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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$76 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in Dec: $76 & Up
Expedia
$31 Chicago, Illinois Chicago Vacation Rental Deals From $31
Tripping
$76 Chicago, Illinois Hampton Inn & Suites Chicago - Downtown in Dec: $76 & Up
Expedia
$106 Chicago, Illinois Ray's Bucktown Bed and Breakfast
Groupon Inc
$146 Chicago, Illinois $146 & Up: PUBLIC Chicago 4-Star Hotel in Chicago
Expedia
$117 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$128 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $128+/Nt
Expedia
$135 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$60 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Dec: $60 & Up
Save with Expedia, $15/night less
$90 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$67 Chicago, Illinois Save in Chicago: Book 3 Nts in Dec Fr $67+/Nt
Save with Expedia, $22/night less
$113 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$99 Chicago, Illinois Book the Embassy Suites Chicago Downtown 3 Nts in Dec Fr $99+/Nt
Expedia
$164 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$83 Chicago, Illinois Chicago Savings! Book at Hyatt Regency McCormick Place Fr $83+/Nt
Expedia
$133 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$125 Chicago, Illinois Kinzie in Dec: $125 & Up
Expedia
$114 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$104 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $104+/Nt
Save with Expedia, $69/night less
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$109 Chicago, Illinois Book the Sheraton Chicago and Towers 3 Nts in Dec Fr $109+/Nt
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$76 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Dec: $76 & Up
Expedia
$140 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$114 Chicago, Illinois Chicago Savings! Book at Radisson Blu Aqua Fr $114+/Nt
Expedia
$241 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$129 Chicago, Illinois Special deal: 4-Star dana and spa Fr $129+/Nt
Expedia
$271 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$97 Chicago, Illinois Special deal: 4-Star Hilton Chicago Fr $97+/Nt
Expedia
$279 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$79 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $79+/Nt
Expedia
$291 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$96 Chicago, Illinois Book 3-Star Comfort Suites Michigan Avenue in Chicago Fr $96+/Nt
Expedia
$239 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$78 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $78+/Nt
Expedia
$225 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$99 Chicago, Illinois InterContinental Chicago on Sale: Book 3 Nts in Dec Fr $99+/Nt
Expedia
$275 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$64 Chicago, Illinois Save in Chicago: Book 3 Nts in Dec Fr $64+/Nt
Save with Expedia, $31/night less
$213 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$93 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $93+/Nt
Expedia
$112 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$75 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $75+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$68 Chicago, Illinois The Tremont Chicago at Magnificent Mile in Dec: $68 & Up
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$119 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $119+/Nt
Expedia
$169 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$81 Chicago, Illinois Book the River 3 Nts in Dec Fr $81+/Nt
Save with Expedia, $8/night less
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$79 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $79+/Nt
Save with Expedia, $14/night less
$153 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$264 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $264+/Nt
Save with Expedia, $131/night less
$126 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$123 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $123+/Nt
Save with Expedia, $13/night less
$179 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$159 Chicago, Illinois Book 3.5-Star Renaissance Chicago in Chicago Fr $159+/Nt
Expedia
$398+ Chicago, Illinois $398+: JW Marriott Chicago Couples' Getaway
JW Marriott Chicago
$179 Chicago, Illinois JW Marriott Chicago in Dec: $179 & Up
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$126 Chicago, Illinois Book 4.5-Star Omni Chicago in Chicago Fr $126+/Nt
Save with Expedia, $13/night less
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$89 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $89+/Nt
Expedia
$212+ Chicago, Illinois $212: Fairmont Chicago at Millennium Park
Hotels.com
$124 Chicago, Illinois Save at 4-Star The Blackstone A Renaissance: $124 & Up in Dec
Expedia
$103+ Chicago, Illinois $103: Millennium Knickerbocker, Chicago
Hotels.com
$99 Chicago, Illinois Book in Chicago: Save this Dec Fr $99+/Nt
Expedia
$188+ Chicago, Illinois $188: The James Chicago
Hotels.com
$86 Chicago, Illinois Save at 4-Star Hilton Chicago O'Hare Airport: $86 & Up in Dec
Expedia
$129+ Chicago, Illinois $129: Raffaello Hotel, Chicago
Hotels.com
$97 Chicago, Illinois BEST WESTERN River North in Dec: $97 & Up
Expedia
$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
Priceline.com
$59 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $59+/Nt
Expedia
$135+ Chicago, Illinois $135: Conrad Chicago
Priceline.com
$112 Chicago, Illinois Book the W Chicago - City Center 3 Nts in Dec Fr $112+/Nt
Expedia
$126+ Chicago, Illinois $126: Kinzie Hotel, Chicago
Priceline.com
$79 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $79+/Nt
Expedia
$158+ Chicago, Illinois $158: dana hotel and spa, Chicago
Priceline.com
$79 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $79+/Nt
Expedia
$132+ Chicago, Illinois $132: SpringHill Suites Chicago O'Hare by Marriott
Priceline.com
$90 Chicago, Illinois Hampton Majestic Chicago Theatre District in Dec: $90 & Up
Expedia
$125+ Chicago, Illinois $125: Embassy Suites Chicago Downtown
Priceline.com
$78 Chicago, Illinois Indigo Chicago Downtown Gold Coast in Dec: $78 & Up
Expedia
$79+ Chicago, Illinois $79: Best Western Grant Park, Chicago
Priceline.com
$117 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $117+/Nt
Expedia
$139+ Chicago, Illinois $139: ACME Hotel Company Chicago
Priceline.com
$88 Chicago, Illinois Millennium Knickerbocker Chicago in Dec: $88 & Up
Expedia
$267+ Chicago, Illinois $267: The Peninsula Chicago
Priceline.com
$294 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $294+/Nt
Expedia
$169+ Chicago, Illinois $169: The Westin Chicago River North
Priceline.com
$119 Chicago, Illinois Dec deal: Buckingham Athletic Club Fr $119+/Nt
Save with Expedia, $20/night less
$175+ Chicago, Illinois $175: PUBLIC Chicago
Priceline.com
$126 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $126+/Nt
Save with Expedia, $13/night less
$179+ Chicago, Illinois $179: Embassy Suites Chicago Downtown - Lakefront
Priceline.com
$116 Chicago, Illinois Chicago Marriott at Medical District/UIC in Dec: $116 & Up
Expedia
$176+ Chicago, Illinois $176: Radisson Blu Aqua Hotel Chicago
Priceline.com
$96 Chicago, Illinois Dec deal: Congress Plaza Fr $96+/Nt
Expedia
$89 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Dec: $89 & Up
Expedia
$109 Chicago, Illinois Book the Residence Inn Chicago Downtown 3 Nts in Dec Fr $109+/Nt
Expedia
PRICEDESTINATIONDEAL
$117 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$197 New York City, New York Cheap Flights from Orlando
DealBase.com
$283 New York City, New York Cheap Flights from San Francisco
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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