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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$123 Chicago, Illinois $123 & Up: The Whitehall 4-Star Hotel in Chicago
Save with Expedia, $53/night less
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$824 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $824
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$535 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $535
Expedia
$14 Chicago, Illinois Cheap Car Rentals in Chicago Fr $14/Day
CarRentals.com
$550 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $550
Expedia
$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
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$124 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $124+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$129 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $129+/Nt
Expedia
$169 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$140 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $140+/Nt
Expedia
$175 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$143 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $143+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$203 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $203+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$72 Chicago, Illinois Book 3-Star The Tremont Chicago at Magnificent Mile Fr $72+/Nt
Expedia
$96 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $96+/Nt
Expedia
$90 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $90+/Nt
Expedia
$103 Chicago, Illinois Book 4-Star Hilton Chicago Fr $103+/Nt
Expedia
$133 Chicago, Illinois Book 4-Star Raffaello in Chicago Fr $133+/Nt
Save with Expedia, $71/night less
$313 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $313+/Nt
Save with Expedia, $78/night less
$115 Chicago, Illinois Book in Chicago: Save this Oct Fr $115+/Nt
Expedia
$140 Chicago, Illinois Book in Chicago: Save this Oct Fr $140+/Nt
Expedia
$336 Chicago, Illinois Book in Chicago: Save this Oct Fr $336+/Nt
Save with Expedia, $60/night less
$93 Chicago, Illinois Book in Chicago: Save this Oct Fr $93+/Nt
Expedia
$97 Chicago, Illinois Book in Chicago: Save this Oct Fr $97+/Nt
Save with Expedia, $24/night less
$159 Chicago, Illinois Book the Comfort Suites Michigan Avenue 3 Nts in Oct Fr $159+/Nt
Expedia
$114 Chicago, Illinois Book the Holiday Inn Chicago Downtown 3 Nts in Oct Fr $114+/Nt
Expedia
$113 Chicago, Illinois Book the The Palmer House Hilton 3 Nts in Oct Fr $113+/Nt
Expedia
$133 Chicago, Illinois Book the Warwick Allerton Chicago 3 Nts in Oct Fr $133+/Nt
Save with Expedia, $90/night less
$866 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $866
Expedia
$1,680 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $1,680
Expedia
$139 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Kinzie Fr $139+/Nt
Expedia
$106 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $106+/Nt
Expedia
$113 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $113+/Nt
Expedia
$127 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $127+/Nt
Save with Expedia, $22/night less
$133 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $133+/Nt
Expedia
$137 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $137+/Nt
Save with Expedia, $12/night less
$159 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $159+/Nt
Expedia
$209 Chicago, Illinois Chicago Savings! Book at Conrad Chicago Fr $209+/Nt
Expedia
$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
$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
$158 Chicago, Illinois Chicago Savings! Book at Radisson Blu Aqua Fr $158+/Nt
Expedia
$166 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $166+/Nt
Expedia
$188 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $188+/Nt
Expedia
$126 Chicago, Illinois Congress Plaza in Oct: $126 & Up
Expedia
$152 Chicago, Illinois Embassy Suites Chicago Downtown in Oct: $152 & Up
Expedia
$152 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in Oct: $152 & Up
Expedia
$129 Chicago, Illinois MileNorth, A Chicago in Oct: $129 & Up
Expedia
$127 Chicago, Illinois Oct deal: Courtyard Chicago Downtown/Magnificent Mile Fr $127+/Nt
Expedia
$129 Chicago, Illinois Oct deal: Crowne Plaza Chicago - The Metro Fr $129+/Nt
Expedia
$150 Chicago, Illinois Oct deal: Fairmont Chicago Millennium Park Fr $150+/Nt
Save with Expedia, $16/night less
$179 Chicago, Illinois Oct deal: Hilton Suites Chicago/Magnificent Mile Fr $179+/Nt
Expedia
$128 Chicago, Illinois Oct deal: Holiday Inn Chicago Mart Plaza River North Fr $128+/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
$473 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $473
Expedia
$159 Chicago, Illinois Save at 3.5-Star Renaissance Chicago: $159 & Up in Oct
Expedia
$672 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $672
Expedia
$709 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $709
Expedia
$988 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $988
Expedia
$129 Chicago, Illinois Save at 4-Star JW Marriott Chicago: $129 & Up in Oct
Expedia
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts at Burnham - a Kimpton Fr $127+/Nt
Save with Expedia, $22/night less
$167 Chicago, Illinois Save Big This Oct! Book 3 Nts at The James Chicago Fr $167+/Nt
Save with Expedia, $29/night less
$104 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $104+/Nt
Save with Expedia, $25/night less
$171 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $171+/Nt
Expedia
$189 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $189+/Nt
Expedia
$198 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $198+/Nt
Expedia
$199 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $199+/Nt
Expedia
$208 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $208+/Nt
Save with Expedia, $51/night less
$94 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $94+/Nt
Expedia
$126 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct at Blake Chicago Fr $126+/Nt
Expedia
$116 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $116+/Nt
Expedia
$90 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $90+/Nt
Expedia
$99 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $99+/Nt
Expedia
$115 Chicago, Illinois Small budget: Book Days Inn Chicago 3 Nts in Oct Fr $115+/Nt
Expedia
$116 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $116+/Nt
Expedia
$127 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $127+/Nt
Expedia
$133 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $133+/Nt
Expedia
$183 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $183+/Nt
Expedia
$328 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $328+/Nt
Expedia
$93 Chicago, Illinois Special deal: 3-Star Chicago's Essex Inn Fr $93+/Nt
Save with Expedia, $16/night less
$169 Chicago, Illinois Special deal: 3.5-Star Buckingham Athletic Club Fr $169+/Nt
Expedia
$84 Chicago, Illinois Special deal: 3.5-Star River Fr $84+/Nt
Save with Expedia, $9/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
$109 Chicago, Illinois The Westin Michigan Avenue Chicago in Oct: $109 & Up
Expedia
$110 Addison, Illinois Addison Savings! Book at Hilton Garden Inn Addison Fr $110+/Nt
Expedia
PRICEDESTINATIONDEAL
$145 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$165 New York City, New York Cheap Flights from Milwaukee
DealBase.com
$225 New York City, New York Virgin America Current Lowest Fares
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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