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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$13 Chicago, Illinois Cheap Car Rentals in Chicago Fr $13/Day
CarRentals.com
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$17 Chicago, Illinois Cheap Car Rentals in Chicago Fr $17/Day
CarRentals.com
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$249 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $249+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$159 Chicago, Illinois Save at 4.5-Star Conrad Chicago: $159 & Up in Oct
Expedia
$280 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$85 Chicago, Illinois Indigo Chicago Downtown Gold Coast in Oct: $85 & Up
Expedia
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$109 Chicago, Illinois Book the Holiday Inn Express Cass 3 Nts in Oct Fr $109+/Nt
Expedia
$270 Chicago, Illinois US Airways Domestic e-Saver Specials for 11/1/14
DealBase.com
$115 Chicago, Illinois Oct deal: theWit - A DoubleTree by Hilton Fr $115+/Nt
Expedia
$228 Chicago, Illinois United Airlines Weekend Specials for 10/31/14
DealBase.com
$112 Chicago, Illinois Oct deal: Radisson Blu Aqua Fr $112+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$149 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $149+/Nt
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$122 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $122+/Nt
Expedia
$133 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$143 Chicago, Illinois Book the Residence Inn Chicago Downtown 3 Nts in Oct Fr $143+/Nt
Expedia
$115 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$86 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $86+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$133 Chicago, Illinois Wyndham Grand Chicago Riverfront in Oct: $133 & Up
Save with Expedia, $23/night less
$53 Chicago, Illinois Spirit Airlines New Orleans Non-Stop Specials
DealBase.com
$127 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $127+/Nt
Save with Expedia, $68/night less
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$68 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Oct: $68 & Up
Save with Expedia, $17/night less
$280 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$149 Chicago, Illinois Oct deal: Kinzie Fr $149+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$99 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $99+/Nt
Expedia
$169 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$97 Chicago, Illinois Oct deal: Hyatt Chicago Magnificent Mile Fr $97+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$85 Chicago, Illinois Book in Chicago: Save this Oct Fr $85+/Nt
Save with Expedia, $14/night less
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$140 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $140+/Nt
Save with Expedia, $59/night less
$162 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$102 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $102+/Nt
Expedia
$310 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$128 Chicago, Illinois Special deal: 4-Star Warwick Allerton Chicago Fr $128+/Nt
Save with Expedia, $60/night less
$268 Chicago, Illinois American Airlines Domestic Getaways for This Weekend - 10/31/14
DealBase.com
$81 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $81+/Nt
Save with Expedia, $8/night less
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$127 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $127+/Nt
Expedia
$134 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$144 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $144+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$140 Chicago, Illinois La Quinta Inn & Suites Chicago Downtown in Oct: $140 & Up
Expedia
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$117 Chicago, Illinois Oct deal: Chicago Downtown, Autograph Collection Fr $117+/Nt
Save with Expedia, $39/night less
$23 Chicago, Illinois Spirit Airlines Winter Survival Sale
DealBase.com
$85 Chicago, Illinois Oct deal: Crowne Plaza Chicago Magnificent Mile Fr $85+/Nt
Expedia
$253 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$151 Chicago, Illinois Book 4.5-Star Sofitel Chicago Water Tower in Chicago Fr $151+/Nt
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 10/31/14
DealBase.com
$119 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $119+/Nt
Expedia
$112 Chicago, Illinois Southwest Airlines Grab Your Favorite Seat Sale
DealBase.com
$119 Chicago, Illinois Special deal: 4-Star MileNorth, A Chicago Fr $119+/Nt
Expedia
$328 Chicago, Illinois United Airlines Weekend Specials for 10/31/14
DealBase.com
$104 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $104+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$161 Chicago, Illinois Chicago Marriott at Medical District/UIC in Oct: $161 & Up
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$128 Chicago, Illinois Book in Chicago: Save this Oct Fr $128+/Nt
Save with Expedia, $32/night less
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$94 Chicago, Illinois $94 & Up: BEST WESTERN River North 3-Star Hotel in Chicago
Expedia
$119 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $119+/Nt
Save with Expedia, $20/night less
$395 Chicago, Illinois Book the Waldorf Astoria Chicago 3 Nts in Oct Fr $395+/Nt
Expedia
$101 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $101+/Nt
Expedia
$107 Chicago, Illinois Oct deal: ACME Company Chicago Fr $107+/Nt
Save with Expedia, $18/night less
$89 Chicago, Illinois Oct deal: Hampton Majestic Chicago Theatre District Fr $89+/Nt
Expedia
$129 Chicago, Illinois Save at 4-Star Hyatt Regency Chicago: $129 & Up in Oct
Expedia
$74 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $74+/Nt
Expedia
$109 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $109+/Nt
Expedia
$126 Chicago, Illinois Oct deal: Buckingham Athletic Club Fr $126+/Nt
Expedia
$93 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $93+/Nt
Expedia
$127 Chicago, Illinois Small budget: Book Burnham - a Kimpton 3 Nts in Oct Fr $127+/Nt
Save with Expedia, $22/night less
$97 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $97+/Nt
Expedia
$95 Chicago, Illinois Book in Chicago: Save this Oct Fr $95+/Nt
Expedia
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $127+/Nt
Expedia
$130 Chicago, Illinois Book the W Chicago Lakeshore 3 Nts in Oct Fr $130+/Nt
Expedia
$139 Chicago, Illinois Book in Chicago: Save this Oct Fr $139+/Nt
Save with Expedia, $25/night less
$72 Chicago, Illinois BEST WESTERN Grant Park in Oct: $72 & Up
Save with Expedia, $18/night less
$96 Chicago, Illinois Book 3.5-Star River Fr $96+/Nt
Save with Expedia, $10/night less
$90 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $90+/Nt
Expedia
$149 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $149+/Nt
Expedia
$139 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport in Chicago Fr $139+/Nt
Expedia
$161 Chicago, Illinois Save Big This Oct! Book 3 Nts at The James Chicago Fr $161+/Nt
Save with Expedia, $28/night less
$159 Chicago, Illinois Book the Renaissance Chicago 3 Nts in Oct Fr $159+/Nt
Expedia
$109 Chicago, Illinois The Westin Michigan Avenue Chicago in Oct: $109 & Up
Expedia
$276 Chicago, Illinois Oct deal: Trump International & Tower Chicago Fr $276+/Nt
Save with Expedia, $69/night less
$102 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Blake Chicago Fr $102+/Nt
Expedia
$350 Chicago, Illinois Chicago Savings! Book at The Peninsula Chicago Fr $350+/Nt
Save with Expedia, $175/night less
$109 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $109+/Nt
Expedia
$144 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $144+/Nt
Save with Expedia, $15/night less
$99 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $99+/Nt
Expedia
$93 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $93+/Nt
Expedia
PRICEDESTINATIONDEAL
$220 Newark, New Jersey Cheap Flights from Charlotte
DealBase.com
$337 Newark, New Jersey Cheap Flights from Los Angeles
DealBase.com
$201 Newark, New Jersey Cheap Flights from Nashville
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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