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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$103+ Chicago, Illinois $103: Millennium Knickerbocker, Chicago
Hotels.com
$146 Chicago, Illinois $146 & Up: PUBLIC Chicago 4-Star Hotel in Chicago
Expedia
$129+ Chicago, Illinois $129: Courtyard by Marriott Chicago Magnificent Mile
Priceline.com
$354 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $354
Expedia
$132+ Chicago, Illinois $132: SpringHill Suites Chicago O'Hare by Marriott
Priceline.com
$653 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $653
Expedia
$135+ Chicago, Illinois $135: Conrad Chicago
Priceline.com
$85+ Chicago, Illinois 4-Star Chicago Hotels from $85
trivago
$139+ Chicago, Illinois $139: ACME Hotel Company Chicago
Priceline.com
$494 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $494
Expedia
$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
Priceline.com
$930 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $930
Expedia
$157+ Chicago, Illinois $157: The Buckingham Athletic Club & Hotel, Chicago
Priceline.com
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$158+ Chicago, Illinois $158: dana hotel and spa, Chicago
Priceline.com
$225 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$169+ Chicago, Illinois $169: The Westin Chicago River North
Priceline.com
$279 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$170+ Chicago, Illinois $170: Warwick Allerton Hotel Chicago
Hotels.com
$275 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$175+ Chicago, Illinois $175: Ruby Room, Chicago
Priceline.com
$271 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$176+ Chicago, Illinois $176: Radisson Blu Aqua Hotel Chicago
Priceline.com
$291 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$179+ Chicago, Illinois $179: Embassy Suites Chicago Downtown - Lakefront
Priceline.com
$239 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$212+ Chicago, Illinois $212: Fairmont Chicago at Millennium Park
Hotels.com
$245 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$267+ Chicago, Illinois $267: The Peninsula Chicago
Priceline.com
$213 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$398+ Chicago, Illinois $398+: JW Marriott Chicago Couples' Getaway
JW Marriott Chicago
$241 Chicago, Illinois American Airlines US Flight Deals
DealBase.com
$79+ Chicago, Illinois $79: Best Western Grant Park, Chicago
Priceline.com
$119 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $119+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$264 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $264+/Nt
Save with Expedia, $131/night less
$31 Chicago, Illinois Chicago Vacation Rental Deals From $31
Tripping
$79 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $79+/Nt
Expedia
$106 Chicago, Illinois Ray's Bucktown Bed and Breakfast
Groupon Inc
$89 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $89+/Nt
Expedia
$140 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$90 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $90+/Nt
Expedia
$153 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$99 Chicago, Illinois Book 3 Nts in Chicago this Dec Fr $99+/Nt
Expedia
$164 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$96 Chicago, Illinois Book 3-Star Comfort Suites Michigan Avenue in Chicago Fr $96+/Nt
Expedia
$113 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$159 Chicago, Illinois Book 3.5-Star Renaissance Chicago in Chicago Fr $159+/Nt
Expedia
$126 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$85 Chicago, Illinois Book 4-Star Hilton Chicago in Chicago Fr $85+/Nt
Expedia
$90 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$80 Chicago, Illinois Book 4-Star Hyatt Regency Chicago in Chicago Fr $80+/Nt
Save with Expedia, $19/night less
$133 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$93 Chicago, Illinois Book 4.5-Star InterContinental Chicago in Chicago Fr $93+/Nt
Expedia
$112 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$126 Chicago, Illinois Book 4.5-Star Omni Chicago in Chicago Fr $126+/Nt
Save with Expedia, $13/night less
$114 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$112 Chicago, Illinois Book 4.5-Star Sofitel Chicago Water Tower in Chicago Fr $112+/Nt
Expedia
$117 Chicago, Illinois Southwest Airlines Resolve to Have an Adventure
DealBase.com
$165 Chicago, Illinois Book in Chicago: Save at the Conrad Chicago in Dec Fr $165+/Nt
Expedia
$135 Chicago, Illinois United Airlines US Fare Sale
DealBase.com
$112 Chicago, Illinois Book in Chicago: Save at the The James Chicago in Dec Fr $112+/Nt
Save with Expedia, $27/night less
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$100 Chicago, Illinois Book in Chicago: Save this Dec Fr $100+/Nt
Expedia
$169 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$126 Chicago, Illinois Book in Chicago: Save this Dec Fr $126+/Nt
Save with Expedia, $13/night less
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$81 Chicago, Illinois Book in Chicago: Save this Dec Fr $81+/Nt
Save with Expedia, $8/night less
$179 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$94 Chicago, Illinois Book in Chicago: Save this Dec Fr $94+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$99 Chicago, Illinois Book in Chicago: Save this Dec Fr $99+/Nt
Expedia
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$86 Chicago, Illinois Book the Hyatt Regency McCormick Place 3 Nts in Dec Fr $86+/Nt
Expedia
$244 Chicago, Illinois Book the Park Hyatt Chicago 3 Nts in Dec Fr $244+/Nt
Expedia
$109 Chicago, Illinois Book the Residence Inn Chicago Downtown 3 Nts in Dec Fr $109+/Nt
Expedia
$81 Chicago, Illinois Book the River 3 Nts in Dec Fr $81+/Nt
Save with Expedia, $8/night less
$109 Chicago, Illinois Book the Sheraton Chicago and Towers 3 Nts in Dec Fr $109+/Nt
Expedia
$112 Chicago, Illinois Book the W Chicago - City Center 3 Nts in Dec Fr $112+/Nt
Expedia
$293 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $293
Expedia
$447 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $447
Expedia
$116 Chicago, Illinois Chicago Marriott at Medical District/UIC in Dec: $116 & Up
Expedia
$129 Chicago, Illinois Chicago Marriott Downtown Magnificent Mile in Dec: $129 & Up
Expedia
$114 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $114+/Nt
Expedia
$128 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $128+/Nt
Expedia
$77 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $77+/Nt
Save with Expedia, $32/night less
$79 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $79+/Nt
Expedia
$79 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $79+/Nt
Save with Expedia, $14/night less
$92 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $92+/Nt
Expedia
$120 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $120+/Nt
Save with Expedia, $13/night less
$68 Chicago, Illinois Chicago Savings! Book at Chicago's Essex Inn Fr $68+/Nt
Save with Expedia, $11/night less
$119 Chicago, Illinois Chicago Savings! Book at dana and spa Fr $119+/Nt
Expedia
$79 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $79+/Nt
Expedia
$189 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $189+/Nt
Expedia
$104 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $104+/Nt
Save with Expedia, $69/night less
$126 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $126+/Nt
Save with Expedia, $13/night less
$59 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $59+/Nt
Expedia
$294 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $294+/Nt
Expedia
$119 Chicago, Illinois Dec deal: Buckingham Athletic Club Fr $119+/Nt
Save with Expedia, $20/night less
$91 Chicago, Illinois Dec deal: Crowne Plaza Chicago - The Metro Fr $91+/Nt
Save with Expedia, $8/night less
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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