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Chicago, IL Hotel Deals

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Chicago, IL Hotel Deals

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TYPE PRICE DESTINATION DEAL
$116 Chicago, Illinois $116 & Up: Felix 4-Star Hotel in Chicago
Save with Expedia, $21/night less
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
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$123 Chicago, Illinois $123 & Up: The Whitehall 4-Star Hotel in Chicago
Save with Expedia, $53/night less
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$133 Chicago, Illinois $133 & Up: Chicago's Essex Inn 3-Star Hotel in Chicago
Save with Expedia, $23/night less
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$103 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $103+/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
$124 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $124+/Nt
Expedia
$140 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $140+/Nt
Expedia
$143 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $143+/Nt
Expedia
$72 Chicago, Illinois Book 3-Star The Tremont Chicago at Magnificent Mile Fr $72+/Nt
Expedia
$116 Chicago, Illinois Book 3.5-Star Central Loop Fr $116+/Nt
Expedia
$96 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $96+/Nt
Expedia
$138 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $138+/Nt
Expedia
$176 Chicago, Illinois Book 4-Star Chicago Downtown, Autograph Collection Fr $176+/Nt
Save with Expedia, $43/night less
$103 Chicago, Illinois Book 4-Star Hilton Chicago Fr $103+/Nt
Expedia
$195 Chicago, Illinois Book 4-Star PUBLIC Chicago Fr $195+/Nt
Expedia
$136 Chicago, Illinois Book 4-Star Raffaello Fr $136+/Nt
Save with Expedia, $73/night less
$136 Chicago, Illinois Book 4-Star W Chicago - City Center in Chicago Fr $136+/Nt
Expedia
$128 Chicago, Illinois Book 4.5-Star Omni Chicago Fr $128+/Nt
Save with Expedia, $31/night less
$344 Chicago, Illinois Book 5-Star Waldorf Astoria Chicago Fr $344+/Nt
Expedia
$104 Chicago, Illinois Book in Chicago: Save this Oct Fr $104+/Nt
Expedia
$115 Chicago, Illinois Book in Chicago: Save this Oct Fr $115+/Nt
Expedia
$119 Chicago, Illinois Book in Chicago: Save this Oct Fr $119+/Nt
Save with Expedia, $30/night less
$156 Chicago, Illinois Book in Chicago: Save this Oct Fr $156+/Nt
Expedia
$179 Chicago, Illinois Book in Chicago: Save this Oct Fr $179+/Nt
Expedia
$336 Chicago, Illinois Book in Chicago: Save this Oct Fr $336+/Nt
Save with Expedia, $60/night less
$97 Chicago, Illinois Book in Chicago: Save this Oct Fr $97+/Nt
Expedia
$112 Chicago, Illinois Book the Radisson Blu Aqua 3 Nts in Oct Fr $112+/Nt
Expedia
$189 Chicago, Illinois Book the Residence Inn Chicago Downtown 3 Nts in Oct Fr $189+/Nt
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$113 Chicago, Illinois Book the The Palmer House Hilton 3 Nts in Oct Fr $113+/Nt
Expedia
$158 Chicago, Illinois Book the The Westin Chicago River North 3 Nts in Oct Fr $158+/Nt
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$109 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Blake Chicago Fr $109+/Nt
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$106 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $106+/Nt
Expedia
$110 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $110+/Nt
Save with Expedia, $19/night less
$127 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $127+/Nt
Save with Expedia, $22/night less
$129 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $129+/Nt
Expedia
$135 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $135+/Nt
Expedia
$136 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $136+/Nt
Save with Expedia, $23/night less
$170 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $170+/Nt
Save with Expedia, $29/night less
$176 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $176+/Nt
Expedia
$81 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $81+/Nt
Save with Expedia, $8/night less
$99 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $99+/Nt
Expedia
$209 Chicago, Illinois Chicago Savings! Book at Conrad Chicago Fr $209+/Nt
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$166 Chicago, Illinois Chicago Savings! Book at dana and spa Fr $166+/Nt
Expedia
$392 Chicago, Illinois Chicago Savings! Book at Four Seasons Chicago Fr $392+/Nt
Save with Expedia, $43/night less
$135 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $135+/Nt
Expedia
$79 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $79+/Nt
Expedia
$79 Chicago, Illinois Chicago Savings! Book at Hyatt Regency McCormick Place Fr $79+/Nt
Expedia
$179 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $179+/Nt
Expedia
$121 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $121+/Nt
Save with Expedia, $52/night less
$119 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $119+/Nt
Save with Expedia, $20/night less
$156 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $156+/Nt
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$188 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $188+/Nt
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$195 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $195+/Nt
Save with Expedia, $34/night less
$317 Chicago, Illinois Chicago Savings! Book at The Peninsula Chicago Fr $317+/Nt
Save with Expedia, $158/night less
$109 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $109+/Nt
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$138 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $138+/Nt
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$179 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Oct: $179 & Up
Expedia
$123 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Oct: $123 & Up
Expedia
$152 Chicago, Illinois Embassy Suites Chicago Downtown in Oct: $152 & Up
Expedia
$167 Chicago, Illinois Holiday Inn Chicago Mart Plaza River North in Oct: $167 & Up
Expedia
$129 Chicago, Illinois MileNorth, A Chicago in Oct: $129 & Up
Expedia
$109 Chicago, Illinois Oct deal: Crowne Plaza Chicago - The Metro Fr $109+/Nt
Expedia
$179 Chicago, Illinois Oct deal: Hilton Suites Chicago/Magnificent Mile Fr $179+/Nt
Expedia
$149 Chicago, Illinois Oct deal: Hyatt Chicago Magnificent Mile Fr $149+/Nt
Expedia
$102 Chicago, Illinois Oct deal: Millennium Knickerbocker Chicago Fr $102+/Nt
Save with Expedia, $17/night less
$168 Chicago, Illinois Oct deal: Swissotel Chicago Fr $168+/Nt
Save with Expedia, $42/night less
$260 Chicago, Illinois Park Hyatt Chicago on Sale: Book 3 Nts in Oct Fr $260+/Nt
Expedia
$203 Chicago, Illinois Save at 3.5-Star Buckingham Athletic Club: $203 & Up in Oct
Expedia
$159 Chicago, Illinois Save at 3.5-Star Renaissance Chicago: $159 & Up in Oct
Expedia
$144 Chicago, Illinois Save at 4-Star Fairmont Chicago Millennium Park: $144 & Up in Oct
Save with Expedia, $15/night less
$109 Chicago, Illinois Save at 4-Star Warwick Allerton Chicago: $109 & Up in Oct
Save with Expedia, $75/night less
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts at Burnham - a Kimpton Fr $127+/Nt
Save with Expedia, $22/night less
$109 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $109+/Nt
Expedia
$199 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $199+/Nt
Expedia
$139 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $139+/Nt
Expedia
$149 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $149+/Nt
Expedia
$99 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $99+/Nt
Expedia
$189 Chicago, Illinois Sheraton Chicago and Towers in Oct: $189 & Up
Expedia
$115 Chicago, Illinois Small budget: Book Days Inn Chicago 3 Nts in Oct Fr $115+/Nt
Expedia
$206 Chicago, Illinois Small budget: Book Kinzie 3 Nts in Oct Fr $206+/Nt
Expedia
$100 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $100+/Nt
Expedia
$116 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $116+/Nt
Expedia
$196 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $196+/Nt
Expedia
$279 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $279+/Nt
Save with Expedia, $70/night less
$139 Chicago, Illinois Special deal: 4-Star Hilton Chicago O'Hare Airport Fr $139+/Nt
Expedia
$88 Chicago, Illinois Special deal: 4.5-Star InterContinental Chicago Fr $88+/Nt
Expedia
$121 Chicago, Illinois The Westin Michigan Avenue Chicago in Oct: $121 & Up
Expedia
$110 Addison, Illinois Addison Savings! Book at Hilton Garden Inn Addison Fr $110+/Nt
Expedia
$102 Alsip, Illinois Alsip Savings! Book at Doubletree Chicago / Alsip Fr $102+/Nt
Expedia
$73 Countryside, Illinois BEST WESTERN Chicagoland - Countryside in Oct: $73 & Up
Save with Expedia, $18/night less
$109 Downers Grove, Illinois Book 3 Nts in Downers Grove this Oct Fr $109+/Nt
Expedia
$104 Tinley Park, Illinois Book 3 Nts in Tinley Park this Oct Fr $104+/Nt
Expedia
$115 Bolingbrook, Illinois Book 3-Star aloft Bolingbrook Fr $115+/Nt
Expedia
$79 Oakbrook Terrace, Illinois Book 3-Star Hilton Garden Inn Oakbrook Terrace Fr $79+/Nt
Expedia
$126 Skokie, Illinois Book 3-Star Holiday Inn Chicago North Shore (Skokie) Fr $126+/Nt
Expedia
$149 Oak Brook, Illinois Book 4-Star The Hyatt Lodge at McDonald's Campus Fr $149+/Nt
Expedia
PRICEDESTINATIONDEAL
$145 New York City, New York Cheap Flights from Washington, DC
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$165 New York City, New York Cheap Flights from Milwaukee
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$225 New York City, New York Virgin America Current Lowest Fares
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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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