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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$89 Chicago, Illinois Southwest Airlines Flights on Sale
DealBase.com
$228 Chicago, Illinois United Airlines Weekend Specials for 4/24/15
DealBase.com
$224 Chicago, Illinois $224 & Up: Hilton Chicago 4-Star Hotel in Chicago
Expedia
$299 Chicago, Illinois Alaska Airlines Flight Deals
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$250 Chicago, Illinois $250 & Up: Four Seasons Chicago 5-Star Hotel in Chicago
Save with Expedia, $125/night less
$217 Chicago, Illinois American Airlines Fall Travel Deals
DealBase.com
$362 Chicago, Illinois $362 & Up: Waldorf Astoria Chicago 5-Star Hotel in Chicago
Expedia
$229 Chicago, Illinois American Airlines Spring 2015 Sale
DealBase.com
$2,005 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $2,005
Expedia
$177 Chicago, Illinois American Airlines Spring 2015 Sale
DealBase.com
$912 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $912
Expedia
$275 Chicago, Illinois American Airlines Spring 2015 Sale
DealBase.com
$187 Chicago, Illinois Apr deal: Chicago Marriott at Medical District/UIC Fr $187+/Nt
Expedia
$379 Chicago, Illinois American Airlines Spring 2015 Sale
DealBase.com
$189 Chicago, Illinois Apr deal: Club Quarters Chicago - Central Loop Fr $189+/Nt
Expedia
$277 Chicago, Illinois American Airlines Spring 2015 Sale
DealBase.com
$155 Chicago, Illinois Apr deal: Crowne Plaza Chicago - The Metro Fr $155+/Nt
Expedia
$237 Chicago, Illinois American Airlines Spring 2015 Sale
DealBase.com
$179 Chicago, Illinois Apr deal: Hilton Suites Chicago/Magnificent Mile Fr $179+/Nt
Expedia
$273 Chicago, Illinois American Airlines Spring 2015 Sale
DealBase.com
$147 Chicago, Illinois Apr deal: Holiday Inn Chicago Downtown Fr $147+/Nt
Expedia
$309 Chicago, Illinois American Airlines Spring 2015 Sale
DealBase.com
$121 Chicago, Illinois Apr deal: Indigo Chicago Downtown Gold Coast Fr $121+/Nt
Expedia
$217 Chicago, Illinois American Airlines US Spring Flight Deals
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$213 Chicago, Illinois Apr deal: Residence Inn Chicago Downtown Fr $213+/Nt
Expedia
$282 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$175 Chicago, Illinois Apr deal: theWit - A DoubleTree by Hilton Fr $175+/Nt
Expedia
$267 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$183 Chicago, Illinois BEST WESTERN Grant Park on Sale: Book 3 Nts in Apr Fr $183+/Nt
Save with Expedia, $21/night less
$269 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$129 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $129+/Nt
Expedia
$345 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$169 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $169+/Nt
Expedia
$241 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$203 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $203+/Nt
Expedia
$215 Chicago, Illinois American Airlines US Spring Flight Deals
DealBase.com
$250 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $250+/Nt
Expedia
$225 Chicago, Illinois American Airlines US Spring Flight Deals
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$197 Chicago, Illinois Book 3-Star BEST WESTERN River North in Chicago Fr $197+/Nt
Expedia
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$173 Chicago, Illinois Book 3-Star La Quinta Inn & Suites Chicago Downtown Fr $173+/Nt
Expedia
$15+ Chicago, Illinois Chicago Vacation Rental Deals From $15
Tripping
$192 Chicago, Illinois Book 4-Star Raffaello in Chicago Fr $192+/Nt
Save with Expedia, $34/night less
$122 Chicago, Illinois Southwest Airlines Flights on Sale
DealBase.com
$129 Chicago, Illinois Book 4-Star The Palmer House Hilton in Chicago Fr $129+/Nt
Expedia
$128 Chicago, Illinois Southwest Airlines Flights on Sale
DealBase.com
$156 Chicago, Illinois Book 4-Star The Tremont Chicago at Magnificent Mile Fr $156+/Nt
Expedia
$185 Chicago, Illinois Southwest Airlines Flights on Sale
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$158 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $158+/Nt
Expedia
$185 Chicago, Illinois Southwest Airlines Flights on Sale
DealBase.com
$147 Chicago, Illinois Book in Chicago: Save this Apr Fr $147+/Nt
Expedia
$115 Chicago, Illinois Southwest Airlines Flights on Sale
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$161 Chicago, Illinois Book in Chicago: Save this Apr Fr $161+/Nt
Expedia
$115 Chicago, Illinois Southwest Airlines Flights on Sale
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$173 Chicago, Illinois Book in Chicago: Save this Apr Fr $173+/Nt
Expedia
$89 Chicago, Illinois Southwest Airlines Flights on Sale
DealBase.com
$199 Chicago, Illinois Book in Chicago: Save this Apr Fr $199+/Nt
Expedia
$150 Chicago, Illinois Southwest Airlines Flights on Sale
DealBase.com
$232 Chicago, Illinois Book in Chicago: Save this Apr Fr $232+/Nt
Save with Expedia, $41/night less
$193 Chicago, Illinois Southwest Airlines Flights on Sale
DealBase.com
$256 Chicago, Illinois Book in Chicago: Save this Apr Fr $256+/Nt
Expedia
$166 Chicago, Illinois Southwest Airlines Flights on Sale
DealBase.com
$162 Chicago, Illinois Book the Omni Chicago 3 Nts in Apr Fr $162+/Nt
Save with Expedia, $17/night less
$172 Chicago, Illinois Southwest Airlines Flights on Sale
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$208 Chicago, Illinois Book the The James Chicago 3 Nts in Apr Fr $208+/Nt
Expedia
$230 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$3,776 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $3,776
Expedia
$218 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$574 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $574
Expedia
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$1,124 Chicago, Illinois Chicago 4.5-Star Hotel Sale! 3 Nts + Air Fr $1,124
Expedia
$43 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$1,236 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $1,236
Expedia
$68 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
DealBase.com
$637 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $637
Expedia
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
DealBase.com
$213 Chicago, Illinois Chicago Marriott Downtown Magnificent Mile in Apr: $213 & Up
Expedia
$38 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$149 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at Congress Plaza Fr $149+/Nt
Expedia
$23 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
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$129 Chicago, Illinois Chicago Savings! Book at Chicago South Loop Fr $129+/Nt
Expedia
$38 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
DealBase.com
$153 Chicago, Illinois Chicago Savings! Book at Chicago's Essex Inn Fr $153+/Nt
Save with Expedia, $26/night less
$93 Chicago, Illinois Spirit Airlines $9 Fare Club Deals
DealBase.com
$125 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $125+/Nt
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 4/24/15
DealBase.com
$173 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $173+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
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$207 Chicago, Illinois Chicago Savings! Book at Monaco Chicago - a Kimpton Fr $207+/Nt
Save with Expedia, $22/night less
$200 Chicago, Illinois Virgin America Great Deals Across the US
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$199 Chicago, Illinois Chicago Savings! Book at Sheraton Chicago and Towers Fr $199+/Nt
Expedia
$179 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$179 Chicago, Illinois Chicago Savings! Book at The Drake Fr $179+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
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$253 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $253+/Nt
Expedia
$179 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$189 Chicago, Illinois Hampton Inn & Suites Chicago - Downtown in Apr: $189 & Up
Expedia
$176 Chicago, Illinois Hampton Majestic Chicago Theatre District in Apr: $176 & Up
Expedia
$177 Chicago, Illinois Holiday Inn Chicago Mart Plaza River North in Apr: $177 & Up
Expedia
$92 Chicago, Illinois Hostelling International Chicago in Apr: $92 & Up
Expedia
PRICEDESTINATIONDEAL
$304 Philadelphia, Pennsylvania Cheap Flights from Denver
DealBase.com
$43 Philadelphia, Pennsylvania Spirit Airlines $9 Fare Club Deals
DealBase.com
$228 Philadelphia, Pennsylvania United Airlines Weekend Specials for 4/24/15
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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