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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
$126 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $126+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$259 Chicago, Illinois Chicago Savings! Book at Swissotel Chicago Fr $259+/Nt
Save with Expedia, $64/night less
$99+ Chicago, Illinois Save Up To 25% on 4-Star Chicago Hotels
trivago
$145 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $145+/Nt
Expedia
$228 Chicago, Illinois United Airlines Weekend Specials for 9/19/14
DealBase.com
$152 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $152+/Nt
Save with Expedia, $38/night less
$195 Chicago, Illinois Cheap Flights from New York
DealBase.com
$226 Chicago, Illinois Book in Chicago: Save at the Hard Rock Chicago in Sep Fr $226+/Nt
Expedia
$226 Chicago, Illinois Cheap Flights from Newark
DealBase.com
$196 Chicago, Illinois Book in Chicago: Save this Sep Fr $196+/Nt
Expedia
$227 Chicago, Illinois Cheap Flights from Raleigh
DealBase.com
$299 Chicago, Illinois Book 4-Star JW Marriott Chicago Fr $299+/Nt
Expedia
$115 Chicago, Illinois Cheap Flights from Atlanta
DealBase.com
$141 Chicago, Illinois Special deal: 3-Star Chicago South Loop Fr $141+/Nt
Save with Expedia, $25/night less
$228 Chicago, Illinois United Airlines Weekend Specials for 9/19/14
DealBase.com
$362 Chicago, Illinois Sep deal: Park Hyatt Chicago Fr $362+/Nt
Expedia
$95 Chicago, Illinois Cheap Flights from Minneapolis
DealBase.com
$119 Chicago, Illinois $119 & Up: Hilton Chicago O'Hare Airport 4-Star Hotel in Chicago
Expedia
$115 Chicago, Illinois Cheap Flights from Boston
DealBase.com
$190 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Sep: $190 & Up
Expedia
$275 Chicago, Illinois Cheap Flights from Los Angeles
DealBase.com
$166 Chicago, Illinois Book 3.5-Star Central Loop in Chicago Fr $166+/Nt
Expedia
$145 Chicago, Illinois Cheap Flights from Denver
DealBase.com
$141 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $141+/Nt
Save with Expedia, $25/night less
$255 Chicago, Illinois Cheap Flights from Portland
DealBase.com
$383 Chicago, Illinois Book 5-Star Waldorf Astoria Chicago Fr $383+/Nt
Expedia
$115 Chicago, Illinois Cheap Flights from Dallas
DealBase.com
$196 Chicago, Illinois Sep deal: Homewood Suites by Hilton Chicago Downtown Fr $196+/Nt
Expedia
$284 Chicago, Illinois Cheap Flights from Philadelphia
DealBase.com
$236 Chicago, Illinois Book 3.5-Star Renaissance Chicago O'Hare Suites Fr $236+/Nt
Expedia
$328 Chicago, Illinois United Airlines Weekend Specials for 9/19/14
DealBase.com
$238 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $238+/Nt
Save with Expedia, $41/night less
$187 Chicago, Illinois Cheap Flights from St. Louis
DealBase.com
$209 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $209+/Nt
Expedia
$135 Chicago, Illinois Cheap Flights from Orlando
DealBase.com
$230 Chicago, Illinois Special deal: 4-Star Sheraton Chicago and Towers Fr $230+/Nt
Expedia
$173 Chicago, Illinois Cheap Flights from Houston
DealBase.com
$156 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $156+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$152 Chicago, Illinois Book in Chicago: Save at the Days Inn Chicago in Sep Fr $152+/Nt
Expedia
$205 Chicago, Illinois Cheap Flights from Salt Lake City
DealBase.com
$239 Chicago, Illinois Embassy Suites Chicago Downtown in Sep: $239 & Up
Expedia
$328 Chicago, Illinois Cheap Flights from Miami
DealBase.com
$207 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Sep: $207 & Up
Expedia
$251 Chicago, Illinois Cheap Flights from Seattle
DealBase.com
$269 Chicago, Illinois Special deal: 3.5-Star Renaissance Chicago Fr $269+/Nt
Expedia
$165 Chicago, Illinois Cheap Flights from Baltimore
DealBase.com
$198 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $198+/Nt
Save with Expedia, $106/night less
$265 Chicago, Illinois Cheap Flights from San Francisco
DealBase.com
$130 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $130+/Nt
Expedia
$328 Chicago, Illinois United Airlines Weekend Specials for 9/19/14
DealBase.com
$233 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $233+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$179 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $179+/Nt
Expedia
$156 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $156+/Nt
Expedia
$223 Chicago, Illinois Sep deal: Fairmont Chicago Millennium Park Fr $223+/Nt
Save with Expedia, $40/night less
$100 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $100+/Nt
Expedia
$170 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $170+/Nt
Expedia
$229 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $229+/Nt
Expedia
$255 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $255+/Nt
Expedia
$229 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $229+/Nt
Expedia
$428 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $428+/Nt
Save with Expedia, $107/night less
$144 Chicago, Illinois Holiday Inn Chicago O'Hare in Sep: $144 & Up
Expedia
$183 Chicago, Illinois $183 & Up: The Palmer House Hilton 4-Star Hotel in Chicago
Expedia
$189 Chicago, Illinois Book in Chicago: Save this Sep Fr $189+/Nt
Expedia
$173 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $173+/Nt
Expedia
$199 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $199+/Nt
Expedia
$174 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $174+/Nt
Expedia
$178 Chicago, Illinois Holiday Inn Chicago Mart Plaza River North in Sep: $178 & Up
Expedia
$199 Chicago, Illinois Chicago Savings! Book at Hyatt Regency Chicago Fr $199+/Nt
Expedia
$212 Chicago, Illinois ACME Company Chicago on Sale: Book 3 Nts in Sep Fr $212+/Nt
Save with Expedia, $11/night less
$219 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $219+/Nt
Expedia
$196 Chicago, Illinois Book 4-Star Felix Fr $196+/Nt
Save with Expedia, $35/night less
$219 Chicago, Illinois Book 3-Star Comfort Suites Michigan Avenue in Chicago Fr $219+/Nt
Expedia
$229 Chicago, Illinois Sep deal: The Drake Fr $229+/Nt
Expedia
$236 Chicago, Illinois Save at 4-Star W Chicago Lakeshore: $236 & Up in Sep
Expedia
$189 Chicago, Illinois Book 3.5-Star Hyatt Regency McCormick Place Fr $189+/Nt
Expedia
$213 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $213+/Nt
Expedia
$213 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $213+/Nt
Expedia
$208 Chicago, Illinois Save at 4.5-Star Omni Chicago: $208 & Up in Sep
Save with Expedia, $51/night less
$195 Chicago, Illinois Save at 4-Star Millennium Knickerbocker Chicago: $195 & Up in Sep
Save with Expedia, $34/night less
$299 Chicago, Illinois theWit - A DoubleTree by Hilton in Sep: $299 & Up
Expedia
$263 Chicago, Illinois Sep deal: Chicago Downtown, Autograph Collection Fr $263+/Nt
Expedia
$110 Chicago, Illinois BEST WESTERN Grant Park in Sep: $110 & Up
Save with Expedia, $27/night less
$147 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $147+/Nt
Expedia
$233 Chicago, Illinois Kinzie in Sep: $233 & Up
Expedia
$805 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $805
Expedia
$306 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $306+/Nt
Expedia
$259 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $259+/Nt
Expedia
$742 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $742
Expedia
$200 Chicago, Illinois Residence Inn Chicago Downtown / River North in Sep: $200 & Up
Expedia
$392 Chicago, Illinois Special deal: 5-Star Four Seasons Chicago Fr $392+/Nt
Save with Expedia, $43/night less
$139 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $139+/Nt
Expedia
$186 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $186+/Nt
Expedia
$276 Chicago, Illinois Special deal: 4-Star The Blackstone A Renaissance Fr $276+/Nt
Expedia
$310 Chicago, Illinois Special deal: 4-Star Radisson Blu Aqua Fr $310+/Nt
Expedia
$858 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $858
Expedia
$186 Chicago, Illinois Book in Chicago: Save this Sep Fr $186+/Nt
Expedia
PRICEDESTINATIONDEAL
$145 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$308 New York City, New York Cheap Flights from Minneapolis
DealBase.com
$215 New York City, New York Cheap Flights from Dallas
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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