-Star River Fr $121+/Nt
Save with Expedia, $15/night less
$189 Chicago, Illinois Book 4-Star PUBLIC Chicago Fr $189+/Nt
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$224 Chicago, Illinois Book 4-Star The Westin Chicago River North in Chicago Fr $224+/Nt
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$189 Chicago, Illinois Book 4-Star theWit - A DoubleTree by Hilton Fr $189+/Nt
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$172 Chicago, Illinois Book 4-Star W Chicago - City Center in Chicago Fr $172+/Nt
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$176 Chicago, Illinois Book 4-Star W Chicago Lakeshore in Chicago Fr $176+/Nt
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$138 Chicago, Illinois Book in Chicago: Save this May Fr $138+/Nt
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$176 Chicago, Illinois Book in Chicago: Save this May Fr $176+/Nt
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$186 Chicago, Illinois Book in Chicago: Save this May Fr $186+/Nt
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$127 Chicago, Illinois Book the Hard Rock Chicago 3 Nts in May Fr $127+/Nt
Save with Expedia, $42/night less
$84 Chicago, Illinois Book the Hostelling International Chicago 3 Nts in May Fr $84+/Nt
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$126 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $126+/Nt
Save with Expedia, $13/night less
$144 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $144+/Nt
Save with Expedia, $25/night less
$144 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $144+/Nt
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$184 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $184+/Nt
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$192 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $192+/Nt
Save with Expedia, $47/night less
$195 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $195+/Nt
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$196 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $196+/Nt
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$159 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $159+/Nt
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$193 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $193+/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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$246 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $246+/Nt
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$190 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $190+/Nt
Save with Expedia, $9/night less
$221 Chicago, Illinois Chicago Savings! Book at Radisson Blu Aqua Fr $221+/Nt
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$219 Chicago, Illinois Chicago Savings! Book at Rush Fr $219+/Nt
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$237 Chicago, Illinois Chicago Savings! Book at Swissotel Chicago Fr $237+/Nt
Save with Expedia, $26/night less
$165 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $165+/Nt
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$176 Chicago, Illinois Felix in May: $176 & Up
Save with Expedia, $31/night less
$169 Chicago, Illinois Hampton Inn Chicago Downtown/Magnificent Mile in May: $169 & Up
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$176 Chicago, Illinois Kinzie in May: $176 & Up
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$141 Chicago, Illinois May deal: Chicago Downtown, Autograph Collection Fr $141+/Nt
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$251 Chicago, Illinois May deal: Chicago Marriott at Medical District/UIC Fr $251+/Nt
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$206 Chicago, Illinois May deal: Chicago Marriott Downtown Magnificent Mile Fr $206+/Nt
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$175 Chicago, Illinois May deal: Crowne Plaza Chicago - The Metro Fr $175+/Nt
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$209 Chicago, Illinois May deal: Hampton Majestic Chicago Theatre District Fr $209+/Nt
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$142 Chicago, Illinois May deal: Homewood Suites by Hilton Chicago Downtown Fr $142+/Nt
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$237 Chicago, Illinois May deal: Renaissance Chicago Fr $237+/Nt
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$192 Chicago, Illinois May deal: Sofitel Chicago Water Tower Fr $192+/Nt
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$208 Chicago, Illinois May deal: The Westin Michigan Avenue Chicago Fr $208+/Nt
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$159 Chicago, Illinois Save at 4-Star Allegro Chicago - a Kimpton: $159 & Up in May
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$166 Chicago, Illinois Save at 4-Star Hilton Chicago O'Hare Airport: $166 & Up in May
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$169 Chicago, Illinois Save at 4-Star Hyatt Regency Chicago: $169 & Up in May
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$304 Chicago, Illinois Save at 5-Star Four Seasons Chicago: $304 & Up in May
Save with Expedia, $151/night less
$183 Chicago, Illinois Save Big This May! Book 3 Nts at MileNorth, A Chicago Fr $183+/Nt
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$145 Chicago, Illinois Save Big This May! Book 3 Nts at The Whitehall Fr $145+/Nt
Save with Expedia, $8/night less
$126 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $126+/Nt
Save with Expedia, $22/night less
$126 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $126+/Nt
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$166 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $166+/Nt
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$180 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $180+/Nt
Save with Expedia, $20/night less
$180 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $180+/Nt
Save with Expedia, $19/night less
$199 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $199+/Nt
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$209 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $209+/Nt
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$218 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $218+/Nt
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$239 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $239+/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
$143 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $143+/Nt
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$153 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $153+/Nt
Save with Expedia, $26/night less
$156 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $156+/Nt
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$200 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $200+/Nt
Save with Expedia, $86/night less
$201 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $201+/Nt
Save with Expedia, $35/night less
$203 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $203+/Nt
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$190 Chicago, Illinois Small budget: Stay in Chicago this May Fr $190+/Nt
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$194 Chicago, Illinois Small budget: Stay in Chicago this May Fr $194+/Nt
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$199 Chicago, Illinois Small budget: Stay in Chicago this May Fr $199+/Nt
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$139 Chicago, Illinois Special deal: 3-Star Comfort Suites Michigan Avenue Fr $139+/Nt
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$159 Chicago, Illinois Special deal: 3-Star Congress Plaza Fr $159+/Nt
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$133 Chicago, Illinois Special deal: 4-Star Warwick Allerton Chicago Fr $133+/Nt
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$469 Chicago, Illinois Special deal: 5-Star The Peninsula Chicago Fr $469+/Nt
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$213 Chicago, Illinois The Drake on Sale: Book 3 Nts in May Fr $213+/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
$153 Chicago, Illinois Wyndham Grand Chicago Riverfront in May: $153 & Up
Save with Expedia, $16/night less
$35+ Oak Park, Illinois Oak Park Vacation Rental Deals From $35
Tripping
$96 Addison, Illinois Addison Savings! Book at Hampton Inn & Suites Addison Fr $96+/Nt
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$43+ Downers Grove, Illinois Downers Grove Vacation Rental Deals From $43
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$134 Rosemont, Illinois BEST WESTERN at O'Hare in May: $134 & Up
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$59+ Elmhurst, Illinois Elmhurst Vacation Rental Deals From $59
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$96 Burbank, Illinois BEST WESTERN Inn & Suites - Midway Airport in May: $96 & Up
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$50+ Evanston, Illinois Evanston Vacation Rental Deals From $50
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$109 Arlington Heights, Illinois Book 3 Nts in Arlington Heights this May Fr $109+/Nt
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$119 Deerfield, Illinois Book 3 Nts in Deerfield this May Fr $119+/Nt
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$149 Oak Brook, Illinois Book 3 Nts in Oak Brook this May Fr $149+/Nt
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$119 Rosemont, Illinois Book 3 Nts in Rosemont this May Fr $119+/Nt
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$117 Tinley Park, Illinois Book 3 Nts in Tinley Park this May Fr $117+/Nt
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$104 Wood Dale, Illinois Book 3 Nts in Wood Dale this May Fr $104+/Nt
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$170 Bedford Park, Illinois Book 3-Star Hilton Garden Inn Chicago Midway Airport Fr $170+/Nt
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$98 Lombard, Illinois Book 3-Star Hyatt Place Chicago/Lombard Fr $98+/Nt
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$121 Willowbrook, Illinois Book 3.5-Star Champagne Lodge and Luxury Suites Fr $121+/Nt
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$126 Oakbrook Terrace, Illinois Book 3.5-Star Hilton Chicago Oak Brook Suites Fr $126+/Nt
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PRICEDESTINATIONDEAL
$53 Philadelphia, Pennsylvania Spirit Airlines Senioritis Deals
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$187 Philadelphia, Pennsylvania Cheap Flights from Las Vegas
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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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