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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
$173 Chicago, Illinois Residence Inn Chicago Downtown in Oct: $173 & Up
Expedia
$39 Chicago, Illinois Frontier Airlines Time to Fly Sale
DealBase.com
$385 Chicago, Illinois Book 5-Star Four Seasons Chicago in Chicago Fr $385+/Nt
Expedia
$253 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$750 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $750
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$133 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $133+/Nt
Save with Expedia, $71/night less
$268 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$188 Chicago, Illinois Book the The Blackstone A Renaissance 3 Nts in Oct Fr $188+/Nt
Expedia
$228 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$1,005 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $1,005
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$114 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $114+/Nt
Expedia
$267 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$167 Chicago, Illinois Book in Chicago: Save at the The James Chicago in Oct Fr $167+/Nt
Save with Expedia, $29/night less
$14 Chicago, Illinois Cheap Car Rentals in Chicago Fr $14/Day
CarRentals.com
$133 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $133+/Nt
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$1,899 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,899
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$127 Chicago, Illinois Save Big This Oct! Book 3 Nts at PUBLIC Chicago Fr $127+/Nt
Save with Expedia, $68/night less
$164 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$109 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $109+/Nt
Expedia
$107 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$144 Chicago, Illinois Chicago Savings! Book at The Silversmith Fr $144+/Nt
Save with Expedia, $25/night less
$157 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$152 Chicago, Illinois Oct deal: Embassy Suites Chicago Downtown Fr $152+/Nt
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 10/24/14
DealBase.com
$183 Chicago, Illinois $183 & Up: Buckingham Athletic Club 3.5-Star Hotel in Chicago
Expedia
$110 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$127 Chicago, Illinois Book 3.5-Star Wyndham Grand Chicago Riverfront Fr $127+/Nt
Save with Expedia, $22/night less
$310 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$112 Chicago, Illinois Small budget: Book Radisson Blu Aqua 3 Nts in Oct Fr $112+/Nt
Expedia
$310 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$192 Chicago, Illinois Book 4.5-Star Omni Chicago Fr $192+/Nt
Save with Expedia, $47/night less
$133 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$161 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $161+/Nt
Save with Expedia, $69/night less
$129 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$116 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $116+/Nt
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$140 Chicago, Illinois Residence Inn Chicago Downtown / River North in Oct: $140 & Up
Expedia
$197 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$203 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $203+/Nt
Expedia
$129 Chicago, Illinois Southwest Airlines Cozy Up to Winter Deals
DealBase.com
$561 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $561
Expedia
$230 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 10/31/14
DealBase.com
$166 Chicago, Illinois Book in Chicago: Save this Oct Fr $166+/Nt
Expedia
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$103 Chicago, Illinois Hostelling International Chicago in Oct: $103 & Up
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$136 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Oct: $136 & Up
Expedia
$143 Chicago, Illinois La Quinta Inn & Suites Chicago Downtown in Oct: $143 & Up
Expedia
$115 Chicago, Illinois theWit - A DoubleTree by Hilton in Oct: $115 & Up
Expedia
$260 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $260+/Nt
Expedia
$88 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $88+/Nt
Expedia
$171 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $171+/Nt
Expedia
$136 Chicago, Illinois Save Big This Oct! Book 3 Nts at Kinzie Fr $136+/Nt
Expedia
$119 Chicago, Illinois $119 & Up: W Chicago Lakeshore 4-Star Hotel in Chicago
Expedia
$96 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $96+/Nt
Expedia
$159 Chicago, Illinois Chicago Savings! Book at The Drake Fr $159+/Nt
Expedia
$129 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $129+/Nt
Expedia
$99 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $99+/Nt
Expedia
$159 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $159+/Nt
Expedia
$136 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $136+/Nt
Save with Expedia, $23/night less
$664 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $664
Expedia
$106 Chicago, Illinois Oct deal: Crowne Plaza Chicago Magnificent Mile Fr $106+/Nt
Expedia
$127 Chicago, Illinois Book in Chicago: Save this Oct Fr $127+/Nt
Expedia
$150 Chicago, Illinois Oct deal: Fairmont Chicago Millennium Park Fr $150+/Nt
Save with Expedia, $16/night less
$99 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $99+/Nt
Expedia
$96 Chicago, Illinois Book the The Whitehall 3 Nts in Oct Fr $96+/Nt
Save with Expedia, $23/night less
$930 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $930
Expedia
$159 Chicago, Illinois Book in Chicago: Save this Oct Fr $159+/Nt
Expedia
$169 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $169+/Nt
Expedia
$93 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $93+/Nt
Expedia
$115 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $115+/Nt
Expedia
$94 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $94+/Nt
Expedia
$203 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $203+/Nt
Expedia
$292 Chicago, Illinois Trump International & Tower Chicago in Oct: $292 & Up
Save with Expedia, $73/night less
$126 Chicago, Illinois Book 3-Star Congress Plaza in Chicago Fr $126+/Nt
Expedia
$198 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $198+/Nt
Expedia
$119 Chicago, Illinois Special deal: 4-Star Palomar Chicago, a Kimpton Fr $119+/Nt
Save with Expedia, $20/night less
$129 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $129+/Nt
Expedia
$370 Chicago, Illinois The Peninsula Chicago in Oct: $370 & Up
Save with Expedia, $185/night less
$84 Chicago, Illinois Book 3.5-Star River Fr $84+/Nt
Save with Expedia, $9/night less
$123 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $123+/Nt
Expedia
$127 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $127+/Nt
Expedia
$116 Chicago, Illinois Oct deal: Chicago Marriott at Medical District/UIC Fr $116+/Nt
Expedia
$328 Chicago, Illinois Book 5-Star Waldorf Astoria Chicago in Chicago Fr $328+/Nt
Expedia
$115 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $115+/Nt
Expedia
$94 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $94+/Nt
Save with Expedia, $23/night less
$844 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $844
Expedia
$121 Chicago, Illinois Oct deal: The Westin Michigan Avenue Chicago Fr $121+/Nt
Expedia
$96 Chicago, Illinois Book in Chicago: Save at the Central Loop in Oct Fr $96+/Nt
Expedia
$124 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $124+/Nt
Expedia
$133 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $133+/Nt
Save with Expedia, $6/night less
$197 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $197+/Nt
Expedia
$129 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $129+/Nt
Expedia
$159 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $159+/Nt
Expedia
$149 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $149+/Nt
Expedia
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$217 New York City, New York Cheap Flights from St. Louis
DealBase.com
$185 New York City, New York Cheap Flights from Miami
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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