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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$30 Chicago, Illinois Cheap Flights from Washington, DC
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$186 Chicago, Illinois Hampton Inn Chicago Downtown/Magnificent Mile in Sep: $186 & Up
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$172 Chicago, Illinois Chicago Marriott at Medical District/UIC in Sep: $172 & Up
Expedia
$81 Chicago, Illinois Cheap Flights from New York
DealBase.com
$223 Chicago, Illinois Save at 4-Star PUBLIC Chicago: $223 & Up in Sep
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$233 Chicago, Illinois Save at 4.5-Star Radisson Blu Aqua: $233 & Up in Sep
Expedia
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$136 Chicago, Illinois $136 & Up: River 3.5-Star Hotel in Chicago
Expedia
$97 Chicago, Illinois Cheap Flights from Tampa
DealBase.com
$273 Chicago, Illinois Book in Chicago: Save at the The James Chicago in Sep Fr $273+/Nt
Expedia
$59 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$187 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $187+/Nt
Expedia
$80 Chicago, Illinois Cheap Flights from Philadelphia
DealBase.com
$146 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Sep: $146 & Up
Save with Expedia, $25/night less
$99 Chicago, Illinois Cheap Flights from Los Angeles
DealBase.com
$173 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $173+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$229 Chicago, Illinois Sep deal: Comfort Suites Michigan Avenue Fr $229+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
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$163 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $163+/Nt
Expedia
$30 Chicago, Illinois Cheap Flights from Raleigh
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$161 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $161+/Nt
Save with Expedia, $28/night less
$139 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$179 Chicago, Illinois Sep deal: Embassy Suites by Hilton Chicago Downtown Fr $179+/Nt
Expedia
$169 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$159 Chicago, Illinois Special deal: 4-Star Wyndham Grand Chicago Riverfront Fr $159+/Nt
Save with Expedia, $106/night less
$280 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 9/11/15
DealBase.com
$177 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $177+/Nt
Expedia
$100 Chicago, Illinois Cheap Flights from Las Vegas
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$449 Chicago, Illinois Book 5-Star Waldorf Astoria Chicago in Chicago Fr $449+/Nt
Expedia
$200 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$149 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $149+/Nt
Expedia
$87 Chicago, Illinois Cheap Flights from Houston
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$285 Chicago, Illinois Book in Chicago: Save at the Swissotel Chicago in Sep Fr $285+/Nt
Save with Expedia, $31/night less
$177 Chicago, Illinois Cheap Flights from Portland
DealBase.com
$169 Chicago, Illinois Small budget: Book Chicago's Essex Inn 3 Nts in Sep Fr $169+/Nt
Expedia
$81 Chicago, Illinois Cheap Flights from Minneapolis
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$187 Chicago, Illinois Book the Warwick Allerton Chicago 3 Nts in Sep Fr $187+/Nt
Expedia
$261 Chicago, Illinois Alaska Airlines Flight Specials
DealBase.com
$194 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $194+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$169 Chicago, Illinois Save Big This Sep! Book 3 Nts at Blake Chicago Fr $169+/Nt
Expedia
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$197 Chicago, Illinois Special deal: 3-Star BEST WESTERN River North Fr $197+/Nt
Expedia
$200 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$190 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $190+/Nt
Expedia
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$203 Chicago, Illinois Sep deal: Chicago Downtown, Autograph Collection Fr $203+/Nt
Expedia
$169 Chicago, Illinois Alaska Airlines Flight Specials
DealBase.com
$226 Chicago, Illinois Sep deal: Chicago Marriott Downtown Magnificent Mile Fr $226+/Nt
Expedia
$80 Chicago, Illinois Cheap Flights from Denver
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$183 Chicago, Illinois Chicago Savings! Book at Felix Fr $183+/Nt
Save with Expedia, $32/night less
$202 Chicago, Illinois Alaska Airlines Flight Specials
DealBase.com
$185 Chicago, Illinois Sep deal: Courtyard Chicago Downtown/Magnificent Mile Fr $185+/Nt
Expedia
$214 Chicago, Illinois Cheap Flights from Newark
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$189 Chicago, Illinois Special deal: 3-Star Residence Inn Chicago Downtown Fr $189+/Nt
Expedia
$79 Chicago, Illinois Cheap Flights from Baltimore
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$288 Chicago, Illinois Book in Chicago: Save this Sep Fr $288+/Nt
Expedia
$100 Chicago, Illinois Cheap Flights from San Francisco
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$355 Chicago, Illinois Chicago Savings! Book at Park Hyatt Chicago Fr $355+/Nt
Expedia
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$195 Chicago, Illinois Chicago Savings! Book at Hard Rock Chicago Fr $195+/Nt
Save with Expedia, $34/night less
$80 Chicago, Illinois Cheap Flights from Orlando
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$181 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $181+/Nt
Expedia
$268 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 9/11/15
DealBase.com
$159 Chicago, Illinois Hampton Inn & Suites Chicago - Downtown in Sep: $159 & Up
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$161 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $161+/Nt
Save with Expedia, $28/night less
$199 Chicago, Illinois Cheap Flights from St. Louis
DealBase.com
$120 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $120+/Nt
Expedia
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$186 Chicago, Illinois Courtyard Chicago Downtown River North in Sep: $186 & Up
Expedia
$310 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 9/11/15
DealBase.com
$133 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $133+/Nt
Expedia
$81 Chicago, Illinois Cheap Flights from Dallas
DealBase.com
$346 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $346+/Nt
Expedia
$200 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$141 Chicago, Illinois Small budget: Book Central Loop 3 Nts in Sep Fr $141+/Nt
Expedia
$100 Chicago, Illinois Cheap Flights from Salt Lake City
DealBase.com
$172 Chicago, Illinois The Tremont Chicago at Magnificent Mile in Sep: $172 & Up
Expedia
$200 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$213 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $213+/Nt
Expedia
$98 Chicago, Illinois Cheap Flights from Miami
DealBase.com
$110 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $110+/Nt
Save with Expedia, $19/night less
$78 Chicago, Illinois Cheap Flights from Atlanta
DealBase.com
$220 Chicago, Illinois Book in Chicago: Save this Sep Fr $220+/Nt
Expedia
$345 Chicago, Illinois Cheap Flights from Seattle
DealBase.com
$179 Chicago, Illinois Allegro Chicago - a Kimpton in Sep: $179 & Up
Expedia
$81 Chicago, Illinois Cheap Flights from Boston
DealBase.com
$229 Chicago, Illinois Book 4-Star theWit - A DoubleTree by Hilton Fr $229+/Nt
Expedia
$15+ Chicago, Illinois Chicago Vacation Rental Deals From $15
Tripping
$251 Chicago, Illinois Sep deal: Sofitel Chicago Water Tower Fr $251+/Nt
Expedia
$149+ Chicago, Illinois $149: Crowne Plaza Chicago Metro
Hotels.com
$304 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $304+/Nt
Save with Expedia, $151/night less
$129+ Chicago, Illinois $129: Raffaello Hotel, Chicago
Hotels.com
$165 Chicago, Illinois dana and spa in Sep: $165 & Up
Save with Expedia, $41/night less
$178+ Chicago, Illinois $178: The James Chicago
Hotels.com
PRICEDESTINATIONDEAL
$117 Philadelphia, Pennsylvania Cheap Flights from Boston
DealBase.com
$49 Philadelphia, Pennsylvania Frontier Airlines Last Minute Fares
DealBase.com
$78 Philadelphia, Pennsylvania 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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