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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$179 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$330 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $330+/Nt
Save with Expedia, $82/night less
$200 Chicago, Illinois Virgin America Great Deals Across the US
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$214 Chicago, Illinois Apr deal: Courtyard Chicago Downtown/Magnificent Mile Fr $214+/Nt
Expedia
$230 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
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$190 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $190+/Nt
Expedia
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$218 Chicago, Illinois $218 & Up: Sofitel Chicago Water Tower 4.5-Star Hotel in Chicago
Expedia
$299 Chicago, Illinois Alaska Airlines Flight Deals
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$129 Chicago, Illinois Book 3-Star Chicago South Loop Fr $129+/Nt
Expedia
$218 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
DealBase.com
$109 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $109+/Nt
Expedia
$179 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$160 Chicago, Illinois Save at 4-Star MileNorth, A Chicago: $160 & Up in Apr
Save with Expedia, $13/night less
$200 Chicago, Illinois Virgin America Great Deals Across the US
DealBase.com
$163 Chicago, Illinois Save Big This Apr! Book 3 Nts at Felix Fr $163+/Nt
Save with Expedia, $28/night less
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$199 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at The Drake Fr $199+/Nt
Expedia
$15+ Chicago, Illinois Chicago Vacation Rental Deals From $15
Tripping
$208 Chicago, Illinois Book 4.5-Star The James Chicago in Chicago Fr $208+/Nt
Expedia
$176 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $176+/Nt
Expedia
$219 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $219+/Nt
Expedia
$160 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $160+/Nt
Expedia
$169 Chicago, Illinois Small budget: Book River 3 Nts in Apr Fr $169+/Nt
Expedia
$173 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $173+/Nt
Expedia
$173 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport in Chicago Fr $173+/Nt
Expedia
$152 Chicago, Illinois Apr deal: Indigo Chicago Downtown Gold Coast Fr $152+/Nt
Expedia
$213 Chicago, Illinois Book the Embassy Suites Chicago Downtown 3 Nts in Apr Fr $213+/Nt
Expedia
$136 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $136+/Nt
Expedia
$395 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $395+/Nt
Expedia
$199 Chicago, Illinois Sheraton Chicago and Towers in Apr: $199 & Up
Expedia
$149 Chicago, Illinois Apr deal: Congress Plaza Fr $149+/Nt
Expedia
$132 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $132+/Nt
Expedia
$294 Chicago, Illinois Chicago Savings! Book at Park Hyatt Chicago Fr $294+/Nt
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$142 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $142+/Nt
Expedia
$207 Chicago, Illinois Chicago Savings! Book at Burnham - a Kimpton Fr $207+/Nt
Save with Expedia, $22/night less
$181 Chicago, Illinois Save at 4-Star Hilton Chicago: $181 & Up in Apr
Expedia
$251 Chicago, Illinois Apr deal: Chicago Marriott at Medical District/UIC Fr $251+/Nt
Expedia
$206 Chicago, Illinois Small budget: Book dana and spa 3 Nts in Apr Fr $206+/Nt
Expedia
$180 Chicago, Illinois Book in Chicago: Save this Apr Fr $180+/Nt
Expedia
$207 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $207+/Nt
Save with Expedia, $22/night less
$203 Chicago, Illinois W Chicago Lakeshore in Apr: $203 & Up
Expedia
$150 Chicago, Illinois Chicago's Essex Inn in Apr: $150 & Up
Save with Expedia, $26/night less
$301 Chicago, Illinois W Chicago - City Center on Sale: Book 3 Nts in Apr Fr $301+/Nt
Expedia
$173 Chicago, Illinois Book 3.5-Star Courtyard Chicago Downtown River North Fr $173+/Nt
Expedia
$183 Chicago, Illinois Fairmont Chicago Millennium Park in Apr: $183 & Up
Save with Expedia, $61/night less
$178 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $178+/Nt
Save with Expedia, $31/night less
$189 Chicago, Illinois Book in Chicago: Save this Apr Fr $189+/Nt
Expedia
$202 Chicago, Illinois InterContinental Chicago in Apr: $202 & Up
Expedia
$154 Chicago, Illinois Book in Chicago: Save this Apr Fr $154+/Nt
Expedia
$144 Chicago, Illinois Apr deal: Holiday Inn Chicago Downtown Fr $144+/Nt
Expedia
$106 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Apr: $106 & Up
Save with Expedia, $18/night less
$92 Chicago, Illinois Hostelling International Chicago in Apr: $92 & Up
Expedia
$183 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at The Silversmith Fr $183+/Nt
Expedia
$156 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $156+/Nt
Expedia
$209 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $209+/Nt
Expedia
$256 Chicago, Illinois Book 3.5-Star Buckingham Athletic Club Fr $256+/Nt
Expedia
$159 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $159+/Nt
Expedia
$162 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $162+/Nt
Save with Expedia, $17/night less
$159 Chicago, Illinois Book 4-Star The Whitehall Fr $159+/Nt
Expedia
$176 Chicago, Illinois Club Quarters Chicago - Central Loop in Apr: $176 & Up
Expedia
$249 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $249+/Nt
Save with Expedia, $27/night less
$138 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $138+/Nt
Expedia
$290 Chicago, Illinois Apr deal: The Ritz-Carlton Chicago (A Four Seasons ) Fr $290+/Nt
Save with Expedia, $145/night less
$154 Chicago, Illinois Warwick Allerton Chicago in Apr: $154 & Up
Expedia
$213 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $213+/Nt
Expedia
$209 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr at Central Loop Fr $209+/Nt
Expedia
$213 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $213+/Nt
Expedia
$170 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $170+/Nt
Save with Expedia, $29/night less
$246 Chicago, Illinois Special deal: 4-Star JW Marriott Chicago Fr $246+/Nt
Expedia
$165 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $165+/Nt
Expedia
$181 Chicago, Illinois Special deal: 4-Star Hard Rock Chicago Fr $181+/Nt
Save with Expedia, $32/night less
$209 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $209+/Nt
Expedia
$219 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $219+/Nt
Expedia
$153 Chicago, Illinois Chicago Savings! Book at ACME Company Chicago Fr $153+/Nt
Save with Expedia, $26/night less
$153 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $153+/Nt
Expedia
$157 Chicago, Illinois Save at 4-Star Millennium Knickerbocker Chicago: $157 & Up in Apr
Expedia
$229 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $229+/Nt
Expedia
$213 Chicago, Illinois Chicago Savings! Book at Kinzie Fr $213+/Nt
Expedia
$209 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $209+/Nt
Expedia
$203 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $203+/Nt
Expedia
$198 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $198+/Nt
Save with Expedia, $35/night less
$179 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at PUBLIC Chicago Fr $179+/Nt
Save with Expedia, $96/night less
$177 Chicago, Illinois Book in Chicago: Save this Apr Fr $177+/Nt
Save with Expedia, $20/night less
$169 Chicago, Illinois Special deal: 3-Star Comfort Suites Michigan Avenue Fr $169+/Nt
Expedia
$184 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $184+/Nt
Expedia
$395 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $395+/Nt
Expedia
$145 Chicago, Illinois Book in Chicago: Save this Apr Fr $145+/Nt
Expedia
$223 Chicago, Illinois Apr deal: Hampton Inn & Suites Chicago - Downtown Fr $223+/Nt
Expedia
$304 Chicago, Illinois Chicago Savings! Book at Four Seasons Chicago Fr $304+/Nt
Save with Expedia, $151/night less
$1,190 Chicago, Illinois Chicago 4.5-Star Hotel Sale! 3 Nts + Air Fr $1,190
Expedia
$1,310 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,310
Expedia
$576 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $576
Expedia
$819 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $819
Expedia
$2,908 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $2,908
Expedia
$913 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $913
Expedia
$1,256 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,256
Expedia
$35+ Oak Park, Illinois Oak Park Vacation Rental Deals From $35
Tripping
$113 Downers Grove, Illinois Downers Grove Savings! Book 3 Nts in Apr Fr $113+/Nt
Expedia
$50+ Evanston, Illinois Evanston Vacation Rental Deals From $50
Tripping
PRICEDESTINATIONDEAL
$117 Philadelphia, Pennsylvania Cheap Flights from Chicago
DealBase.com
$97 Philadelphia, Pennsylvania Cheap Flights from Dallas
DealBase.com
$187 Philadelphia, Pennsylvania Cheap Flights from Las Vegas
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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