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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
$113 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$99+ Chicago, Illinois Save Up To 25% on 4-Star Chicago Hotels
trivago
$135 Chicago, Illinois Cheap Flights from Denver
DealBase.com
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$123 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$89 Chicago, Illinois Sun Country Airlines Fall Fare Sale
DealBase.com
$293 Chicago, Illinois Sep deal: The Westin Chicago River North Fr $293+/Nt
Expedia
$173 Chicago, Illinois Cheap Flights from Houston
DealBase.com
$229 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $229+/Nt
Expedia
$95 Chicago, Illinois Cheap Flights from Minneapolis
DealBase.com
$159 Chicago, Illinois Book in Chicago: Save this Sep Fr $159+/Nt
Expedia
$195 Chicago, Illinois Cheap Flights from New York
DealBase.com
$405 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $405+/Nt
Expedia
$155 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$385 Chicago, Illinois Book in Chicago: Save this Sep Fr $385+/Nt
Expedia
$129 Chicago, Illinois Southwest Airlines Atlanta Specials
DealBase.com
$244 Chicago, Illinois W Chicago Lakeshore on Sale: Book 3 Nts in Sep Fr $244+/Nt
Expedia
$235 Chicago, Illinois Cheap Flights from Portland
DealBase.com
$180 Chicago, Illinois Sep deal: Homewood Suites by Hilton Chicago Downtown Fr $180+/Nt
Expedia
$226 Chicago, Illinois Cheap Flights from Newark
DealBase.com
$259 Chicago, Illinois Book 4-Star Swissotel Chicago in Chicago Fr $259+/Nt
Save with Expedia, $64/night less
$290 Chicago, Illinois Cheap Flights from Seattle
DealBase.com
$243 Chicago, Illinois Sep deal: The Westin Michigan Avenue Chicago Fr $243+/Nt
Expedia
$127 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$269 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $269+/Nt
Expedia
$275 Chicago, Illinois Cheap Flights from Los Angeles
DealBase.com
$132 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $132+/Nt
Expedia
$133 Chicago, Illinois Southwest Airlines Nationwide Sale
DealBase.com
$753 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $753
Expedia
$209 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$161 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $161+/Nt
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$296 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $296+/Nt
Expedia
$225 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$535 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $535
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$727 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $727
Expedia
$133 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$394 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $394+/Nt
Save with Expedia, $98/night less
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$160 Chicago, Illinois Small budget: Book Central Loop 3 Nts in Sep Fr $160+/Nt
Save with Expedia, $6/night less
$265 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$169 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $169+/Nt
Expedia
$155 Chicago, Illinois Cheap Flights from New Orleans
DealBase.com
$208 Chicago, Illinois Omni Chicago on Sale: Book 3 Nts in Sep Fr $208+/Nt
Save with Expedia, $51/night less
$98 Chicago, Illinois Cheap Flights from Salt Lake City
DealBase.com
$129 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $129+/Nt
Expedia
$255 Chicago, Illinois Cheap Flights from San Francisco
DealBase.com
$483 Chicago, Illinois $483 & Up: The Peninsula Chicago 5-Star Hotel in Chicago
Expedia
$247 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$189 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep at Felix Fr $189+/Nt
Save with Expedia, $34/night less
$320 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/3/14
DealBase.com
$127 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $127+/Nt
Save with Expedia, $32/night less
$135 Chicago, Illinois Cheap Flights from Boston
DealBase.com
$189 Chicago, Illinois $189 & Up: Allegro Chicago - a Kimpton 4-Star Hotel in Chicago
Expedia
$287 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$140 Chicago, Illinois Days Inn Chicago on Sale: Book 3 Nts in Sep Fr $140+/Nt
Expedia
$337 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$183 Chicago, Illinois Small budget: Book ACME Company Chicago 3 Nts in Sep Fr $183+/Nt
Save with Expedia, $10/night less
$42 Chicago, Illinois Frontier Airlines $49 Sale
DealBase.com
$176 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $176+/Nt
Expedia
$187 Chicago, Illinois Cheap Flights from St. Louis
DealBase.com
$127 Chicago, Illinois Sep deal: The Tremont Chicago at Magnificent Mile Fr $127+/Nt
Expedia
$339 Chicago, Illinois Cheap Flights from Miami
DealBase.com
$207 Chicago, Illinois Sep deal: Courtyard Chicago Downtown/Magnificent Mile Fr $207+/Nt
Expedia
$15 Chicago, Illinois Frontier Airlines Today Only Sale
DealBase.com
$178 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $178+/Nt
Expedia
$226 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $226+/Nt
Expedia
$175 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $175+/Nt
Save with Expedia, $31/night less
$1,325 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,325
Expedia
$792 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $792
Expedia
$259 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $259+/Nt
Expedia
$236 Chicago, Illinois Save at 4-Star dana and spa: $236 & Up in Sep
Expedia
$383 Chicago, Illinois Sep deal: Waldorf Astoria Chicago Fr $383+/Nt
Expedia
$1,792 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,792
Expedia
$353 Chicago, Illinois Park Hyatt Chicago on Sale: Book 3 Nts in Sep Fr $353+/Nt
Expedia
$173 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $173+/Nt
Save with Expedia, $93/night less
$141 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $141+/Nt
Expedia
$184 Chicago, Illinois Book 3-Star BEST WESTERN River North in Chicago Fr $184+/Nt
Expedia
$196 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $196+/Nt
Expedia
$284 Chicago, Illinois Book in Chicago: Save this Sep Fr $284+/Nt
Expedia
$199 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $199+/Nt
Expedia
$179 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $179+/Nt
Expedia
$195 Chicago, Illinois Book 4.5-Star The James Chicago in Chicago Fr $195+/Nt
Save with Expedia, $64/night less
$199 Chicago, Illinois Book in Chicago: Save this Sep Fr $199+/Nt
Expedia
$215 Chicago, Illinois Sep deal: Chicago Marriott at Medical District/UIC Fr $215+/Nt
Expedia
$203 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $203+/Nt
Expedia
$173 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $173+/Nt
Expedia
$150 Chicago, Illinois Sep deal: Indigo Chicago Downtown Gold Coast Fr $150+/Nt
Expedia
$134 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $134+/Nt
Save with Expedia, $33/night less
$103 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $103+/Nt
Expedia
$157 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $157+/Nt
Expedia
$170 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $170+/Nt
Expedia
$213 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $213+/Nt
Expedia
$242 Chicago, Illinois Sep deal: Sheraton Chicago and Towers Fr $242+/Nt
Expedia
$745 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $745
Expedia
$186 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $186+/Nt
Expedia
$224 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $224+/Nt
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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