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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$159 Chicago, Illinois Special deal: 3-Star Comfort Suites Michigan Avenue Fr $159+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$93 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $93+/Nt
Save with Expedia, $16/night less
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$129 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $129+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$113 Chicago, Illinois The Palmer House Hilton in Oct: $113 & Up
Expedia
$143 Chicago, Illinois La Quinta Inn & Suites Chicago Downtown in Oct: $143 & Up
Expedia
$173 Chicago, Illinois Residence Inn Chicago Downtown in Oct: $173 & Up
Expedia
$385 Chicago, Illinois Book 5-Star Four Seasons Chicago in Chicago Fr $385+/Nt
Expedia
$114 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $114+/Nt
Expedia
$133 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $133+/Nt
Expedia
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts at PUBLIC Chicago Fr $127+/Nt
Save with Expedia, $68/night less
$109 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $109+/Nt
Expedia
$144 Chicago, Illinois Chicago Savings! Book at The Silversmith Fr $144+/Nt
Save with Expedia, $25/night less
$167 Chicago, Illinois Book in Chicago: Save at the The James Chicago in Oct Fr $167+/Nt
Save with Expedia, $29/night less
$152 Chicago, Illinois Oct deal: Embassy Suites Chicago Downtown Fr $152+/Nt
Expedia
$183 Chicago, Illinois $183 & Up: Buckingham Athletic Club 3.5-Star Hotel in Chicago
Expedia
$127 Chicago, Illinois Book 3.5-Star Wyndham Grand Chicago Riverfront Fr $127+/Nt
Save with Expedia, $22/night less
$112 Chicago, Illinois Small budget: Book Radisson Blu Aqua 3 Nts in Oct Fr $112+/Nt
Expedia
$192 Chicago, Illinois Book 4.5-Star Omni Chicago Fr $192+/Nt
Save with Expedia, $47/night less
$161 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $161+/Nt
Save with Expedia, $69/night less
$116 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $116+/Nt
Expedia
$140 Chicago, Illinois Residence Inn Chicago Downtown / River North in Oct: $140 & Up
Expedia
$203 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $203+/Nt
Expedia
$166 Chicago, Illinois Book in Chicago: Save this Oct Fr $166+/Nt
Expedia
$103 Chicago, Illinois Hostelling International Chicago in Oct: $103 & Up
Expedia
$136 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Oct: $136 & Up
Expedia
$115 Chicago, Illinois theWit - A DoubleTree by Hilton in Oct: $115 & Up
Expedia
$260 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $260+/Nt
Expedia
$88 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $88+/Nt
Expedia
$171 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $171+/Nt
Expedia
$136 Chicago, Illinois Save Big This Oct! Book 3 Nts at Kinzie Fr $136+/Nt
Expedia
$119 Chicago, Illinois $119 & Up: W Chicago Lakeshore 4-Star Hotel in Chicago
Expedia
$96 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $96+/Nt
Expedia
$159 Chicago, Illinois Chicago Savings! Book at The Drake Fr $159+/Nt
Expedia
$129 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $129+/Nt
Expedia
$99 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $99+/Nt
Expedia
$159 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $159+/Nt
Expedia
$136 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $136+/Nt
Save with Expedia, $23/night less
$106 Chicago, Illinois Oct deal: Crowne Plaza Chicago Magnificent Mile Fr $106+/Nt
Expedia
$127 Chicago, Illinois Book in Chicago: Save this Oct Fr $127+/Nt
Expedia
$150 Chicago, Illinois Oct deal: Fairmont Chicago Millennium Park Fr $150+/Nt
Save with Expedia, $16/night less
$99 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $99+/Nt
Expedia
$96 Chicago, Illinois Book the The Whitehall 3 Nts in Oct Fr $96+/Nt
Save with Expedia, $23/night less
$159 Chicago, Illinois Book in Chicago: Save this Oct Fr $159+/Nt
Expedia
$169 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $169+/Nt
Expedia
$109 Chicago, Illinois Sheraton Chicago and Towers in Oct: $109 & Up
Expedia
$93 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $93+/Nt
Expedia
$115 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $115+/Nt
Expedia
$94 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $94+/Nt
Expedia
$203 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $203+/Nt
Expedia
$292 Chicago, Illinois Trump International & Tower Chicago in Oct: $292 & Up
Save with Expedia, $73/night less
$126 Chicago, Illinois Book 3-Star Congress Plaza in Chicago Fr $126+/Nt
Expedia
$198 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $198+/Nt
Expedia
$119 Chicago, Illinois Special deal: 4-Star Palomar Chicago, a Kimpton Fr $119+/Nt
Save with Expedia, $20/night less
$370 Chicago, Illinois The Peninsula Chicago in Oct: $370 & Up
Save with Expedia, $185/night less
$84 Chicago, Illinois Book 3.5-Star River Fr $84+/Nt
Save with Expedia, $9/night less
$123 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $123+/Nt
Expedia
$127 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $127+/Nt
Expedia
$116 Chicago, Illinois Oct deal: Chicago Marriott at Medical District/UIC Fr $116+/Nt
Expedia
$328 Chicago, Illinois Book 5-Star Waldorf Astoria Chicago in Chicago Fr $328+/Nt
Expedia
$115 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $115+/Nt
Expedia
$94 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $94+/Nt
Save with Expedia, $23/night less
$104 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $104+/Nt
Save with Expedia, $25/night less
$121 Chicago, Illinois Oct deal: The Westin Michigan Avenue Chicago Fr $121+/Nt
Expedia
$133 Chicago, Illinois $133 & Up: Warwick Allerton Chicago 4-Star Hotel in Chicago
Save with Expedia, $90/night less
$96 Chicago, Illinois Book in Chicago: Save at the Central Loop in Oct Fr $96+/Nt
Expedia
$124 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $124+/Nt
Expedia
$133 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $133+/Nt
Save with Expedia, $6/night less
$197 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $197+/Nt
Expedia
$129 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $129+/Nt
Expedia
$153 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $153+/Nt
Expedia
$159 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $159+/Nt
Expedia
$149 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $149+/Nt
Expedia
$163 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $163+/Nt
Expedia
$179 Chicago, Illinois Book 3.5-Star Hyatt Regency McCormick Place Fr $179+/Nt
Expedia
$88 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Oct: $88 & Up
Save with Expedia, $22/night less
$149 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $149+/Nt
Expedia
$168 Chicago, Illinois Chicago Savings! Book at Swissotel Chicago Fr $168+/Nt
Save with Expedia, $42/night less
$69 Chicago, Illinois Book 3-Star The Tremont Chicago at Magnificent Mile Fr $69+/Nt
Expedia
$103 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $103+/Nt
Expedia
$336 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Oct: $336 & Up
Save with Expedia, $60/night less
$135 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $135+/Nt
Save with Expedia, $44/night less
$139 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $139+/Nt
Expedia
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts at Burnham - a Kimpton Fr $127+/Nt
Save with Expedia, $22/night less
$102 Chicago, Illinois Special deal: 4-Star Millennium Knickerbocker Chicago Fr $102+/Nt
Save with Expedia, $17/night less
$111 Chicago, Illinois Book 3-Star Holiday Inn Chicago Downtown Fr $111+/Nt
Expedia
$136 Chicago, Illinois Oct deal: Chicago Marriott Downtown Magnificent Mile Fr $136+/Nt
Expedia
$116 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $116+/Nt
Save with Expedia, $21/night less
$133 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $133+/Nt
Save with Expedia, $71/night less
$188 Chicago, Illinois Book the The Blackstone A Renaissance 3 Nts in Oct Fr $188+/Nt
Expedia
$99 Skokie, Illinois Skokie Savings! Book 3 Nts in Oct Fr $99+/Nt
Expedia
$79 Oakbrook Terrace, Illinois Book 3-Star Hilton Garden Inn Oakbrook Terrace Fr $79+/Nt
Expedia
$114 Willowbrook, Illinois Book 3.5-Star Champagne Lodge and Luxury Suites Fr $114+/Nt
Save with Expedia, $31/night less
$92 Schiller Park, Illinois Save Big This Oct! Book 3 Nts in Schiller Park Fr $92+/Nt
Expedia
$103 Addison, Illinois Addison Savings! Book at Hampton Inn & Suites Addison Fr $103+/Nt
Expedia
$93 Rosemont, Illinois Book in Rosemont: Save this Oct Fr $93+/Nt
Expedia
$117 Addison, Illinois Save Big This Oct! Book 3 Nts in Addison Fr $117+/Nt
Expedia
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$260 New York City, New York American Airlines Domestic Getaways for This Weekend - 10/24/14
DealBase.com
$212 New York City, New York Cheap Flights from Raleigh
DealBase.com
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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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