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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$72 Chicago, Illinois Mar deal: Indigo Chicago Downtown Gold Coast Fr $72+/Nt
Expedia
$38+ Chicago, Illinois Dolands Addition Vacation Rental Deals From $38
Tripping
$136 Chicago, Illinois Save in Chicago: Book 3 Nts in Mar Fr $136+/Nt
Save with Expedia, $23/night less
$149 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$144 Chicago, Illinois Book 3.5-Star Hyatt Regency McCormick Place Fr $144+/Nt
Save with Expedia, $25/night less
$69 Chicago, Illinois Frontier Airlines Chicago Sale
DealBase.com
$83 Chicago, Illinois Special deal: 4-Star Raffaello Fr $83+/Nt
Save with Expedia, $45/night less
$218 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$139 Chicago, Illinois Crowne Plaza Chicago Magnificent Mile in Mar: $139 & Up
Expedia
$149 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$88 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $88+/Nt
Expedia
$69 Chicago, Illinois Frontier Airlines Chicago Sale
DealBase.com
$112 Chicago, Illinois Save in Chicago: Book 3 Nts in Mar Fr $112+/Nt
Expedia
$251 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$112 Chicago, Illinois Save in Chicago: Book 3 Nts in Mar at PUBLIC Chicago Fr $112+/Nt
Save with Expedia, $60/night less
$215 Chicago, Illinois American Airlines Spring Sale
DealBase.com
$99 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $99+/Nt
Expedia
$233 Chicago, Illinois American Airlines Spring Sale
DealBase.com
$164 Chicago, Illinois Book in Chicago: Save this Mar Fr $164+/Nt
Expedia
$205 Chicago, Illinois American Airlines Spring Sale
DealBase.com
$87 Chicago, Illinois Book the Hostelling International Chicago 3 Nts in Mar Fr $87+/Nt
Expedia
$49 Chicago, Illinois Frontier Airlines $49 Low Fare Sale
DealBase.com
$123 Chicago, Illinois Book 3.5-Star Embassy Suites Chicago Downtown Fr $123+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$139 Chicago, Illinois Book in Chicago: Save this Mar Fr $139+/Nt
Expedia
$218 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$135 Chicago, Illinois La Quinta Inn & Suites Chicago Downtown in Mar: $135 & Up
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$114 Chicago, Illinois Mar deal: Club Quarters Chicago - Central Loop Fr $114+/Nt
Save with Expedia, $12/night less
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$68 Chicago, Illinois Book 3 Nts in Chicago this Mar Fr $68+/Nt
Save with Expedia, $12/night less
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$116 Chicago, Illinois Save in Chicago: Book 3 Nts in Mar Fr $116+/Nt
Expedia
$116 Chicago, Illinois Chicago Marriott at Medical District/UIC in Mar: $116 & Up
Expedia
$126 Chicago, Illinois Book 3.5-Star River in Chicago Fr $126+/Nt
Save with Expedia, $13/night less
$174 Chicago, Illinois Mar deal: Wyndham Grand Chicago Riverfront Fr $174+/Nt
Save with Expedia, $15/night less
$127 Chicago, Illinois Book in Chicago: Save at the Hard Rock Chicago in Mar Fr $127+/Nt
Save with Expedia, $22/night less
$88 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $88+/Nt
Expedia
$112 Chicago, Illinois Book 4-Star Chicago Downtown, Autograph Collection Fr $112+/Nt
Save with Expedia, $37/night less
$164 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $164+/Nt
Expedia
$150 Chicago, Illinois Save Big This Mar! Book 3 Nts at The James Chicago Fr $150+/Nt
Save with Expedia, $26/night less
$126 Chicago, Illinois Hilton Chicago on Sale: Book 3 Nts in Mar Fr $126+/Nt
Expedia
$134 Chicago, Illinois Book 3 Nts in Chicago this Mar Fr $134+/Nt
Expedia
$167 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $167+/Nt
Expedia
$333 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $333+/Nt
Expedia
$129 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $129+/Nt
Expedia
$159 Chicago, Illinois Save at 4-Star Burnham - a Kimpton: $159 & Up in Mar
Expedia
$99 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $99+/Nt
Expedia
$153 Chicago, Illinois Book 3 Nts in Chicago this Mar Fr $153+/Nt
Expedia
$109 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $109+/Nt
Expedia
$104 Chicago, Illinois Save Big This Mar! Book 3 Nts at ACME Company Chicago Fr $104+/Nt
Save with Expedia, $19/night less
$110 Chicago, Illinois Book 3-Star Holiday Inn Chicago O'Hare in Chicago Fr $110+/Nt
Expedia
$119 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $119+/Nt
Expedia
$173 Chicago, Illinois Book the theWit - A DoubleTree by Hilton 3 Nts in Mar Fr $173+/Nt
Expedia
$117 Chicago, Illinois Small budget: Stay in Chicago this Mar Fr $117+/Nt
Expedia
$99 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $99+/Nt
Save with Expedia, $10/night less
$64 Chicago, Illinois Small budget: Stay in Chicago this Mar Fr $64+/Nt
Expedia
$259 Chicago, Illinois Save Big This Mar! Book 3 Nts in Chicago Fr $259+/Nt
Save with Expedia, $86/night less
$111 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar at Blake Chicago Fr $111+/Nt
Expedia
$100 Chicago, Illinois Save Big This Mar! Book 3 Nts in Chicago Fr $100+/Nt
Expedia
$135 Chicago, Illinois $135 & Up: dana and spa 4-Star Hotel in Chicago
Save with Expedia, $44/night less
$236 Chicago, Illinois Book the Park Hyatt Chicago 3 Nts in Mar Fr $236+/Nt
Expedia
$139 Chicago, Illinois Small budget: Book The Drake 3 Nts in Mar Fr $139+/Nt
Expedia
$85 Chicago, Illinois Book 3-Star The Tremont Chicago at Magnificent Mile Fr $85+/Nt
Expedia
$109 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $109+/Nt
Expedia
$119 Chicago, Illinois Chicago Savings! Book at Hyatt Regency Chicago Fr $119+/Nt
Expedia
$163 Chicago, Illinois Mar deal: Chicago Marriott Downtown Magnificent Mile Fr $163+/Nt
Expedia
$234 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $234+/Nt
Save with Expedia, $116/night less
$126 Chicago, Illinois Book 3.5-Star Central Loop Fr $126+/Nt
Save with Expedia, $13/night less
$177 Chicago, Illinois W Chicago - City Center on Sale: Book 3 Nts in Mar Fr $177+/Nt
Expedia
$119 Chicago, Illinois Mar deal: Comfort Suites Michigan Avenue Fr $119+/Nt
Expedia
$129 Chicago, Illinois Book 4-Star The Palmer House Hilton in Chicago Fr $129+/Nt
Expedia
$89 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $89+/Nt
Expedia
$139 Chicago, Illinois $139 & Up: Residence Inn Chicago Downtown 3-Star Hotel in Chicago
Expedia
$162 Chicago, Illinois Special deal: 4.5-Star Omni Chicago Fr $162+/Nt
Save with Expedia, $17/night less
$106 Chicago, Illinois Book in Chicago: Save this Mar Fr $106+/Nt
Expedia
$129 Chicago, Illinois Mar deal: Homewood Suites by Hilton Chicago Downtown Fr $129+/Nt
Expedia
$196 Chicago, Illinois Mar deal: Renaissance Chicago O'Hare Suites Fr $196+/Nt
Expedia
$259 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $259+/Nt
Expedia
$153 Chicago, Illinois $153 & Up: The Westin Chicago River North 4-Star Hotel in Chicago
Expedia
$219 Chicago, Illinois Book in Chicago: Save this Mar Fr $219+/Nt
Expedia
$153 Chicago, Illinois Book in Chicago: Save this Mar Fr $153+/Nt
Expedia
$148 Chicago, Illinois Book 4-Star Radisson Blu Aqua in Chicago Fr $148+/Nt
Expedia
$136 Chicago, Illinois Book in Chicago: Save this Mar Fr $136+/Nt
Save with Expedia, $34/night less
$129 Chicago, Illinois Book in Chicago: Save this Mar Fr $129+/Nt
Expedia
$138 Chicago, Illinois The Silversmith on Sale: Book 3 Nts in Mar Fr $138+/Nt
Save with Expedia, $15/night less
$100 Chicago, Illinois Save Big This Mar! Book 3 Nts in Chicago Fr $100+/Nt
Expedia
$120 Chicago, Illinois Mar deal: Fairmont Chicago Millennium Park Fr $120+/Nt
Save with Expedia, $39/night less
$114 Chicago, Illinois Chicago Savings! Book 3 Nts in Mar Fr $114+/Nt
Expedia
$90 Chicago, Illinois Congress Plaza on Sale: Book 3 Nts in Mar Fr $90+/Nt
Save with Expedia, $22/night less
$149 Chicago, Illinois Book the Hyatt Chicago Magnificent Mile 3 Nts in Mar Fr $149+/Nt
Expedia
$250 Chicago, Illinois Book the Four Seasons Chicago 3 Nts in Mar Fr $250+/Nt
Save with Expedia, $125/night less
$75 Chicago, Illinois Chicago's Essex Inn on Sale: Book 3 Nts in Mar Fr $75+/Nt
Expedia
$178 Chicago, Illinois Book 4-Star Swissotel Chicago in Chicago Fr $178+/Nt
Save with Expedia, $18/night less
$139 Chicago, Illinois Small budget: Stay in Chicago this Mar Fr $139+/Nt
Expedia
$266 Chicago, Illinois Book the The Willows 3 Nts in Mar Fr $266+/Nt
Expedia
$280 Chicago, Illinois Mar deal: Holiday Inn Express Chicago-Midway Airport Fr $280+/Nt
Expedia
$109 Chicago, Illinois Book the Hilton Chicago O'Hare Airport 3 Nts in Mar Fr $109+/Nt
Expedia
$267 Chicago, Illinois Book 3-Star Holiday Inn Chicago - Midway Airport Fr $267+/Nt
Expedia
$292 Chicago, Illinois Save Big This Mar! Book 3 Nts in Chicago Fr $292+/Nt
Save with Expedia, $73/night less
PRICEDESTINATIONDEAL
$114 Newark, New Jersey Cheap Flights from Boston
DealBase.com
$338 Newark, New Jersey Cheap Flights from Portland
DealBase.com
$229 Newark, New Jersey Cheap Flights from Milwaukee
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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