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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
DealBase.com
$161 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $161+/Nt
Save with Expedia, $28/night less
$138+ Chicago, Illinois $138: dana hotel and spa, Chicago
Priceline.com
$346 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $346+/Nt
Expedia
$280 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 9/11/15
DealBase.com
$896 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $896
Expedia
$99 Chicago, Illinois Cheap Flights from Los Angeles
DealBase.com
$866 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $866
Expedia
$100 Chicago, Illinois Cheap Flights from Las Vegas
DealBase.com
$141 Chicago, Illinois Small budget: Book Central Loop 3 Nts in Sep Fr $141+/Nt
Expedia
$200 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$1,158 Chicago, Illinois Save at 5-Star Hotel: 3 Nts + Air to Chicago Fr $1,158
Expedia
$153+ Chicago, Illinois $153: Chicago Marriott Midway
Priceline.com
$172 Chicago, Illinois The Tremont Chicago at Magnificent Mile in Sep: $172 & Up
Expedia
$87 Chicago, Illinois Cheap Flights from Houston
DealBase.com
$902 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $902
Expedia
$145+ Chicago, Illinois $145: PUBLIC Chicago
Priceline.com
$186 Chicago, Illinois Hampton Inn Chicago Downtown/Magnificent Mile in Sep: $186 & Up
Expedia
$177 Chicago, Illinois Cheap Flights from Portland
DealBase.com
$213 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $213+/Nt
Expedia
$81 Chicago, Illinois Cheap Flights from Minneapolis
DealBase.com
$694 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $694
Expedia
$139 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$1,024 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,024
Expedia
$59 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$172 Chicago, Illinois Chicago Marriott at Medical District/UIC in Sep: $172 & Up
Expedia
$129+ Chicago, Illinois $129: Raffaello Hotel, Chicago
Hotels.com
$110 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $110+/Nt
Save with Expedia, $19/night less
$261 Chicago, Illinois Alaska Airlines Flight Specials
DealBase.com
$1,137 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,137
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
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
$220 Chicago, Illinois Book in Chicago: Save this Sep Fr $220+/Nt
Expedia
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$223 Chicago, Illinois Save at 4-Star PUBLIC Chicago: $223 & Up in Sep
Expedia
$39 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
$80 Chicago, Illinois Cheap Flights from Philadelphia
DealBase.com
$179 Chicago, Illinois Allegro Chicago - a Kimpton in Sep: $179 & Up
Expedia
$200 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$229 Chicago, Illinois Book 4-Star theWit - A DoubleTree by Hilton Fr $229+/Nt
Expedia
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$136 Chicago, Illinois $136 & Up: River 3.5-Star Hotel in Chicago
Expedia
$149+ Chicago, Illinois $149: Crowne Plaza Chicago Metro
Hotels.com
$273 Chicago, Illinois Book in Chicago: Save at the The James Chicago in Sep Fr $273+/Nt
Expedia
$169 Chicago, Illinois Alaska Airlines Flight Specials
DealBase.com
$187 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $187+/Nt
Expedia
$80 Chicago, Illinois Cheap Flights from Denver
DealBase.com
$251 Chicago, Illinois Sep deal: Sofitel Chicago Water Tower Fr $251+/Nt
Expedia
$202 Chicago, Illinois Alaska Airlines Flight Specials
DealBase.com
$304 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $304+/Nt
Save with Expedia, $151/night less
$119+ Chicago, Illinois $119: The Palmer House Hilton, Chicago
Priceline.com
$146 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Sep: $146 & Up
Save with Expedia, $25/night less
$214 Chicago, Illinois Cheap Flights from Newark
DealBase.com
$173 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $173+/Nt
Expedia
$79 Chicago, Illinois Cheap Flights from Baltimore
DealBase.com
$165 Chicago, Illinois dana and spa in Sep: $165 & Up
Save with Expedia, $41/night less
$92+ Chicago, Illinois $92: ACME Hotel Company Chicago
Priceline.com
$150 Chicago, Illinois Book in Chicago: Save this Sep Fr $150+/Nt
Expedia
$103+ Chicago, Illinois $103: Chicago South Loop Hotel
Priceline.com
$169 Chicago, Illinois Book in Chicago: Save this Sep Fr $169+/Nt
Expedia
$100 Chicago, Illinois Cheap Flights from San Francisco
DealBase.com
$229 Chicago, Illinois Sep deal: Comfort Suites Michigan Avenue Fr $229+/Nt
Expedia
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$282 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $282+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$163 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $163+/Nt
Expedia
$80 Chicago, Illinois Cheap Flights from Orlando
DealBase.com
$759 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $759
Expedia
$178+ Chicago, Illinois $178: The James Chicago
Hotels.com
$199 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $199+/Nt
Expedia
$152+ Chicago, Illinois $152: Hotel Monaco Chicago, a Kimpton Hotel
Priceline.com
$161 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $161+/Nt
Save with Expedia, $28/night less
$268 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 9/11/15
DealBase.com
$123 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $123+/Nt
Expedia
$135+ Chicago, Illinois $135: The Westin Chicago River North
Priceline.com
$117 Chicago, Illinois Hostelling International Chicago in Sep: $117 & Up
Expedia
$101+ Chicago, Illinois $101: Millennium Knickerbocker, Chicago
Priceline.com
$179 Chicago, Illinois Sep deal: Embassy Suites by Hilton Chicago Downtown Fr $179+/Nt
Expedia
$181+ Chicago, Illinois $181: Hotel Burnham, a Kimpton Hotel, Chicago
Priceline.com
$149 Chicago, Illinois Sep deal: Holiday Inn Chicago Downtown Fr $149+/Nt
Expedia
$147+ Chicago, Illinois $147: Hotel Palomar Chicago, a Kimpton Hotel
Priceline.com
$159 Chicago, Illinois Special deal: 4-Star Wyndham Grand Chicago Riverfront Fr $159+/Nt
Save with Expedia, $106/night less
$15+ Chicago, Illinois Chicago Vacation Rental Deals From $15
Tripping
$180 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $180+/Nt
Expedia
$89+ Chicago, Illinois $89: Hampton Inn Chicago Downtown/Magnificent Mile
Priceline.com
$1,274 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,274
Expedia
$134+ Chicago, Illinois $134: Congress Plaza Hotel, Chicago
Priceline.com
$960 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $960
Expedia
$141+ Chicago, Illinois $141: Hard Rock Hotel Chicago
Priceline.com
$243 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $243+/Nt
Expedia
$395+ Chicago, Illinois $395: The Langham Chicago
Priceline.com
$177 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $177+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$199 Chicago, Illinois Book the The Drake 3 Nts in Sep Fr $199+/Nt
Expedia
$105+ Chicago, Illinois $105: The Palmer House Hilton, Chicago
Priceline.com
$179 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $179+/Nt
Expedia
$111+ Chicago, Illinois $111: Chicago's Essex Inn
Priceline.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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