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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$576 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $576
Expedia
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$226 Chicago, Illinois Book 4-Star dana and spa in Chicago Fr $226+/Nt
Expedia
$15+ Chicago, Illinois Chicago Vacation Rental Deals From $15
Tripping
$153 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $153+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$1,479 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,479
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$1,082 Chicago, Illinois Chicago 4.5-Star Hotel Sale! 3 Nts + Air Fr $1,082
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$263 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $263+/Nt
Expedia
$230 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$249 Chicago, Illinois Chicago Savings! Book at Swissotel Chicago Fr $249+/Nt
Save with Expedia, $27/night less
$179 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$276 Chicago, Illinois Apr deal: Hilton Chicago O'Hare Airport Fr $276+/Nt
Expedia
$299 Chicago, Illinois Alaska Airlines Flight Deals
DealBase.com
$209 Chicago, Illinois The Whitehall in Apr: $209 & Up
Expedia
$218 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$301 Chicago, Illinois Chicago Savings! Book at W Chicago - City Center Fr $301+/Nt
Expedia
$179 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$195 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $195+/Nt
Expedia
$141 Chicago, Illinois Book 3.5-Star Blake Chicago Fr $141+/Nt
Expedia
$189 Chicago, Illinois Book the BEST WESTERN Grant Park 3 Nts in Apr Fr $189+/Nt
Save with Expedia, $21/night less
$198 Chicago, Illinois Save at 4.5-Star Omni Chicago: $198 & Up in Apr
Save with Expedia, $21/night less
$330 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $330+/Nt
Save with Expedia, $82/night less
$173 Chicago, Illinois Small budget: Book The Silversmith 3 Nts in Apr Fr $173+/Nt
Expedia
$216 Chicago, Illinois Book the InterContinental Chicago 3 Nts in Apr Fr $216+/Nt
Expedia
$213 Chicago, Illinois $213 & Up: Radisson Blu Aqua 4.5-Star Hotel in Chicago
Expedia
$290 Chicago, Illinois Apr deal: The Ritz-Carlton Chicago (A Four Seasons ) Fr $290+/Nt
Save with Expedia, $145/night less
$184 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $184+/Nt
Expedia
$187 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $187+/Nt
Expedia
$183 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $183+/Nt
Expedia
$224 Chicago, Illinois Book the The Blackstone A Renaissance 3 Nts in Apr Fr $224+/Nt
Expedia
$109 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $109+/Nt
Expedia
$199 Chicago, Illinois Chicago Downtown, Autograph Collection in Apr: $199 & Up
Expedia
$141 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $141+/Nt
Save with Expedia, $25/night less
$138 Chicago, Illinois Book 4-Star The Tremont Chicago at Magnificent Mile Fr $138+/Nt
Expedia
$180 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $180+/Nt
Save with Expedia, $19/night less
$190 Chicago, Illinois Book the Holiday Inn Chicago Downtown 3 Nts in Apr Fr $190+/Nt
Expedia
$156 Chicago, Illinois Book in Chicago: Save this Apr Fr $156+/Nt
Expedia
$304 Chicago, Illinois Four Seasons Chicago on Sale: Book 3 Nts in Apr Fr $304+/Nt
Save with Expedia, $151/night less
$87 Chicago, Illinois Apr deal: Hostelling International Chicago Fr $87+/Nt
Expedia
$229 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $229+/Nt
Expedia
$158 Chicago, Illinois Save at 4-Star Hard Rock Chicago: $158 & Up in Apr
Save with Expedia, $28/night less
$150 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $150+/Nt
Save with Expedia, $26/night less
$170 Chicago, Illinois Book in Chicago: Save at the Raffaello in Apr Fr $170+/Nt
Save with Expedia, $29/night less
$407 Chicago, Illinois $407 & Up: The Peninsula Chicago 5-Star Hotel in Chicago
Expedia
$176 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at Felix Fr $176+/Nt
Save with Expedia, $31/night less
$224 Chicago, Illinois Hilton Chicago in Apr: $224 & Up
Expedia
$236 Chicago, Illinois Book 3.5-Star Buckingham Athletic Club in Chicago Fr $236+/Nt
Expedia
$133 Chicago, Illinois $133 & Up: Chicago South Loop 3-Star Hotel in Chicago
Expedia
$225 Chicago, Illinois Special deal: 4.5-Star Sofitel Chicago Water Tower Fr $225+/Nt
Expedia
$149 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $149+/Nt
Expedia
$199 Chicago, Illinois Special deal: 4-Star Sheraton Chicago and Towers Fr $199+/Nt
Expedia
$187 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $187+/Nt
Expedia
$204 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $204+/Nt
Save with Expedia, $35/night less
$131 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Apr: $131 & Up
Save with Expedia, $22/night less
$160 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $160+/Nt
Expedia
$138 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $138+/Nt
Expedia
$180 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $180+/Nt
Expedia
$2,403 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $2,403
Expedia
$182 Chicago, Illinois Holiday Inn Chicago Mart Plaza River North in Apr: $182 & Up
Expedia
$250 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $250+/Nt
Expedia
$176 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $176+/Nt
Expedia
$176 Chicago, Illinois Book 3.5-Star Central Loop in Chicago Fr $176+/Nt
Expedia
$160 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Apr: $160 & Up
Expedia
$346 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $346+/Nt
Expedia
$269 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $269+/Nt
Expedia
$207 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $207+/Nt
Save with Expedia, $22/night less
$193 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $193+/Nt
Expedia
$206 Chicago, Illinois Apr deal: Comfort Suites Michigan Avenue Fr $206+/Nt
Expedia
$243 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $243+/Nt
Expedia
$229 Chicago, Illinois Book the The Palmer House Hilton 3 Nts in Apr Fr $229+/Nt
Expedia
$186 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $186+/Nt
Expedia
$184 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $184+/Nt
Expedia
$157 Chicago, Illinois Millennium Knickerbocker Chicago in Apr: $157 & Up
Expedia
$163 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr at Kinzie Fr $163+/Nt
Expedia
$199 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $199+/Nt
Expedia
$145 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $145+/Nt
Expedia
$129 Chicago, Illinois Save at 3-Star Holiday Inn Express Cass: $129 & Up in Apr
Expedia
$1,256 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,256
Expedia
$188 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $188+/Nt
Save with Expedia, $101/night less
$206 Chicago, Illinois Apr deal: Chicago Marriott Downtown Magnificent Mile Fr $206+/Nt
Expedia
$208 Chicago, Illinois Small budget: Book The James Chicago 3 Nts in Apr Fr $208+/Nt
Expedia
$236 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $236+/Nt
Expedia
$198 Chicago, Illinois Burnham - a Kimpton in Apr: $198 & Up
Save with Expedia, $21/night less
$199 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $199+/Nt
Expedia
$173 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $173+/Nt
Expedia
$183 Chicago, Illinois Save at 4-Star Fairmont Chicago Millennium Park: $183 & Up in Apr
Save with Expedia, $61/night less
$226 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $226+/Nt
Expedia
$35+ Oak Park, Illinois Oak Park Vacation Rental Deals From $35
Tripping
$141 Alsip, Illinois Special deal: 3.5-Star Doubletree Chicago / Alsip Fr $141+/Nt
Expedia
$43+ Downers Grove, Illinois Downers Grove Vacation Rental Deals From $43
Tripping
$119 Arlington Heights, Illinois Save in Arlington Heights: Book 3 Nts in Apr Fr $119+/Nt
Expedia
$59+ Elmhurst, Illinois Elmhurst Vacation Rental Deals From $59
Tripping
$230 Bedford Park, Illinois Book 3-Star Hilton Garden Inn Chicago Midway Airport Fr $230+/Nt
Expedia
$50+ Evanston, Illinois Evanston Vacation Rental Deals From $50
Tripping
$190 Bedford Park, Illinois Hampton Inn Chicago-Midway Airport in Apr: $190 & Up
Expedia
$81 Bensenville, Illinois Country Inn & Suites O'Hare South in Apr: $81 & Up
Expedia
$126 Bloomingdale, Illinois Hilton Chicago/Indian Lakes in Apr: $126 & Up
Expedia
PRICEDESTINATIONDEAL
$187 Philadelphia, Pennsylvania Cheap Flights from Las Vegas
DealBase.com
$304 Philadelphia, Pennsylvania Cheap Flights from Denver
DealBase.com
$447 Philadelphia, Pennsylvania Cheap Flights from San Francisco
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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