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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$145 Chicago, Illinois Cheap Flights from Washington, DC
DealBase.com
$189 Chicago, Illinois $189 & Up: The Palmer House Hilton 4-Star Hotel in Chicago
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$219 Chicago, Illinois $219 & Up: InterContinental Chicago 4.5-Star Hotel in Chicago
Expedia
$320 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/3/14
DealBase.com
$385 Chicago, Illinois $385 & Up: Four Seasons Chicago 5-Star Hotel in Chicago
Expedia
$265 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$365 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $365
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$499 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $499
Expedia
$247 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$133 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $133+/Nt
Save with Expedia, $23/night less
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$143 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $143+/Nt
Expedia
$225 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$147 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $147+/Nt
Expedia
$337 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$170 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $170+/Nt
Expedia
$287 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$184 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $184+/Nt
Expedia
$209 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$226 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $226+/Nt
Expedia
$115 Chicago, Illinois Cheap Flights from Atlanta
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$169 Chicago, Illinois Book 3-Star Comfort Suites Michigan Avenue Fr $169+/Nt
Expedia
$165 Chicago, Illinois Cheap Flights from Baltimore
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$229 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $229+/Nt
Expedia
$135 Chicago, Illinois Cheap Flights from Boston
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$236 Chicago, Illinois Book 3.5-Star Buckingham Athletic Club Fr $236+/Nt
Expedia
$115 Chicago, Illinois Cheap Flights from Dallas
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$162 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $162+/Nt
Save with Expedia, $11/night less
$135 Chicago, Illinois Cheap Flights from Denver
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$189 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $189+/Nt
Expedia
$173 Chicago, Illinois Cheap Flights from Houston
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$169 Chicago, Illinois Book 3.5-Star Embassy Suites Chicago Downtown Fr $169+/Nt
Expedia
$275 Chicago, Illinois Cheap Flights from Los Angeles
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$216 Chicago, Illinois Book 3.5-Star Kinzie Fr $216+/Nt
Expedia
$339 Chicago, Illinois Cheap Flights from Miami
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$239 Chicago, Illinois Book 4-Star Hyatt Regency Chicago in Chicago Fr $239+/Nt
Expedia
$95 Chicago, Illinois Cheap Flights from Minneapolis
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$246 Chicago, Illinois Book 4-Star JW Marriott Chicago Fr $246+/Nt
Expedia
$155 Chicago, Illinois Cheap Flights from New Orleans
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$367 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $367+/Nt
Save with Expedia, $92/night less
$195 Chicago, Illinois Cheap Flights from New York
DealBase.com
$110 Chicago, Illinois Book in Chicago: Save this Oct Fr $110+/Nt
Save with Expedia, $27/night less
$226 Chicago, Illinois Cheap Flights from Newark
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$167 Chicago, Illinois Book in Chicago: Save this Oct Fr $167+/Nt
Expedia
$295 Chicago, Illinois Cheap Flights from Philadelphia
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$199 Chicago, Illinois Book in Chicago: Save this Oct Fr $199+/Nt
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$185 Chicago, Illinois Cheap Flights from Phoenix
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$203 Chicago, Illinois Book in Chicago: Save this Oct Fr $203+/Nt
Expedia
$235 Chicago, Illinois Cheap Flights from Portland
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$207 Chicago, Illinois Book in Chicago: Save this Oct Fr $207+/Nt
Expedia
$98 Chicago, Illinois Cheap Flights from Salt Lake City
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$215 Chicago, Illinois Book in Chicago: Save this Oct Fr $215+/Nt
Expedia
$283 Chicago, Illinois Cheap Flights from San Diego
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$219 Chicago, Illinois Book in Chicago: Save this Oct Fr $219+/Nt
Expedia
$255 Chicago, Illinois Cheap Flights from San Francisco
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$236 Chicago, Illinois Book in Chicago: Save this Oct Fr $236+/Nt
Expedia
$290 Chicago, Illinois Cheap Flights from Seattle
DealBase.com
$415 Chicago, Illinois Book in Chicago: Save this Oct Fr $415+/Nt
Expedia
$187 Chicago, Illinois Cheap Flights from St. Louis
DealBase.com
$150 Chicago, Illinois Book the BEST WESTERN River North 3 Nts in Oct Fr $150+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$112 Chicago, Illinois Book the Days Inn Chicago 3 Nts in Oct Fr $112+/Nt
Expedia
$127 Chicago, Illinois Delta US Flights on Sale
DealBase.com
$492 Chicago, Illinois Book the The Peninsula Chicago 3 Nts in Oct Fr $492+/Nt
Expedia
$99 Chicago, Illinois Delta US Flights on Sale
DealBase.com
$901 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $901
Expedia
$42 Chicago, Illinois Frontier Airlines $49 Sale
DealBase.com
$126 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Congress Plaza Fr $126+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$133 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $133+/Nt
Save with Expedia, $71/night less
$99+ Chicago, Illinois Save Up To 25% on 4-Star Chicago Hotels
trivago
$138 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $138+/Nt
Save with Expedia, $25/night less
$129 Chicago, Illinois Southwest Airlines Atlanta Specials
DealBase.com
$143 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $143+/Nt
Expedia
$113 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$161 Chicago, Illinois Chicago Savings! Book at ACME Company Chicago Fr $161+/Nt
Save with Expedia, $28/night less
$155 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$143 Chicago, Illinois Chicago Savings! Book at Blake Chicago Fr $143+/Nt
Expedia
$123 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$215 Chicago, Illinois Chicago Savings! Book at Conrad Chicago Fr $215+/Nt
Expedia
$133 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$140 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $140+/Nt
Expedia
$89 Chicago, Illinois Sun Country Airlines Fall Fare Sale
DealBase.com
$186 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $186+/Nt
Expedia
$133 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$229 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $229+/Nt
Expedia
$203 Chicago, Illinois Chicago Savings! Book at Radisson Blu Aqua Fr $203+/Nt
Expedia
$250 Chicago, Illinois Chicago Savings! Book at Swissotel Chicago Fr $250+/Nt
Expedia
$221 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $221+/Nt
Save with Expedia, $38/night less
$109 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $109+/Nt
Expedia
$325 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $325+/Nt
Expedia
$383 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $383+/Nt
Expedia
$189 Chicago, Illinois Crowne Plaza Chicago Magnificent Mile in Oct: $189 & Up
Expedia
$253 Chicago, Illinois Fairmont Chicago Millennium Park in Oct: $253 & Up
Expedia
$184 Chicago, Illinois Hard Rock Chicago in Oct: $184 & Up
Save with Expedia, $32/night less
$179 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in Oct: $179 & Up
Expedia
$112 Chicago, Illinois Indigo Chicago Downtown Gold Coast in Oct: $112 & Up
Expedia
PRICEDESTINATIONDEAL
$145 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$215 New York City, New York American Airlines US Flight Deals
DealBase.com
$324 New York City, New York Cheap Flights from San Francisco
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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