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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$119 Chicago, Illinois $119 & Up: Palomar Chicago, a Kimpton 4-Star Hotel in Chicago
Save with Expedia, $20/night less
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$100 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $100+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$106 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $106+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$109 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $109+/Nt
Expedia
$110 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $110+/Nt
Expedia
$116 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $116+/Nt
Expedia
$120 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $120+/Nt
Expedia
$121 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $121+/Nt
Expedia
$126 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $126+/Nt
Expedia
$144 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $144+/Nt
Save with Expedia, $15/night less
$156 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $156+/Nt
Expedia
$159 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $159+/Nt
Expedia
$173 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $173+/Nt
Expedia
$299 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $299+/Nt
Expedia
$69 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $69+/Nt
Expedia
$99 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $99+/Nt
Expedia
$128 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $128+/Nt
Expedia
$146 Chicago, Illinois Book 4-Star Chicago Downtown, Autograph Collection Fr $146+/Nt
Save with Expedia, $37/night less
$149 Chicago, Illinois Book 4-Star Hyatt Chicago Magnificent Mile in Chicago Fr $149+/Nt
Expedia
$279 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $279+/Nt
Save with Expedia, $70/night less
$112 Chicago, Illinois Book in Chicago: Save this Oct Fr $112+/Nt
Save with Expedia, $7/night less
$116 Chicago, Illinois Book in Chicago: Save this Oct Fr $116+/Nt
Expedia
$119 Chicago, Illinois Book in Chicago: Save this Oct Fr $119+/Nt
Expedia
$136 Chicago, Illinois Book in Chicago: Save this Oct Fr $136+/Nt
Expedia
$139 Chicago, Illinois Book in Chicago: Save this Oct Fr $139+/Nt
Expedia
$143 Chicago, Illinois Book in Chicago: Save this Oct Fr $143+/Nt
Expedia
$188 Chicago, Illinois Book in Chicago: Save this Oct Fr $188+/Nt
Expedia
$127 Chicago, Illinois Book the Burnham - a Kimpton 3 Nts in Oct Fr $127+/Nt
Save with Expedia, $22/night less
$133 Chicago, Illinois Book the Raffaello 3 Nts in Oct Fr $133+/Nt
Save with Expedia, $71/night less
$156 Chicago, Illinois Book the Sofitel Chicago Water Tower 3 Nts in Oct Fr $156+/Nt
Expedia
$144 Chicago, Illinois Book the The Westin Chicago River North 3 Nts in Oct Fr $144+/Nt
Expedia
$153 Chicago, Illinois Book the W Chicago - City Center 3 Nts in Oct Fr $153+/Nt
Expedia
$159 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Conrad Chicago Fr $159+/Nt
Expedia
$128 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Omni Chicago Fr $128+/Nt
Save with Expedia, $31/night less
$111 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $111+/Nt
Expedia
$161 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $161+/Nt
Save with Expedia, $69/night less
$93 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $93+/Nt
Expedia
$99 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $99+/Nt
Save with Expedia, $25/night less
$99 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $99+/Nt
Expedia
$392 Chicago, Illinois Chicago Savings! Book at Four Seasons Chicago Fr $392+/Nt
Save with Expedia, $43/night less
$199 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $199+/Nt
Expedia
$149 Chicago, Illinois Chicago Savings! Book at Kinzie Fr $149+/Nt
Expedia
$129 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $129+/Nt
Expedia
$260 Chicago, Illinois Chicago Savings! Book at Park Hyatt Chicago Fr $260+/Nt
Expedia
$167 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $167+/Nt
Save with Expedia, $29/night less
$138 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $138+/Nt
Save with Expedia, $65/night less
$123 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Oct: $123 & Up
Expedia
$116 Chicago, Illinois Felix on Sale: Book 3 Nts in Oct Fr $116+/Nt
Save with Expedia, $21/night less
$148 Chicago, Illinois Hampton Inn & Suites Chicago - Downtown in Oct: $148 & Up
Expedia
$109 Chicago, Illinois Hampton Majestic Chicago Theatre District in Oct: $109 & Up
Expedia
$109 Chicago, Illinois Holiday Inn Express Cass on Sale: Book 3 Nts in Oct Fr $109+/Nt
Expedia
$194 Chicago, Illinois Holiday Inn Express Chicago-Midway Airport in Oct: $194 & Up
Expedia
$104 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in Oct: $104 & Up
Expedia
$103 Chicago, Illinois Hostelling International Chicago in Oct: $103 & Up
Expedia
$94 Chicago, Illinois Hyatt Regency Chicago in Oct: $94 & Up
Expedia
$115 Chicago, Illinois Indigo Chicago Downtown Gold Coast in Oct: $115 & Up
Expedia
$173 Chicago, Illinois Oct deal: Chicago's Essex Inn Fr $173+/Nt
Expedia
$139 Chicago, Illinois Oct deal: Hilton Chicago O'Hare Airport Fr $139+/Nt
Expedia
$127 Chicago, Illinois Oct deal: PUBLIC Chicago Fr $127+/Nt
Save with Expedia, $68/night less
$119 Chicago, Illinois Oct deal: W Chicago Lakeshore Fr $119+/Nt
Expedia
$88 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Oct: $88 & Up
Save with Expedia, $22/night less
$140 Chicago, Illinois Residence Inn Chicago Downtown / River North in Oct: $140 & Up
Expedia
$156 Chicago, Illinois Save at 3-Star Residence Inn Chicago Downtown: $156 & Up in Oct
Expedia
$102 Chicago, Illinois Save at 4-Star Millennium Knickerbocker Chicago: $102 & Up in Oct
Save with Expedia, $17/night less
$103 Chicago, Illinois Save Big This Oct! Book 3 Nts at Hilton Chicago Fr $103+/Nt
Expedia
$110 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $110+/Nt
Expedia
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $127+/Nt
Save with Expedia, $22/night less
$128 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $128+/Nt
Expedia
$135 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $135+/Nt
Expedia
$152 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $152+/Nt
Expedia
$159 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $159+/Nt
Expedia
$159 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $159+/Nt
Expedia
$166 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $166+/Nt
Expedia
$85 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $85+/Nt
Save with Expedia, $14/night less
$78 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct at Congress Plaza Fr $78+/Nt
Expedia
$96 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct at The Whitehall Fr $96+/Nt
Save with Expedia, $23/night less
$113 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $113+/Nt
Expedia
$236 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $236+/Nt
Expedia
$115 Chicago, Illinois Small budget: Book Days Inn Chicago 3 Nts in Oct Fr $115+/Nt
Expedia
$112 Chicago, Illinois Small budget: Book Radisson Blu Aqua 3 Nts in Oct Fr $112+/Nt
Expedia
$108 Chicago, Illinois Special deal: 3.5-Star Blake Chicago Fr $108+/Nt
Save with Expedia, $18/night less
$179 Chicago, Illinois Special deal: 3.5-Star Hyatt Regency McCormick Place Fr $179+/Nt
Expedia
$171 Chicago, Illinois Special deal: 4-Star Swissotel Chicago Fr $171+/Nt
Save with Expedia, $42/night less
$115 Chicago, Illinois Special deal: 4-Star theWit - A DoubleTree by Hilton Fr $115+/Nt
Expedia
$128 Chicago, Illinois Special deal: 4.5-Star InterContinental Chicago Fr $128+/Nt
Expedia
$370 Chicago, Illinois The Peninsula Chicago in Oct: $370 & Up
Save with Expedia, $185/night less
$336 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Oct: $336 & Up
Save with Expedia, $60/night less
$144 Chicago, Illinois The Silversmith on Sale: Book 3 Nts in Oct Fr $144+/Nt
Save with Expedia, $25/night less
$68 Chicago, Illinois Travelodge Chicago Downtown on Sale: Book 3 Nts in Oct Fr $68+/Nt
Expedia
$170 Chicago, Illinois Wyndham Grand Chicago Riverfront in Oct: $170 & Up
Save with Expedia, $29/night less
$166 Itasca, Illinois $166 & Up: Westin Chicago Northwest 4-Star Hotel in Itasca
Expedia
$108 Addison, Illinois Addison Savings! Book 3 Nts in Oct Fr $108+/Nt
Expedia
$72 Bensenville, Illinois Bensenville Savings! Book 3 Nts in Oct Fr $72+/Nt
Expedia
$86 Burbank, Illinois BEST WESTERN Inn & Suites - Midway Airport in Oct: $86 & Up
Save with Expedia, $21/night less
$115 Bolingbrook, Illinois Bolingbrook Savings! Book at aloft Bolingbrook Fr $115+/Nt
Expedia
$209 Rosemont, Illinois Book 3 Nts in Rosemont this Oct Fr $209+/Nt
Expedia
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$84 New York City, New York JetBlue Boo to High Fares Sale
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$253 New York City, New York Cheap Flights from Atlanta
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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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