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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
$156 Chicago, Illinois Book the Holiday Inn Chicago Downtown 3 Nts in Sep Fr $156+/Nt
Expedia
$125 Chicago, Illinois Cheap Flights from Atlanta
DealBase.com
$588 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $588
Expedia
$115 Chicago, Illinois Cheap Flights from Boston
DealBase.com
$146 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport in Chicago Fr $146+/Nt
Expedia
$272 Chicago, Illinois Cheap Flights from Los Angeles
DealBase.com
$159 Chicago, Illinois Book 3.5-Star Hyatt Regency McCormick Place Fr $159+/Nt
Expedia
$251 Chicago, Illinois Cheap Flights from Seattle
DealBase.com
$239 Chicago, Illinois Book 3.5-Star Embassy Suites Chicago Downtown Fr $239+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$243 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $243+/Nt
Save with Expedia, $43/night less
$165 Chicago, Illinois Cheap Flights from Baltimore
DealBase.com
$176 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $176+/Nt
Save with Expedia, $59/night less
$283 Chicago, Illinois Cheap Flights from San Diego
DealBase.com
$176 Chicago, Illinois Book 4-Star Felix in Chicago Fr $176+/Nt
Save with Expedia, $31/night less
$226 Chicago, Illinois Cheap Flights from Newark
DealBase.com
$221 Chicago, Illinois Save at 4-Star Millennium Knickerbocker Chicago: $221 & Up in Sep
Save with Expedia, $38/night less
$99+ Chicago, Illinois Save Up To 25% on 4-Star Chicago Hotels
trivago
$201 Chicago, Illinois $201 & Up: ACME Company Chicago 3-Star Hotel in Chicago
Save with Expedia, $8/night less
$150 Chicago, Illinois Cheap Flights from Orlando
DealBase.com
$279 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $279+/Nt
Expedia
$145 Chicago, Illinois Cheap Flights from Denver
DealBase.com
$269 Chicago, Illinois Save at 3.5-Star Renaissance Chicago: $269 & Up in Sep
Expedia
$227 Chicago, Illinois Cheap Flights from Raleigh
DealBase.com
$178 Chicago, Illinois Sep deal: Holiday Inn Chicago Mart Plaza River North Fr $178+/Nt
Expedia
$265 Chicago, Illinois Cheap Flights from San Francisco
DealBase.com
$269 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $269+/Nt
Expedia
$173 Chicago, Illinois Cheap Flights from Houston
DealBase.com
$226 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $226+/Nt
Expedia
$255 Chicago, Illinois Cheap Flights from Portland
DealBase.com
$229 Chicago, Illinois The Drake on Sale: Book 3 Nts in Sep Fr $229+/Nt
Expedia
$187 Chicago, Illinois Cheap Flights from St. Louis
DealBase.com
$189 Chicago, Illinois Chicago Savings! Book at Chicago's Essex Inn Fr $189+/Nt
Expedia
$195 Chicago, Illinois Cheap Flights from New York
DealBase.com
$362 Chicago, Illinois Book in Chicago: Save this Sep Fr $362+/Nt
Expedia
$293 Chicago, Illinois Cheap Flights from Miami
DealBase.com
$253 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $253+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$649 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $649
Expedia
$115 Chicago, Illinois Cheap Flights from Dallas
DealBase.com
$428 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $428+/Nt
Save with Expedia, $107/night less
$95 Chicago, Illinois Cheap Flights from Minneapolis
DealBase.com
$939 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $939
Expedia
$205 Chicago, Illinois Cheap Flights from Salt Lake City
DealBase.com
$313 Chicago, Illinois Save at 4-Star Radisson Blu Aqua: $313 & Up in Sep
Expedia
$284 Chicago, Illinois Cheap Flights from Philadelphia
DealBase.com
$1,571 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $1,571
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$157 Chicago, Illinois Indigo Chicago Downtown Gold Coast in Sep: $157 & Up
Expedia
$1,219 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,219
Expedia
$164 Chicago, Illinois Sep deal: Club Quarters Chicago - Central Loop Fr $164+/Nt
Expedia
$160 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago at River Fr $160+/Nt
Save with Expedia, $6/night less
$270 Chicago, Illinois Book in Chicago: Save this Sep Fr $270+/Nt
Expedia
$139 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $139+/Nt
Expedia
$259 Chicago, Illinois Book in Chicago: Save this Sep Fr $259+/Nt
Save with Expedia, $64/night less
$189 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $189+/Nt
Expedia
$255 Chicago, Illinois Book 4-Star W Chicago - City Center Fr $255+/Nt
Expedia
$169 Chicago, Illinois Book the Comfort Suites Michigan Avenue 3 Nts in Sep Fr $169+/Nt
Expedia
$296 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $296+/Nt
Expedia
$224 Chicago, Illinois Sep deal: Courtyard Chicago Downtown/Magnificent Mile Fr $224+/Nt
Expedia
$170 Chicago, Illinois Book in Chicago: Save this Sep Fr $170+/Nt
Expedia
$183 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $183+/Nt
Expedia
$840 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $840
Expedia
$166 Chicago, Illinois Book 3.5-Star Central Loop in Chicago Fr $166+/Nt
Expedia
$174 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $174+/Nt
Expedia
$246 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $246+/Nt
Expedia
$838 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $838
Expedia
$232 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep at dana and spa Fr $232+/Nt
Save with Expedia, $41/night less
$103 Chicago, Illinois Sep deal: Hostelling International Chicago Fr $103+/Nt
Expedia
$141 Chicago, Illinois Save at 3-Star Chicago South Loop: $141 & Up in Sep
Save with Expedia, $25/night less
$223 Chicago, Illinois Book 4-Star Fairmont Chicago Millennium Park Fr $223+/Nt
Save with Expedia, $40/night less
$126 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep at Congress Plaza Fr $126+/Nt
Expedia
$223 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $223+/Nt
Expedia
$213 Chicago, Illinois Save Big This Sep! Book 3 Nts in Chicago Fr $213+/Nt
Expedia
$385 Chicago, Illinois Chicago Savings! Book at Four Seasons Chicago Fr $385+/Nt
Expedia
$193 Chicago, Illinois Chicago Savings! Book at Hard Rock Chicago Fr $193+/Nt
Expedia
$209 Chicago, Illinois Save in Chicago: Book 3 Nts in Sep Fr $209+/Nt
Expedia
$884 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $884
Expedia
$208 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $208+/Nt
Save with Expedia, $51/night less
$215 Chicago, Illinois Chicago Marriott at Medical District/UIC in Sep: $215 & Up
Expedia
$156 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $156+/Nt
Expedia
$179 Chicago, Illinois Chicago Savings! Book at Hilton Chicago Fr $179+/Nt
Expedia
$299 Chicago, Illinois Save at 4-Star theWit - A DoubleTree by Hilton: $299 & Up in Sep
Expedia
$161 Chicago, Illinois Allegro Chicago - a Kimpton in Sep: $161 & Up
Save with Expedia, $28/night less
$249 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $249+/Nt
Expedia
$195 Chicago, Illinois $195 & Up: Raffaello 4-Star Hotel in Chicago
Save with Expedia, $104/night less
$130 Chicago, Illinois Book 3-Star The Tremont Chicago at Magnificent Mile Fr $130+/Nt
Expedia
$178 Chicago, Illinois Sep deal: Hampton Inn & Suites Chicago - Downtown Fr $178+/Nt
Expedia
$200 Chicago, Illinois Residence Inn Chicago Downtown / River North in Sep: $200 & Up
Expedia
$191 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $191+/Nt
Expedia
$174 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $174+/Nt
Expedia
$248 Chicago, Illinois $248 & Up: Sofitel Chicago Water Tower 4.5-Star Hotel in Chicago
Expedia
$190 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $190+/Nt
Expedia
$375 Chicago, Illinois Book 5-Star Waldorf Astoria Chicago Fr $375+/Nt
Expedia
$196 Chicago, Illinois La Quinta Inn & Suites Chicago Downtown in Sep: $196 & Up
Expedia
$200 Chicago, Illinois Book in Chicago: Save at the The Whitehall in Sep Fr $200+/Nt
Save with Expedia, $49/night less
$176 Chicago, Illinois Book 3.5-Star Blake Chicago in Chicago Fr $176+/Nt
Expedia
$256 Chicago, Illinois Chicago Savings! Book 3 Nts in Sep Fr $256+/Nt
Expedia
$199 Chicago, Illinois Small budget: Stay in Chicago this Sep Fr $199+/Nt
Expedia
PRICEDESTINATIONDEAL
$145 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$288 New York City, New York Cheap Flights from Salt Lake City
DealBase.com
$235 New York City, New York Cheap Flights from Houston
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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