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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$100+ Chicago, Illinois $100: Chicago Lake Shore Hotel
Priceline.com
$143 Chicago, Illinois $143 & Up: Felix 4-Star Hotel in Chicago
Save with Expedia, $25/night less
$101+ Chicago, Illinois $101: Millennium Knickerbocker, Chicago
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$149 Chicago, Illinois $149 & Up: Holiday Inn Chicago Downtown 3-Star Hotel in Chicago
Expedia
$103+ Chicago, Illinois $103: Chicago South Loop Hotel
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$172 Chicago, Illinois $172 & Up: The Silversmith 4-Star Hotel in Chicago
Save with Expedia, $57/night less
$105+ Chicago, Illinois $105: The Palmer House Hilton, Chicago
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$189 Chicago, Illinois $189 & Up: Hyatt Chicago Magnificent Mile 4-Star Hotel in Chicago
Expedia
$109+ Chicago, Illinois $109: The Willows Hotel, Chicago
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$1,024 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,024
Expedia
$111+ Chicago, Illinois $111: Chicago's Essex Inn
Priceline.com
$387 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $387
Expedia
$119+ Chicago, Illinois $119: Hyatt Regency Chicago
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$440 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $440
Expedia
$123+ Chicago, Illinois $123: Radisson Blu Aqua Hotel Chicago
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$261 Chicago, Illinois Alaska Airlines Flight Specials
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$129+ Chicago, Illinois $129: Raffaello Hotel, Chicago
Hotels.com
$202 Chicago, Illinois Alaska Airlines Flight Specials
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$134+ Chicago, Illinois $134: Congress Plaza Hotel, Chicago
Priceline.com
$169 Chicago, Illinois Alaska Airlines Flight Specials
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$135+ Chicago, Illinois $135: The Westin Chicago River North
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$268 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 9/11/15
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$138+ Chicago, Illinois $138: dana hotel and spa, Chicago
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$310 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 9/11/15
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$139+ Chicago, Illinois $139: The Drake Hotel, Chicago
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$280 Chicago, Illinois American Airlines Domestic Getaways for Next Weekend - 9/11/15
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$141+ Chicago, Illinois $141: Hard Rock Hotel Chicago
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$231 Chicago, Illinois American Airlines Fall & Winter Travel Deals
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$145+ Chicago, Illinois $145: PUBLIC Chicago
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$195 Chicago, Illinois American Airlines Fall & Winter Travel Deals
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$147+ Chicago, Illinois $147: Hotel Palomar Chicago, a Kimpton Hotel
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$393 Chicago, Illinois American Airlines Fall & Winter Travel Deals
DealBase.com
$149+ Chicago, Illinois $149: Crowne Plaza Chicago Metro
Hotels.com
$341 Chicago, Illinois American Airlines Fall & Winter Travel Deals
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$152+ Chicago, Illinois $152: Omni Chicago Hotel
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$245 Chicago, Illinois American Airlines Fall & Winter Travel Deals
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$153+ Chicago, Illinois $153: Kinzie Hotel, Chicago
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$305 Chicago, Illinois American Airlines Fall & Winter Travel Deals
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$178+ Chicago, Illinois $178: The James Chicago
Hotels.com
$219 Chicago, Illinois American Airlines Fall & Winter Travel Deals
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$181+ Chicago, Illinois $181: Hotel Burnham, a Kimpton Hotel, Chicago
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$379 Chicago, Illinois American Airlines Fall & Winter Travel Deals
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$188+ Chicago, Illinois $188: Loews Chicago Hotel
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$281 Chicago, Illinois American Airlines Fall & Winter Travel Deals
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$242+ Chicago, Illinois $242: Four Seasons Hotel Chicago
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$273 Chicago, Illinois American Airlines Fall & Winter Travel Deals
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$243+ Chicago, Illinois $243: The Ritz-Carlton Chicago
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$267 Chicago, Illinois American Airlines Fall & Winter Travel Deals
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$395+ Chicago, Illinois $395: The Langham Chicago
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$166 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $166+/Nt
Expedia
$71+ Chicago, Illinois $71: Inn of Chicago, an Ascend Hotel Collection Member
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$177 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $177+/Nt
Save with Expedia, $19/night less
$88+ Chicago, Illinois $88: Embassy Suites Chicago Downtown
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$199 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $199+/Nt
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$89+ Chicago, Illinois $89: City Suites Hotel, Chicago
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$206 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $206+/Nt
Expedia
$92+ Chicago, Illinois $92: ACME Hotel Company Chicago
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$229 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $229+/Nt
Save with Expedia, $57/night less
$99+ Chicago, Illinois $99: Hilton Chicago O'Hare Airport
Priceline.com
$282 Chicago, Illinois Book 3 Nts in Chicago this Sep Fr $282+/Nt
Expedia
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$219 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $219+/Nt
Expedia
$15+ Chicago, Illinois Chicago Vacation Rental Deals From $15
Tripping
$206 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $206+/Nt
Expedia
$69 Chicago, Illinois Frontier Airlines $69 Fare Sale
DealBase.com
$189 Chicago, Illinois Book 4-Star Allegro Chicago - a Kimpton Fr $189+/Nt
Expedia
$69 Chicago, Illinois Frontier Airlines $69 Fare Sale
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$199 Chicago, Illinois Book 4-Star The Drake in Chicago Fr $199+/Nt
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$39 Chicago, Illinois Frontier Airlines Last Minute Fares
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$195 Chicago, Illinois Book 4-Star The Palmer House Hilton in Chicago Fr $195+/Nt
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$49 Chicago, Illinois Frontier Airlines Last Minute Fares
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$127 Chicago, Illinois Book 4-Star The Tremont Chicago at Magnificent Mile Fr $127+/Nt
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$39 Chicago, Illinois Frontier Airlines Last Minute Fares
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$192 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $192+/Nt
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$39 Chicago, Illinois Frontier Airlines Last Minute Fares
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$138 Chicago, Illinois Book 4-Star The Whitehall Fr $138+/Nt
Save with Expedia, $25/night less
$59 Chicago, Illinois Frontier Airlines Last Minute Fares
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$440 Chicago, Illinois Book 5-Star Waldorf Astoria Chicago Fr $440+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
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$266 Chicago, Illinois Book in Chicago: Save at the Radisson Blu Aqua in Sep Fr $266+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
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$169 Chicago, Illinois Book in Chicago: Save this Sep Fr $169+/Nt
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$49 Chicago, Illinois Frontier Airlines Last Minute Fares
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$179 Chicago, Illinois Book in Chicago: Save this Sep Fr $179+/Nt
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$49 Chicago, Illinois Frontier Airlines Last Minute Fares
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$199 Chicago, Illinois Book in Chicago: Save this Sep Fr $199+/Nt
Expedia
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
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$143 Chicago, Illinois Book the BEST WESTERN Grant Park 3 Nts in Sep Fr $143+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines Last Minute Fares
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$141 Chicago, Illinois Book the Central Loop 3 Nts in Sep Fr $141+/Nt
Expedia
$39 Chicago, Illinois Frontier Airlines Last Minute Fares
DealBase.com
$1,137 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,137
Expedia
$191 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$948 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $948
Expedia
$170 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$1,912 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $1,912
Expedia
$154 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
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$193 Chicago, Illinois Chicago Marriott Downtown Magnificent Mile in Sep: $193 & Up
Expedia
$187 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
PRICEDESTINATIONDEAL
$78 Philadelphia, Pennsylvania Cheap Flights from Tampa
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$117 Philadelphia, Pennsylvania Cheap Flights from Boston
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$49 Philadelphia, Pennsylvania Frontier Airlines Last Minute Fares
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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