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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$142 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $142+/Nt
Expedia
$10 Chicago, Illinois Cheap Car Rentals in Chicago Fr $10/Day
CarRentals.com
$169 Chicago, Illinois Comfort Suites Michigan Avenue in Apr: $169 & Up
Expedia
$15+ Chicago, Illinois Chicago Vacation Rental Deals From $15
Tripping
$92 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $92+/Nt
Expedia
$230 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$130 Chicago, Illinois Apr deal: Indigo Chicago Downtown Gold Coast Fr $130+/Nt
Expedia
$299 Chicago, Illinois Alaska Airlines Flight Deals
DealBase.com
$239 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Apr: $239 & Up
Expedia
$179 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$190 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $190+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$129 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $129+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$218 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $218+/Nt
Expedia
$218 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$109 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $109+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$163 Chicago, Illinois Special deal: 4-Star Felix Fr $163+/Nt
Save with Expedia, $28/night less
$179 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$160 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $160+/Nt
Save with Expedia, $13/night less
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$199 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $199+/Nt
Expedia
$208 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $208+/Nt
Expedia
$219 Chicago, Illinois Apr deal: Renaissance Chicago Fr $219+/Nt
Expedia
$169 Chicago, Illinois Small budget: Book River 3 Nts in Apr Fr $169+/Nt
Expedia
$160 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $160+/Nt
Expedia
$102 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $102+/Nt
Save with Expedia, $33/night less
$330 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $330+/Nt
Save with Expedia, $82/night less
$173 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $173+/Nt
Expedia
$136 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $136+/Nt
Expedia
$213 Chicago, Illinois Embassy Suites Chicago Downtown in Apr: $213 & Up
Expedia
$395 Chicago, Illinois Book 5-Star The Peninsula Chicago Fr $395+/Nt
Expedia
$221 Chicago, Illinois Book 4-Star The Westin Chicago River North in Chicago Fr $221+/Nt
Expedia
$147 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $147+/Nt
Expedia
$149 Chicago, Illinois Book 3-Star Congress Plaza in Chicago Fr $149+/Nt
Expedia
$199 Chicago, Illinois Sheraton Chicago and Towers in Apr: $199 & Up
Expedia
$202 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $202+/Nt
Save with Expedia, $67/night less
$207 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $207+/Nt
Save with Expedia, $22/night less
$181 Chicago, Illinois Book the Hilton Chicago 3 Nts in Apr Fr $181+/Nt
Expedia
$211 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at PUBLIC Chicago Fr $211+/Nt
Save with Expedia, $64/night less
$251 Chicago, Illinois Chicago Marriott at Medical District/UIC in Apr: $251 & Up
Expedia
$219 Chicago, Illinois Book 4-Star The Whitehall in Chicago Fr $219+/Nt
Expedia
$156 Chicago, Illinois Apr deal: Club Quarters Chicago - Central Loop Fr $156+/Nt
Expedia
$206 Chicago, Illinois Book 4-Star dana and spa Fr $206+/Nt
Expedia
$207 Chicago, Illinois Save at 4-Star Palomar Chicago, a Kimpton: $207 & Up in Apr
Save with Expedia, $22/night less
$179 Chicago, Illinois Apr deal: La Quinta Inn & Suites Chicago Downtown Fr $179+/Nt
Expedia
$173 Chicago, Illinois Book 3.5-Star Courtyard Chicago Downtown River North Fr $173+/Nt
Expedia
$150 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $150+/Nt
Save with Expedia, $26/night less
$301 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $301+/Nt
Expedia
$183 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $183+/Nt
Save with Expedia, $61/night less
$183 Chicago, Illinois Book in Chicago: Save this Apr Fr $183+/Nt
Expedia
$178 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $178+/Nt
Save with Expedia, $31/night less
$189 Chicago, Illinois The Palmer House Hilton on Sale: Book 3 Nts in Apr Fr $189+/Nt
Expedia
$202 Chicago, Illinois InterContinental Chicago in Apr: $202 & Up
Expedia
$176 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $176+/Nt
Expedia
$154 Chicago, Illinois Hilton Suites Chicago/Magnificent Mile in Apr: $154 & Up
Expedia
$144 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $144+/Nt
Expedia
$166 Chicago, Illinois Special deal: 3.5-Star Central Loop Fr $166+/Nt
Expedia
$106 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $106+/Nt
Save with Expedia, $18/night less
$187 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $187+/Nt
Expedia
$150 Chicago, Illinois The Tremont Chicago at Magnificent Mile in Apr: $150 & Up
Expedia
$209 Chicago, Illinois Hampton Inn Chicago Downtown/Magnificent Mile in Apr: $209 & Up
Expedia
$159 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $159+/Nt
Expedia
$172 Chicago, Illinois Raffaello in Apr: $172 & Up
Save with Expedia, $31/night less
$162 Chicago, Illinois Small budget: Book Omni Chicago 3 Nts in Apr Fr $162+/Nt
Save with Expedia, $17/night less
$290 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $290+/Nt
Save with Expedia, $145/night less
$185 Chicago, Illinois Apr deal: Holiday Inn Chicago Mart Plaza River North Fr $185+/Nt
Expedia
$262 Chicago, Illinois Apr deal: Radisson Blu Aqua Fr $262+/Nt
Expedia
$181 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $181+/Nt
Expedia
$246 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $246+/Nt
Expedia
$346 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $346+/Nt
Expedia
$196 Chicago, Illinois Kinzie in Apr: $196 & Up
Expedia
$181 Chicago, Illinois $181 & Up: Hard Rock Chicago 4-Star Hotel in Chicago
Save with Expedia, $32/night less
$206 Chicago, Illinois Save at 3-Star Residence Inn Chicago Downtown: $206 & Up in Apr
Expedia
$219 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $219+/Nt
Expedia
$205 Chicago, Illinois Hampton Inn & Suites Chicago - Downtown in Apr: $205 & Up
Expedia
$153 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $153+/Nt
Save with Expedia, $26/night less
$207 Chicago, Illinois Book 4-Star Swissotel Chicago Fr $207+/Nt
Save with Expedia, $23/night less
$153 Chicago, Illinois Book the Blake Chicago 3 Nts in Apr Fr $153+/Nt
Expedia
$157 Chicago, Illinois Save at 4-Star Millennium Knickerbocker Chicago: $157 & Up in Apr
Expedia
$199 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $199+/Nt
Expedia
$203 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $203+/Nt
Expedia
$209 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $209+/Nt
Expedia
$177 Chicago, Illinois Book the BEST WESTERN Grant Park 3 Nts in Apr Fr $177+/Nt
Save with Expedia, $20/night less
$198 Chicago, Illinois Wyndham Grand Chicago Riverfront in Apr: $198 & Up
Save with Expedia, $35/night less
$175 Chicago, Illinois Apr deal: theWit - A DoubleTree by Hilton Fr $175+/Nt
Expedia
$184 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $184+/Nt
Expedia
$395 Chicago, Illinois Book 5-Star Waldorf Astoria Chicago in Chicago Fr $395+/Nt
Expedia
$236 Chicago, Illinois Book 3.5-Star Buckingham Athletic Club in Chicago Fr $236+/Nt
Expedia
$136 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $136+/Nt
Expedia
$304 Chicago, Illinois Chicago Savings! Book at Four Seasons Chicago Fr $304+/Nt
Save with Expedia, $151/night less
$176 Chicago, Illinois Book the Rush 3 Nts in Apr Fr $176+/Nt
Expedia
$908 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $908
Expedia
$535 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $535
Expedia
$718 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $718
Expedia
$2,005 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $2,005
Expedia
$2,113 Chicago, Illinois Save at 4.5-Star Hotel: 3 Nts + Air to Chicago Fr $2,113
Expedia
$35+ Oak Park, Illinois Oak Park Vacation Rental Deals From $35
Tripping
$153 Bedford Park, Illinois Hilton Garden Inn Chicago Midway Airport in Apr: $153 & Up
Expedia
PRICEDESTINATIONDEAL
$187 Philadelphia, Pennsylvania Cheap Flights from Las Vegas
DealBase.com
$304 Philadelphia, Pennsylvania Cheap Flights from Denver
DealBase.com
$327 Philadelphia, Pennsylvania Cheap Flights from Phoenix
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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