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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$281 Chicago, Illinois American Airlines Fall & Winter Travel Deals
DealBase.com
$141 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug at Central Loop Fr $141+/Nt
Expedia
$287 Chicago, Illinois American Airlines Fall & Winter Travel Deals
DealBase.com
$213 Chicago, Illinois Aug deal: InterContinental Chicago Fr $213+/Nt
Expedia
$29 Chicago, Illinois Frontier Airlines Discount Den Deals
DealBase.com
$189 Chicago, Illinois Aug deal: Hampton Inn & Suites Chicago - Downtown Fr $189+/Nt
Expedia
$187 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$150 Chicago, Illinois Aug deal: Blake Chicago Fr $150+/Nt
Expedia
$305 Chicago, Illinois American Airlines Fall & Winter Travel Deals
DealBase.com
$180 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $180+/Nt
Expedia
$139 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$176 Chicago, Illinois Aug deal: Homewood Suites by Hilton Chicago Downtown Fr $176+/Nt
Expedia
$154 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$110 Chicago, Illinois Special deal: 3-Star Chicago South Loop Fr $110+/Nt
Save with Expedia, $19/night less
$116 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$213 Chicago, Illinois Aug deal: Embassy Suites by Hilton Chicago Downtown Fr $213+/Nt
Expedia
$200 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$179 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $179+/Nt
Expedia
$69 Chicago, Illinois Frontier Airlines $69 Fare Sale
DealBase.com
$229 Chicago, Illinois Special deal: 4-Star theWit - A DoubleTree by Hilton Fr $229+/Nt
Expedia
$219 Chicago, Illinois American Airlines Fall & Winter Travel Deals
DealBase.com
$201 Chicago, Illinois Book 4-Star Wyndham Grand Chicago Riverfront Fr $201+/Nt
Save with Expedia, $35/night less
$69 Chicago, Illinois Frontier Airlines $69 Fare Sale
DealBase.com
$138+ Chicago, Illinois $138: dana hotel and spa, Chicago
Priceline.com
$116 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$186 Chicago, Illinois Special deal: 3-Star AC Chicago Downtown Fr $186+/Nt
Expedia
$171 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$149 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $149+/Nt
Expedia
$180 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$185 Chicago, Illinois Chicago Savings! Book at Hyatt Regency Chicago Fr $185+/Nt
Expedia
$217 Chicago, Illinois Alaska Airlines Flight Specials
DealBase.com
$179 Chicago, Illinois Book 3.5-Star Courtyard Chicago Downtown River North Fr $179+/Nt
Expedia
$327 Chicago, Illinois American Airlines Fall & Winter Travel Deals
DealBase.com
$100 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $100+/Nt
Expedia
$169 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$136 Chicago, Illinois Book 3 Nts in Chicago this Aug Fr $136+/Nt
Expedia
$231 Chicago, Illinois American Airlines Fall & Winter Travel Deals
DealBase.com
$304 Chicago, Illinois Chicago Savings! Book at Four Seasons Chicago Fr $304+/Nt
Save with Expedia, $151/night less
$393 Chicago, Illinois American Airlines Fall & Winter Travel Deals
DealBase.com
$150 Chicago, Illinois $150 & Up: River 3.5-Star Hotel in Chicago
Expedia
$187 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$165 Chicago, Illinois Small budget: Book dana and spa 3 Nts in Aug Fr $165+/Nt
Save with Expedia, $41/night less
$191 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$150 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $150+/Nt
Expedia
$120 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$263 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $263+/Nt
Expedia
$200 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$141 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $141+/Nt
Save with Expedia, $25/night less
$126 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$153+ Chicago, Illinois $153: Kinzie Hotel, Chicago
Priceline.com
$200 Chicago, Illinois Virgin America Land the Lowest Fares Promotion
DealBase.com
$161 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug at Raffaello Fr $161+/Nt
Save with Expedia, $28/night less
$159 Chicago, Illinois Alaska Airlines Flight Specials
DealBase.com
$166 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $166+/Nt
Expedia
$170 Chicago, Illinois Southwest Airlines Fall & Winter Travel Deals
DealBase.com
$123 Chicago, Illinois Aug deal: Holiday Inn Express Cass Fr $123+/Nt
Expedia
$379 Chicago, Illinois American Airlines Fall & Winter Travel Deals
DealBase.com
$117 Chicago, Illinois Hostelling International Chicago in Aug: $117 & Up
Expedia
$197 Chicago, Illinois American Airlines Fall & Winter Travel Deals
DealBase.com
$145+ Chicago, Illinois $145: PUBLIC Chicago
Priceline.com
$281 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $281+/Nt
Expedia
$129+ Chicago, Illinois $129: Raffaello Hotel, Chicago
Hotels.com
$180 Chicago, Illinois Book 3-Star La Quinta Inn & Suites Chicago Downtown Fr $180+/Nt
Expedia
$149+ Chicago, Illinois $149: Crowne Plaza Chicago Metro
Hotels.com
$330 Chicago, Illinois Aug deal: Trump International & Tower Chicago Fr $330+/Nt
Save with Expedia, $82/night less
$119+ Chicago, Illinois $119: The Palmer House Hilton, Chicago
Priceline.com
$155 Chicago, Illinois Book in Chicago: Save this Aug Fr $155+/Nt
Save with Expedia, $28/night less
$92+ Chicago, Illinois $92: ACME Hotel Company Chicago
Priceline.com
$169 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $169+/Nt
Expedia
$103+ Chicago, Illinois $103: Chicago South Loop Hotel
Priceline.com
$219 Chicago, Illinois Special deal: 4-Star The Blackstone A Renaissance Fr $219+/Nt
Expedia
$178+ Chicago, Illinois $178: The James Chicago
Hotels.com
$135 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $135+/Nt
Expedia
$152+ Chicago, Illinois $152: Omni Chicago Hotel
Priceline.com
$178 Chicago, Illinois Chicago Savings! Book at Hard Rock Chicago Fr $178+/Nt
Save with Expedia, $31/night less
$135+ Chicago, Illinois $135: The Westin Chicago River North
Priceline.com
$199 Chicago, Illinois Small budget: Stay in Chicago this Aug Fr $199+/Nt
Expedia
$101+ Chicago, Illinois $101: Millennium Knickerbocker, Chicago
Priceline.com
$161 Chicago, Illinois Chicago Savings! Book at BEST WESTERN Grant Park Fr $161+/Nt
Expedia
$181+ Chicago, Illinois $181: Hotel Burnham, a Kimpton Hotel, Chicago
Priceline.com
$366 Chicago, Illinois Book the Waldorf Astoria Chicago 3 Nts in Aug Fr $366+/Nt
Expedia
$147+ Chicago, Illinois $147: Hotel Palomar Chicago, a Kimpton Hotel
Priceline.com
$229 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $229+/Nt
Expedia
$15+ Chicago, Illinois Chicago Vacation Rental Deals From $15
Tripping
$249 Chicago, Illinois Chicago Savings! Book at Conrad Chicago Fr $249+/Nt
Expedia
$89+ Chicago, Illinois $89: Warwick Allerton Hotel Chicago
Priceline.com
$129 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $129+/Nt
Expedia
$134+ Chicago, Illinois $134: Congress Plaza Hotel, Chicago
Priceline.com
$189 Chicago, Illinois Book 3-Star Comfort Suites Michigan Avenue in Chicago Fr $189+/Nt
Expedia
$141+ Chicago, Illinois $141: Hard Rock Hotel Chicago
Priceline.com
$138 Chicago, Illinois Chicago Savings! Book at Congress Plaza Fr $138+/Nt
Save with Expedia, $15/night less
$395+ Chicago, Illinois $395: The Peninsula Chicago
Priceline.com
$149 Chicago, Illinois Special deal: 4-Star The Whitehall Fr $149+/Nt
Expedia
$105+ Chicago, Illinois $105: The Palmer House Hilton, Chicago
Priceline.com
$143 Chicago, Illinois Hilton Chicago O'Hare Airport in Aug: $143 & Up
Expedia
$111+ Chicago, Illinois $111: Chicago's Essex Inn
Priceline.com
$113 Chicago, Illinois Aug deal: The Tremont Chicago at Magnificent Mile Fr $113+/Nt
Expedia
$242+ Chicago, Illinois $242: Four Seasons Hotel Chicago
Priceline.com
$149 Chicago, Illinois Book 3 Nts in Chicago this Aug Fr $149+/Nt
Expedia
$123+ Chicago, Illinois $123: Radisson Blu Aqua Hotel Chicago
Priceline.com
PRICEDESTINATIONDEAL
$257 Newark, New Jersey Cheap Flights from Denver
DealBase.com
$237 Newark, New Jersey Cheap Flights from Nashville
DealBase.com
$199 Newark, New Jersey Alaska Airlines Flight Specials
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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