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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$125 Chicago, Illinois Cheap Flights from Washington, DC
DealBase.com
$165 Chicago, Illinois Fly for Less! Washington DC to Chicago From $165 R/T*
Expedia
$265 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$165 Chicago, Illinois Fly for Less! Denver to Chicago From $165 R/T*
Expedia
$115 Chicago, Illinois Cheap Flights from Atlanta
DealBase.com
$195 Chicago, Illinois Hot Flight Deal! Philadelphia to Chicago Fr $195 R/T*
Expedia
$255 Chicago, Illinois Cheap Flights from Portland
DealBase.com
$295 Chicago, Illinois Chicago on Sale! Fly From Los Angeles From $295 R/T*
Expedia
$165 Chicago, Illinois Cheap Flights from Baltimore
DealBase.com
$235 Chicago, Illinois Hot Flight Deal! Boston to Chicago Fr $235 R/T*
Expedia
$94 Chicago, Illinois Delta US Flights on Sale
DealBase.com
$355 Chicago, Illinois Fly for Less! Seattle to Chicago From $355 R/T*
Expedia
$195 Chicago, Illinois Cheap Flights from New York
DealBase.com
$163 Chicago, Illinois Book 3-Star Holiday Inn Express Cass in Chicago Fr $163+/Nt
Expedia
$145 Chicago, Illinois Cheap Flights from Denver
DealBase.com
$146 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $146+/Nt
Expedia
$150 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$208 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $208+/Nt
Save with Expedia, $36/night less
$227 Chicago, Illinois Cheap Flights from Raleigh
DealBase.com
$229 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $229+/Nt
Save with Expedia, $40/night less
$95 Chicago, Illinois Cheap Flights from Minneapolis
DealBase.com
$239 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $239+/Nt
Expedia
$291 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$243 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $243+/Nt
Expedia
$227 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$428 Chicago, Illinois Trump International & Tower Chicago in Sep: $428 & Up
Save with Expedia, $107/night less
$277 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$208 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $208+/Nt
Expedia
$115 Chicago, Illinois Cheap Flights from Dallas
DealBase.com
$242 Chicago, Illinois Book 4.5-Star InterContinental Chicago Fr $242+/Nt
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$169 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $169+/Nt
Expedia
$273 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$203 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $203+/Nt
Expedia
$205 Chicago, Illinois Cheap Flights from Salt Lake City
DealBase.com
$212 Chicago, Illinois Book in Chicago: Save this Sep Fr $212+/Nt
Save with Expedia, $11/night less
$328 Chicago, Illinois Cheap Flights from Miami
DealBase.com
$208 Chicago, Illinois Save at 4.5-Star Omni Chicago: $208 & Up in Sep
Save with Expedia, $51/night less
$115 Chicago, Illinois Cheap Flights from Boston
DealBase.com
$186 Chicago, Illinois Book 3-Star Chicago's Essex Inn in Chicago Fr $186+/Nt
Expedia
$251 Chicago, Illinois Cheap Flights from Seattle
DealBase.com
$276 Chicago, Illinois Book the The Blackstone A Renaissance 3 Nts in Sep Fr $276+/Nt
Expedia
$265 Chicago, Illinois Cheap Flights from San Francisco
DealBase.com
$269 Chicago, Illinois Sep deal: theWit - A DoubleTree by Hilton Fr $269+/Nt
Expedia
$135 Chicago, Illinois Cheap Flights from Orlando
DealBase.com
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$226 Chicago, Illinois Cheap Flights from Newark
DealBase.com
$221 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $221+/Nt
Save with Expedia, $38/night less
$109 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$257 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $257+/Nt
Expedia
$275 Chicago, Illinois Cheap Flights from Los Angeles
DealBase.com
$156 Chicago, Illinois Book 3-Star Holiday Inn Chicago Downtown Fr $156+/Nt
Expedia
$284 Chicago, Illinois Cheap Flights from Philadelphia
DealBase.com
$201 Chicago, Illinois Special deal: 4-Star Sheraton Chicago and Towers Fr $201+/Nt
Expedia
$181 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$130 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $130+/Nt
Expedia
$253 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$174 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $174+/Nt
Expedia
$128 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$229 Chicago, Illinois Burnham - a Kimpton in Sep: $229 & Up
Expedia
$173 Chicago, Illinois Cheap Flights from Houston
DealBase.com
$237 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $237+/Nt
Expedia
$122 Chicago, Illinois Delta US Flights on Sale
DealBase.com
$136 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $136+/Nt
Expedia
$187 Chicago, Illinois Cheap Flights from St. Louis
DealBase.com
$283 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $283+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$213 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep at Kinzie Fr $213+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$306 Chicago, Illinois The Westin Chicago River North in Sep: $306 & Up
Expedia
$99+ Chicago, Illinois Save Up To 25% on 4-Star Chicago Hotels
trivago
$99 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $99+/Nt
Expedia
$220 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $220+/Nt
Expedia
$362 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $362+/Nt
Expedia
$188 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $188+/Nt
Save with Expedia, $102/night less
$239 Chicago, Illinois Small budget: Book Hard Rock Chicago 3 Nts in Sep Fr $239+/Nt
Expedia
$205 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $205+/Nt
Save with Expedia, $51/night less
$208 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $208+/Nt
Expedia
$219 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $219+/Nt
Expedia
$189 Chicago, Illinois Book the The Drake 3 Nts in Sep Fr $189+/Nt
Expedia
$160 Chicago, Illinois Book 3.5-Star River Fr $160+/Nt
Save with Expedia, $6/night less
$392 Chicago, Illinois Four Seasons Chicago on Sale: Book 3 Nts in Sep Fr $392+/Nt
Save with Expedia, $43/night less
$180 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $180+/Nt
Expedia
$190 Chicago, Illinois Book 3-Star BEST WESTERN River North Fr $190+/Nt
Expedia
$206 Chicago, Illinois Special deal: 4-Star dana and spa Fr $206+/Nt
Expedia
$126 Chicago, Illinois Special deal: 3-Star Congress Plaza Fr $126+/Nt
Expedia
$169 Chicago, Illinois $169 & Up: Hilton Chicago O'Hare Airport 4-Star Hotel in Chicago
Expedia
$283 Chicago, Illinois Save Big This Sep! Book 3 Nts at Radisson Blu Aqua Fr $283+/Nt
Expedia
$193 Chicago, Illinois Sep deal: Club Quarters Chicago - Central Loop Fr $193+/Nt
Save with Expedia, $6/night less
$254 Chicago, Illinois Chicago Downtown, Autograph Collection in Sep: $254 & Up
Expedia
$196 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $196+/Nt
Save with Expedia, $35/night less
$245 Chicago, Illinois Book the Swissotel Chicago 3 Nts in Sep Fr $245+/Nt
Save with Expedia, $62/night less
$206 Chicago, Illinois Chicago Savings! Book at The Silversmith Fr $206+/Nt
Save with Expedia, $37/night less
$330 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Sep: $330 & Up
Save with Expedia, $165/night less
$199 Chicago, Illinois Hyatt Regency Chicago in Sep: $199 & Up
Expedia
$229 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $229+/Nt
Expedia
$299 Chicago, Illinois Save at 4-Star JW Marriott Chicago: $299 & Up in Sep
Expedia
$236 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $236+/Nt
Expedia
$179 Chicago, Illinois $179 & Up: Comfort Suites Michigan Avenue 3-Star Hotel in Chicago
Expedia
$152 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $152+/Nt
Save with Expedia, $38/night less
PRICEDESTINATIONDEAL
$145 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$323 New York City, New York Cheap Flights from San Diego
DealBase.com
$196 New York City, New York Cheap Flights from Tampa
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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