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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$115 Chicago, Illinois Special deal: 4-Star theWit - A DoubleTree by Hilton Fr $115+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$102 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $102+/Nt
Expedia
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$144 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $144+/Nt
Save with Expedia, $15/night less
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$85 Chicago, Illinois Save Big This Oct! Book 3 Nts at Chicago's Essex Inn Fr $85+/Nt
Save with Expedia, $14/night less
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$144 Chicago, Illinois The Silversmith on Sale: Book 3 Nts in Oct Fr $144+/Nt
Save with Expedia, $25/night less
$138 Chicago, Illinois Save Big This Oct! Book 3 Nts at Radisson Blu Aqua Fr $138+/Nt
Expedia
$143 Chicago, Illinois Book in Chicago: Save this Oct Fr $143+/Nt
Expedia
$128 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $128+/Nt
Expedia
$109 Chicago, Illinois Book in Chicago: Save this Oct Fr $109+/Nt
Expedia
$85 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $85+/Nt
Save with Expedia, $14/night less
$136 Chicago, Illinois Book in Chicago: Save this Oct Fr $136+/Nt
Expedia
$94 Chicago, Illinois Hyatt Regency Chicago in Oct: $94 & Up
Expedia
$140 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $140+/Nt
Expedia
$95 Chicago, Illinois Book 3.5-Star Embassy Suites Chicago Downtown Fr $95+/Nt
Expedia
$123 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Oct: $123 & Up
Expedia
$116 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $116+/Nt
Expedia
$156 Chicago, Illinois Book the Sofitel Chicago Water Tower 3 Nts in Oct Fr $156+/Nt
Expedia
$85 Chicago, Illinois Book in Chicago: Save this Oct Fr $85+/Nt
Expedia
$153 Chicago, Illinois Book the W Chicago - City Center 3 Nts in Oct Fr $153+/Nt
Expedia
$129 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $129+/Nt
Expedia
$199 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $199+/Nt
Expedia
$188 Chicago, Illinois Book in Chicago: Save this Oct Fr $188+/Nt
Expedia
$297 Chicago, Illinois Trump International & Tower Chicago in Oct: $297 & Up
Save with Expedia, $98/night less
$147 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $147+/Nt
Save with Expedia, $26/night less
$126 Chicago, Illinois Book in Chicago: Save at the Congress Plaza in Oct Fr $126+/Nt
Expedia
$139 Chicago, Illinois Residence Inn Chicago Downtown in Oct: $139 & Up
Expedia
$110 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $110+/Nt
Expedia
$91 Chicago, Illinois Book 3.5-Star Blake Chicago Fr $91+/Nt
Save with Expedia, $18/night less
$108 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $108+/Nt
Save with Expedia, $58/night less
$81 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $81+/Nt
Save with Expedia, $8/night less
$138 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $138+/Nt
Save with Expedia, $65/night less
$108 Chicago, Illinois Book in Chicago: Save this Oct Fr $108+/Nt
Save with Expedia, $57/night less
$120 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $120+/Nt
Expedia
$129 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $129+/Nt
Expedia
$159 Chicago, Illinois Oct deal: The Drake Fr $159+/Nt
Expedia
$167 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $167+/Nt
Save with Expedia, $29/night less
$166 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $166+/Nt
Expedia
$127 Chicago, Illinois Book 3.5-Star Wyndham Grand Chicago Riverfront Fr $127+/Nt
Save with Expedia, $22/night less
$183 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $183+/Nt
Expedia
$236 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $236+/Nt
Expedia
$88 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Oct: $88 & Up
Save with Expedia, $22/night less
$164 Chicago, Illinois Residence Inn Chicago Downtown / River North in Oct: $164 & Up
Expedia
$85 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $85+/Nt
Expedia
$299 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $299+/Nt
Expedia
$130 Chicago, Illinois Save Big This Oct! Book 3 Nts at W Chicago Lakeshore Fr $130+/Nt
Expedia
$130 Chicago, Illinois Book 3-Star Holiday Inn Chicago O'Hare in Chicago Fr $130+/Nt
Expedia
$159 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $159+/Nt
Expedia
$336 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Oct: $336 & Up
Save with Expedia, $60/night less
$79 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $79+/Nt
Expedia
$87 Chicago, Illinois Oct deal: Indigo Chicago Downtown Gold Coast Fr $87+/Nt
Expedia
$106 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $106+/Nt
Expedia
$103 Chicago, Illinois Hostelling International Chicago in Oct: $103 & Up
Expedia
$171 Chicago, Illinois Special deal: 4-Star Swissotel Chicago Fr $171+/Nt
Save with Expedia, $42/night less
$169 Chicago, Illinois Special deal: 4.5-Star Conrad Chicago Fr $169+/Nt
Expedia
$166 Chicago, Illinois Hampton Majestic Chicago Theatre District in Oct: $166 & Up
Expedia
$89 Chicago, Illinois Book the The Palmer House Hilton 3 Nts in Oct Fr $89+/Nt
Expedia
$85 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $85+/Nt
Expedia
$136 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $136+/Nt
Expedia
$144 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $144+/Nt
Expedia
$114 Chicago, Illinois Oct deal: BEST WESTERN River North Fr $114+/Nt
Expedia
$99 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $99+/Nt
Expedia
$108 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct at River Fr $108+/Nt
Save with Expedia, $11/night less
$104 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in Oct: $104 & Up
Expedia
$115 Chicago, Illinois Small budget: Book Days Inn Chicago 3 Nts in Oct Fr $115+/Nt
Expedia
$128 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $128+/Nt
Expedia
$260 Chicago, Illinois Chicago Savings! Book at Park Hyatt Chicago Fr $260+/Nt
Expedia
$119 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $119+/Nt
Save with Expedia, $7/night less
$130 Chicago, Illinois Save at 4-Star The Westin Chicago River North: $130 & Up in Oct
Expedia
$109 Chicago, Illinois Holiday Inn Express Cass on Sale: Book 3 Nts in Oct Fr $109+/Nt
Expedia
$317 Chicago, Illinois Chicago Savings! Book at The Peninsula Chicago Fr $317+/Nt
Save with Expedia, $158/night less
$68 Chicago, Illinois Book in Chicago: Save this Oct Fr $68+/Nt
Expedia
$109 Chicago, Illinois Save at 3-Star Holiday Inn Chicago Downtown: $109 & Up in Oct
Expedia
$79 Chicago, Illinois Chicago Savings! Book at Hyatt Regency McCormick Place Fr $79+/Nt
Expedia
$110 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $110+/Nt
Save with Expedia, $19/night less
$197 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $197+/Nt
Expedia
$116 Chicago, Illinois Book in Chicago: Save this Oct Fr $116+/Nt
Expedia
$116 Chicago, Illinois Felix on Sale: Book 3 Nts in Oct Fr $116+/Nt
Save with Expedia, $21/night less
$159 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $159+/Nt
Expedia
$119 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $119+/Nt
Expedia
$80 Chicago, Illinois BEST WESTERN Grant Park on Sale: Book 3 Nts in Oct Fr $80+/Nt
Save with Expedia, $20/night less
$149 Chicago, Illinois Book 4-Star Hyatt Chicago Magnificent Mile in Chicago Fr $149+/Nt
Expedia
$356 Chicago, Illinois Small budget: Book Four Seasons Chicago 3 Nts in Oct Fr $356+/Nt
Save with Expedia, $39/night less
$104 Chicago, Illinois Chicago Downtown, Autograph Collection in Oct: $104 & Up
Save with Expedia, $25/night less
$102 Chicago, Illinois Save at 4-Star Millennium Knickerbocker Chicago: $102 & Up in Oct
Save with Expedia, $17/night less
$161 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $161+/Nt
Save with Expedia, $69/night less
$109 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Oct: $109 & Up
Expedia
$128 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Omni Chicago Fr $128+/Nt
Save with Expedia, $31/night less
$139 Chicago, Illinois Oct deal: Hilton Chicago O'Hare Airport Fr $139+/Nt
Expedia
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $127+/Nt
Save with Expedia, $22/night less
$96 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct at The Whitehall Fr $96+/Nt
Save with Expedia, $23/night less
$102 Schiller Park, Illinois Book 3 Nts in Schiller Park this Oct Fr $102+/Nt
Expedia
$82 Deerfield, Illinois Book 3.5-Star Chicago Marriott Suites Deerfield Fr $82+/Nt
Save with Expedia, $27/night less
$104 Tinley Park, Illinois Book 3-Star Hilton Garden Inn Chicago/Tinley Park Fr $104+/Nt
Expedia
$221 Lombard, Illinois Westin Lombard Yorktown Center in Oct: $221 & Up
Expedia
$126 Itasca, Illinois Book the Eaglewood & Spa Chicago 3 Nts in Oct Fr $126+/Nt
Expedia
$99 Bloomingdale, Illinois Save at 3.5-Star Hilton Chicago/Indian Lakes: $99 & Up in Oct
Expedia
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$207 New York City, New York Cheap Flights from Detroit
DealBase.com
$297 New York City, New York Cheap Flights from Portland
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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