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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$228 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$39 Chicago, Illinois Frontier Airlines Time to Fly Sale
DealBase.com
$496 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $496
Expedia
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$642 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $642
Expedia
$157 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$14 Chicago, Illinois Cheap Car Rentals in Chicago Fr $14/Day
CarRentals.com
$129 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$375 Chicago, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Chicago Fr $375
Expedia
$164 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$113 Chicago, Illinois The Palmer House Hilton in Oct: $113 & Up
Expedia
$228 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts at Burnham - a Kimpton Fr $127+/Nt
Save with Expedia, $22/night less
$253 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$143 Chicago, Illinois La Quinta Inn & Suites Chicago Downtown in Oct: $143 & Up
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$195 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $195+/Nt
Save with Expedia, $34/night less
$267 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$158 Chicago, Illinois Save at 4-Star The Westin Chicago River North: $158 & Up in Oct
Expedia
$230 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$173 Chicago, Illinois Residence Inn Chicago Downtown in Oct: $173 & Up
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$279 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $279+/Nt
Save with Expedia, $70/night less
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$734 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $734
Expedia
$129 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$136 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $136+/Nt
Save with Expedia, $23/night less
$310 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$136 Chicago, Illinois Book 4-Star Raffaello Fr $136+/Nt
Save with Expedia, $73/night less
$133 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$149 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $149+/Nt
Expedia
$107 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$106 Chicago, Illinois Oct deal: Crowne Plaza Chicago Magnificent Mile Fr $106+/Nt
Expedia
$268 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$159 Chicago, Illinois Book 3.5-Star Buckingham Athletic Club in Chicago Fr $159+/Nt
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$166 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $166+/Nt
Expedia
$110 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$111 Chicago, Illinois Book 3-Star Holiday Inn Chicago Downtown Fr $111+/Nt
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$109 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $109+/Nt
Expedia
$310 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$99 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $99+/Nt
Expedia
$99 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $99+/Nt
Expedia
$115 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $115+/Nt
Expedia
$612 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $612
Expedia
$112 Chicago, Illinois Chicago Savings! Book at River Fr $112+/Nt
Save with Expedia, $7/night less
$1,121 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,121
Expedia
$102 Chicago, Illinois Special deal: 4-Star Millennium Knickerbocker Chicago Fr $102+/Nt
Save with Expedia, $17/night less
$147 Chicago, Illinois Save at 3-Star BEST WESTERN River North: $147 & Up in Oct
Expedia
$179 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Oct: $179 & Up
Expedia
$161 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $161+/Nt
Save with Expedia, $69/night less
$121 Chicago, Illinois Oct deal: The Westin Michigan Avenue Chicago Fr $121+/Nt
Expedia
$1,139 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $1,139
Expedia
$156 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $156+/Nt
Expedia
$173 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $173+/Nt
Expedia
$344 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $344+/Nt
Expedia
$133 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in Oct: $133 & Up
Expedia
$109 Chicago, Illinois Crowne Plaza Chicago - The Metro in Oct: $109 & Up
Expedia
$128 Chicago, Illinois Oct deal: Hilton Suites Chicago/Magnificent Mile Fr $128+/Nt
Expedia
$608 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $608
Expedia
$148 Chicago, Illinois Hampton Inn & Suites Chicago - Downtown in Oct: $148 & Up
Expedia
$733 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $733
Expedia
$137 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $137+/Nt
Expedia
$123 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Oct: $123 & Up
Expedia
$115 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $115+/Nt
Expedia
$68 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $68+/Nt
Expedia
$392 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $392+/Nt
Save with Expedia, $43/night less
$152 Chicago, Illinois Oct deal: Embassy Suites Chicago Downtown Fr $152+/Nt
Expedia
$112 Chicago, Illinois Small budget: Book Radisson Blu Aqua 3 Nts in Oct Fr $112+/Nt
Expedia
$121 Chicago, Illinois Oct deal: Warwick Allerton Chicago Fr $121+/Nt
Save with Expedia, $82/night less
$136 Chicago, Illinois Save Big This Oct! Book 3 Nts at Kinzie Fr $136+/Nt
Expedia
$79 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $79+/Nt
Expedia
$128 Chicago, Illinois Book 4.5-Star Omni Chicago in Chicago Fr $128+/Nt
Save with Expedia, $31/night less
$951 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $951
Expedia
$336 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Oct: $336 & Up
Save with Expedia, $60/night less
$88 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $88+/Nt
Expedia
$144 Chicago, Illinois Book 4-Star Fairmont Chicago Millennium Park Fr $144+/Nt
Save with Expedia, $15/night less
$188 Chicago, Illinois Book the The Blackstone A Renaissance 3 Nts in Oct Fr $188+/Nt
Expedia
$135 Chicago, Illinois Chicago Savings! Book at Congress Plaza Fr $135+/Nt
Expedia
$179 Chicago, Illinois Oct deal: The Drake Fr $179+/Nt
Expedia
$199 Chicago, Illinois Book 4-Star JW Marriott Chicago Fr $199+/Nt
Expedia
$370 Chicago, Illinois The Peninsula Chicago in Oct: $370 & Up
Save with Expedia, $185/night less
$260 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $260+/Nt
Expedia
$94 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $94+/Nt
Save with Expedia, $23/night less
$99 Chicago, Illinois Book in Chicago: Save this Oct Fr $99+/Nt
Expedia
$110 Chicago, Illinois Book 3-Star ACME Company Chicago in Chicago Fr $110+/Nt
Save with Expedia, $19/night less
$106 Chicago, Illinois $106 & Up: Central Loop 3.5-Star Hotel in Chicago
Expedia
$171 Chicago, Illinois Chicago Savings! Book at Swissotel Chicago Fr $171+/Nt
Save with Expedia, $42/night less
$119 Chicago, Illinois Special deal: 4-Star Palomar Chicago, a Kimpton Fr $119+/Nt
Save with Expedia, $20/night less
$115 Chicago, Illinois theWit - A DoubleTree by Hilton in Oct: $115 & Up
Expedia
$96 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $96+/Nt
Expedia
$159 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $159+/Nt
Expedia
$159 Chicago, Illinois Book in Chicago: Save this Oct Fr $159+/Nt
Expedia
$88 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Oct: $88 & Up
Save with Expedia, $22/night less
$161 Chicago, Illinois Chicago Savings! Book at Chicago's Essex Inn Fr $161+/Nt
Save with Expedia, $28/night less
$109 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $109+/Nt
Expedia
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$260 New York City, New York American Airlines Domestic Getaways for This Weekend - 10/24/14
DealBase.com
$212 New York City, New York Cheap Flights from Raleigh
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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