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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
$14 Chicago, Illinois Cheap Car Rentals in Chicago Fr $14/Day
CarRentals.com
$253 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$313 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $313+/Nt
Save with Expedia, $78/night less
$93 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$140 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $140+/Nt
Expedia
$228 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
$39 Chicago, Illinois Frontier Airlines Time to Fly Sale
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$173 Chicago, Illinois Oct deal: Residence Inn Chicago Downtown Fr $173+/Nt
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$158 Chicago, Illinois The Westin Chicago River North in Oct: $158 & Up
Expedia
$164 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$136 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $136+/Nt
Save with Expedia, $23/night less
$113 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$136 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $136+/Nt
Save with Expedia, $73/night less
$43 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$106 Chicago, Illinois Book in Chicago: Save this Oct Fr $106+/Nt
Expedia
$68 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$159 Chicago, Illinois Chicago Savings! Book at Buckingham Athletic Club Fr $159+/Nt
Expedia
$267 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$111 Chicago, Illinois Oct deal: Holiday Inn Chicago Downtown Fr $111+/Nt
Expedia
$157 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$167 Chicago, Illinois Holiday Inn Chicago Mart Plaza River North in Oct: $167 & Up
Expedia
$230 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$99 Chicago, Illinois Chicago Savings! Book at Blake Chicago Fr $99+/Nt
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$99 Chicago, Illinois Oct deal: Chicago South Loop Fr $99+/Nt
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$112 Chicago, Illinois Save Big This Oct! Book 3 Nts at River Fr $112+/Nt
Save with Expedia, $7/night less
$129 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$102 Chicago, Illinois Special deal: 4-Star Millennium Knickerbocker Chicago Fr $102+/Nt
Save with Expedia, $17/night less
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
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$176 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $176+/Nt
Expedia
$310 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$161 Chicago, Illinois Monaco Chicago - a Kimpton in Oct: $161 & Up
Save with Expedia, $69/night less
$73 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$161 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $161+/Nt
Expedia
$43 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$179 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $179+/Nt
Expedia
$133 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$121 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $121+/Nt
Expedia
$53 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$143 Chicago, Illinois La Quinta Inn & Suites Chicago Downtown in Oct: $143 & Up
Expedia
$107 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$156 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $156+/Nt
Expedia
$93 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$133 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $133+/Nt
Expedia
$268 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$113 Chicago, Illinois Book in Chicago: Save this Oct Fr $113+/Nt
Expedia
$58 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$344 Chicago, Illinois $344 & Up: Waldorf Astoria Chicago 5-Star Hotel in Chicago
Expedia
$129 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$109 Chicago, Illinois Crowne Plaza Chicago - The Metro in Oct: $109 & Up
Expedia
$278 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
$43 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$159 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $159+/Nt
Expedia
$53 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$148 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $148+/Nt
Expedia
$63 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$209 Chicago, Illinois Chicago Savings! Book at Conrad Chicago Fr $209+/Nt
Expedia
$110 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$68 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $68+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
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$123 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Oct: $123 & Up
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$149 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $149+/Nt
Expedia
$58 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$115 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $115+/Nt
Expedia
$53 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$392 Chicago, Illinois Special deal: 5-Star Four Seasons Chicago Fr $392+/Nt
Save with Expedia, $43/night less
$73 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$161 Chicago, Illinois Book in Chicago: Save this Oct Fr $161+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$152 Chicago, Illinois Book 3.5-Star Embassy Suites Chicago Downtown Fr $152+/Nt
Expedia
$310 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$100 Chicago, Illinois Book in Chicago: Save this Oct Fr $100+/Nt
Expedia
$83 Chicago, Illinois Spirit Airlines $9 Fare Club Fares
DealBase.com
$79 Chicago, Illinois $79 & Up: Holiday Inn Express Cass 3-Star Hotel in Chicago
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$128 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $128+/Nt
Save with Expedia, $31/night less
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$156 Chicago, Illinois Oct deal: Embassy Suites Chicago Downtown Lakefront Fr $156+/Nt
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$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 Chicago Savings! Book at The Blackstone A Renaissance Fr $188+/Nt
Expedia
$135 Chicago, Illinois Chicago Savings! Book at Congress Plaza Fr $135+/Nt
Expedia
$179 Chicago, Illinois Book the The Drake 3 Nts in Oct Fr $179+/Nt
Expedia
$370 Chicago, Illinois The Peninsula Chicago on Sale: Book 3 Nts in Oct Fr $370+/Nt
Save with Expedia, $185/night less
$260 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $260+/Nt
Expedia
$127 Chicago, Illinois Oct deal: Burnham - a Kimpton Fr $127+/Nt
Save with Expedia, $22/night less
$135 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $135+/Nt
Expedia
$124 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $124+/Nt
Expedia
$99 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $99+/Nt
Expedia
$110 Chicago, Illinois Book 3-Star ACME Company Chicago Fr $110+/Nt
Save with Expedia, $19/night less
$179 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $179+/Nt
Expedia
$138 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $138+/Nt
Save with Expedia, $65/night less
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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