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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$140 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$93 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $93+/Nt
Expedia
$153 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$146 Chicago, Illinois Chicago Savings! Book at PUBLIC Chicago Fr $146+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$126+ Chicago, Illinois $126: Kinzie Hotel, Chicago
Priceline.com
$169 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$102 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $102+/Nt
Expedia
$135 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$68 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $68+/Nt
Save with Expedia, $11/night less
$225 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$179+ Chicago, Illinois $179: Embassy Suites Chicago Downtown - Lakefront
Priceline.com
$279 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$82 Chicago, Illinois $82 & Up: The Whitehall 4-Star Hotel in Chicago
Save with Expedia, $14/night less
$164 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$79 Chicago, Illinois Book 3-Star Holiday Inn Chicago Downtown Fr $79+/Nt
Expedia
$275 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$81 Chicago, Illinois Dec deal: Central Loop Fr $81+/Nt
Save with Expedia, $8/night less
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$85 Chicago, Illinois Chicago Savings! Book at Hilton Chicago Fr $85+/Nt
Expedia
$179 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$79 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $79+/Nt
Expedia
$113 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$129 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $129+/Nt
Expedia
$126 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$271 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$76 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $76+/Nt
Expedia
$291 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$126 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $126+/Nt
Save with Expedia, $13/night less
$239 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$76 Chicago, Illinois Dec deal: Travelodge Chicago Downtown Fr $76+/Nt
Expedia
$90 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$119 Chicago, Illinois Book 3.5-Star Buckingham Athletic Club in Chicago Fr $119+/Nt
Save with Expedia, $20/night less
$133 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$129 Chicago, Illinois Small budget: Book dana and spa 3 Nts in Dec Fr $129+/Nt
Expedia
$112 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$102 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $102+/Nt
Expedia
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$109 Chicago, Illinois Dec deal: Sheraton Chicago and Towers Fr $109+/Nt
Expedia
$213 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$79 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $79+/Nt
Expedia
$241 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$109 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $109+/Nt
Expedia
$114 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$96 Chicago, Illinois Dec deal: Comfort Suites Michigan Avenue Fr $96+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$75 Chicago, Illinois Save Big This Dec! Book 3 Nts in Chicago Fr $75+/Nt
Expedia
$117 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$80 Chicago, Illinois Small budget: Book Hyatt Regency Chicago 3 Nts in Dec Fr $80+/Nt
Save with Expedia, $19/night less
$135+ Chicago, Illinois $135: Conrad Chicago
Priceline.com
$89 Chicago, Illinois Book in Chicago: Save this Dec Fr $89+/Nt
Expedia
$129+ Chicago, Illinois $129: Raffaello Hotel, Chicago
Hotels.com
$126 Chicago, Illinois Palomar Chicago, a Kimpton on Sale: Book 3 Nts in Dec Fr $126+/Nt
Save with Expedia, $13/night less
$31 Chicago, Illinois Chicago Vacation Rental Deals From $31
Tripping
$100 Chicago, Illinois Save Big This Dec! Book 3 Nts in Chicago Fr $100+/Nt
Expedia
$175+ Chicago, Illinois $175: PUBLIC Chicago
Priceline.com
$92 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $92+/Nt
Expedia
$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
Priceline.com
$81 Chicago, Illinois Club Quarters Chicago - Central Loop in Dec: $81 & Up
Save with Expedia, $8/night less
$212+ Chicago, Illinois $212: Fairmont Chicago at Millennium Park
Hotels.com
$128 Chicago, Illinois The Westin Chicago River North in Dec: $128 & Up
Expedia
$132+ Chicago, Illinois $132: SpringHill Suites Chicago O'Hare by Marriott
Priceline.com
$60 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Dec: $60 & Up
Save with Expedia, $15/night less
$158+ Chicago, Illinois $158: dana hotel and spa, Chicago
Priceline.com
$99 Chicago, Illinois Book in Chicago: Save at the Chicago South Loop in Dec Fr $99+/Nt
Expedia
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$109 Chicago, Illinois Book 4-Star theWit - A DoubleTree by Hilton Fr $109+/Nt
Expedia
$188+ Chicago, Illinois $188: The James Chicago
Hotels.com
$118 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $118+/Nt
Expedia
$125+ Chicago, Illinois $125: Embassy Suites Chicago Downtown
Priceline.com
$79 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $79+/Nt
Expedia
$176+ Chicago, Illinois $176: Radisson Blu Aqua Hotel Chicago
Priceline.com
$84 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $84+/Nt
Expedia
$139+ Chicago, Illinois $139: ACME Hotel Company Chicago
Priceline.com
$116 Chicago, Illinois Chicago Marriott at Medical District/UIC in Dec: $116 & Up
Expedia
$169+ Chicago, Illinois $169: The Westin Chicago River North
Priceline.com
$136 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $136+/Nt
Save with Expedia, $23/night less
$79+ Chicago, Illinois $79: Best Western Grant Park, Chicago
Priceline.com
$104 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $104+/Nt
Save with Expedia, $69/night less
$103+ Chicago, Illinois $103: Millennium Knickerbocker, Chicago
Hotels.com
$99 Chicago, Illinois Book the The Palmer House Hilton 3 Nts in Dec Fr $99+/Nt
Expedia
$267+ Chicago, Illinois $267: The Peninsula Chicago
Priceline.com
$99 Chicago, Illinois Save Big This Dec! Book 3 Nts in Chicago Fr $99+/Nt
Expedia
$398+ Chicago, Illinois $398+: JW Marriott Chicago Couples' Getaway
JW Marriott Chicago
$99 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $99+/Nt
Expedia
$106 Chicago, Illinois Ray's Bucktown Bed and Breakfast
Groupon Inc
$120 Chicago, Illinois Book 4-Star Allegro Chicago - a Kimpton in Chicago Fr $120+/Nt
Save with Expedia, $13/night less
$81 Chicago, Illinois Chicago Savings! Book at River Fr $81+/Nt
Save with Expedia, $8/night less
$80 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $80+/Nt
Expedia
$120 Chicago, Illinois Dec deal: Burnham - a Kimpton Fr $120+/Nt
Save with Expedia, $13/night less
$244 Chicago, Illinois Dec deal: Park Hyatt Chicago Fr $244+/Nt
Expedia
$94 Chicago, Illinois Save in Chicago: Book 3 Nts in Dec Fr $94+/Nt
Expedia
$112 Chicago, Illinois Save in Chicago: Book 3 Nts in Dec Fr $112+/Nt
Save with Expedia, $27/night less
$120 Chicago, Illinois Swissotel Chicago in Dec: $120 & Up
Save with Expedia, $30/night less
$189 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $189+/Nt
Expedia
$89 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $89+/Nt
Expedia
$88 Chicago, Illinois Millennium Knickerbocker Chicago in Dec: $88 & Up
Expedia
PRICEDESTINATIONDEAL
$117 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$197 New York City, New York Cheap Flights from Charlotte
DealBase.com
$263 New York City, New York Cheap Flights from Salt Lake City
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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