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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$73 Chicago, Illinois Save in Chicago: Book 3 Nts in Dec Fr $73+/Nt
Expedia
$170+ Chicago, Illinois $170: Warwick Allerton Hotel Chicago
Hotels.com
$79 Chicago, Illinois Book in Chicago: Save this Dec Fr $79+/Nt
Expedia
$34 Chicago, Illinois Spirit Airlines Be Home for Christmas Sale
DealBase.com
$898 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $898
Expedia
$34 Chicago, Illinois Spirit Airlines Be Home for Christmas Sale
DealBase.com
$85 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Dec: $85 & Up
Expedia
$34 Chicago, Illinois Spirit Airlines Be Home for Christmas Sale
DealBase.com
$1,202 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,202
Expedia
$157+ Chicago, Illinois $157: The Buckingham Athletic Club & Hotel, Chicago
Priceline.com
$104 Chicago, Illinois The Westin Michigan Avenue Chicago in Dec: $104 & Up
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$96 Chicago, Illinois Save Big This Dec! Book 3 Nts at Felix Fr $96+/Nt
Save with Expedia, $17/night less
$175+ Chicago, Illinois $175: PUBLIC Chicago
Priceline.com
$1,068 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $1,068
Expedia
$34 Chicago, Illinois Spirit Airlines Be Home for Christmas Sale
DealBase.com
$89 Chicago, Illinois Hilton Suites Chicago/Magnificent Mile in Dec: $89 & Up
Expedia
$34 Chicago, Illinois Spirit Airlines Be Home for Christmas Sale
DealBase.com
$99 Chicago, Illinois Special deal: 4.5-Star InterContinental Chicago Fr $99+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$244 Chicago, Illinois Chicago Savings! Book at Park Hyatt Chicago Fr $244+/Nt
Expedia
$135 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$88 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $88+/Nt
Save with Expedia, $41/night less
$117 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$1,027 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,027
Expedia
$275 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$60 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Dec: $60 & Up
Save with Expedia, $15/night less
$132+ Chicago, Illinois $132: SpringHill Suites Chicago O'Hare by Marriott
Priceline.com
$2,213 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $2,213
Expedia
$112 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$99 Chicago, Illinois Save Big This Dec! Book 3 Nts in Chicago Fr $99+/Nt
Expedia
$103+ Chicago, Illinois $103: Millennium Knickerbocker, Chicago
Hotels.com
$81 Chicago, Illinois River in Dec: $81 & Up
Save with Expedia, $8/night less
$133 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$165 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $165+/Nt
Expedia
$291 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$82 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $82+/Nt
Save with Expedia, $27/night less
$213 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$116 Chicago, Illinois Chicago Savings! Book at Radisson Blu Aqua Fr $116+/Nt
Expedia
$122+ Chicago, Illinois $122: The Willows Hotel, Chicago
Priceline.com
$93 Chicago, Illinois Save in Chicago: Book 3 Nts in Dec Fr $93+/Nt
Save with Expedia, $16/night less
$135+ Chicago, Illinois $135: Conrad Chicago
Priceline.com
$81 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $81+/Nt
Save with Expedia, $14/night less
$34 Chicago, Illinois Spirit Airlines Be Home for Christmas Sale
DealBase.com
$126 Chicago, Illinois Book 3.5-Star Kinzie in Chicago Fr $126+/Nt
Expedia
$225 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$159 Chicago, Illinois Save in Chicago: Book 3 Nts in Dec Fr $159+/Nt
Expedia
$241 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$119 Chicago, Illinois Book the Buckingham Athletic Club 3 Nts in Dec Fr $119+/Nt
Save with Expedia, $20/night less
$126+ Chicago, Illinois $126: Kinzie Hotel, Chicago
Priceline.com
$294 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $294+/Nt
Expedia
$139 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$120 Chicago, Illinois Save Big This Dec! Book 3 Nts in Chicago Fr $120+/Nt
Save with Expedia, $13/night less
$271 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$120 Chicago, Illinois Save Big This Dec! Book 3 Nts in Chicago Fr $120+/Nt
Save with Expedia, $30/night less
$239 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$284 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Dec: $284 & Up
Save with Expedia, $141/night less
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$129 Chicago, Illinois Special deal: 4-Star dana and spa Fr $129+/Nt
Expedia
$164 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$159 Chicago, Illinois Special deal: 4-Star JW Marriott Chicago Fr $159+/Nt
Expedia
$113 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$284 Chicago, Illinois Save Big This Dec! Book 3 Nts in Chicago Fr $284+/Nt
Save with Expedia, $141/night less
$153 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$100 Chicago, Illinois Book in Chicago: Save this Dec Fr $100+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$89 Chicago, Illinois Special deal: 3-Star Comfort Suites Michigan Avenue Fr $89+/Nt
Expedia
$126 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$92 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $92+/Nt
Expedia
$189+ Chicago, Illinois $189: Springhill Suites Chicago Downtown/ River North
Priceline.com
$2,113 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $2,113
Expedia
$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
Priceline.com
$116 Chicago, Illinois Save Big This Dec! Book 3 Nts in Chicago Fr $116+/Nt
Expedia
$140 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$129 Chicago, Illinois Chicago Marriott Downtown Magnificent Mile in Dec: $129 & Up
Expedia
$90 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$99 Chicago, Illinois Book 3-Star Congress Plaza Fr $99+/Nt
Expedia
$31 Chicago, Illinois Chicago Vacation Rental Deals From $31
Tripping
$110 Chicago, Illinois Book 3.5-Star The Silversmith Fr $110+/Nt
Save with Expedia, $19/night less
$34 Chicago, Illinois Spirit Airlines Be Home for Christmas Sale
DealBase.com
$93 Chicago, Illinois Dec deal: La Quinta Inn & Suites Chicago Downtown Fr $93+/Nt
Expedia
$114 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$100 Chicago, Illinois Save in Chicago: Book 3 Nts in Dec Fr $100+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$97 Chicago, Illinois Hilton Chicago on Sale: Book 3 Nts in Dec Fr $97+/Nt
Expedia
$129+ Chicago, Illinois $129: Raffaello Hotel, Chicago
Hotels.com
$88 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $88+/Nt
Save with Expedia, $58/night less
$279 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$94 Chicago, Illinois Save at 3-Star BEST WESTERN River North: $94 & Up in Dec
Expedia
$212+ Chicago, Illinois $212: Fairmont Chicago at Millennium Park
Hotels.com
$108 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec at Raffaello Fr $108+/Nt
Save with Expedia, $58/night less
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$79 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $79+/Nt
Expedia
$139 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$126 Chicago, Illinois Book in Chicago: Save this Dec Fr $126+/Nt
Save with Expedia, $13/night less
$158+ Chicago, Illinois $158: dana hotel and spa, Chicago
Priceline.com
$89 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $89+/Nt
Expedia
$188+ Chicago, Illinois $188: The James Chicago
Hotels.com
$102 Chicago, Illinois Book 4-Star W Chicago Lakeshore Fr $102+/Nt
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
PRICEDESTINATIONDEAL
$117 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$200 New York City, New York Virgin America Current Lowest Fares
DealBase.com
$219 New York City, New York Cheap Flights from Milwaukee
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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