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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$180 Chicago, Illinois $180 & Up: The Silversmith 4-Star Hotel in Chicago
Save with Expedia, $19/night less
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
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$195 Chicago, Illinois $195 & Up: The Palmer House Hilton 4-Star Hotel in Chicago
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$218 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
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$1,226 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,226
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$229 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
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$1,657 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,657
Expedia
$251 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
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$2,015 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $2,015
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$200 Chicago, Illinois Virgin America Low Fares
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$2,533 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $2,533
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$200 Chicago, Illinois Virgin America Low Fares
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$2,540 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $2,540
Expedia
$180 Chicago, Illinois Virgin America Low Fares
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$3,048 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $3,048
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$200 Chicago, Illinois Virgin America Low Fares
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$706 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $706
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$200 Chicago, Illinois Virgin America Low Fares
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$180 Chicago, Illinois BEST WESTERN Grant Park on Sale: Book 3 Nts in May Fr $180+/Nt
Save with Expedia, $20/night less
$184 Chicago, Illinois Virgin America Low Fares
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$119 Chicago, Illinois Book 3 Nts in Chicago this May Fr $119+/Nt
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$162 Chicago, Illinois Book 3 Nts in Chicago this May Fr $162+/Nt
Save with Expedia, $17/night less
$184 Chicago, Illinois Book 3 Nts in Chicago this May Fr $184+/Nt
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$199 Chicago, Illinois Book 3 Nts in Chicago this May Fr $199+/Nt
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$257 Chicago, Illinois Book 3 Nts in Chicago this May Fr $257+/Nt
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$159 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $159+/Nt
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$153 Chicago, Illinois Book 3-Star Holiday Inn Chicago Downtown in Chicago Fr $153+/Nt
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$156 Chicago, Illinois Book 3-Star Holiday Inn Express Cass Fr $156+/Nt
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$146 Chicago, Illinois Book 3-Star La Quinta Inn & Suites Chicago Downtown Fr $146+/Nt
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$134 Chicago, Illinois Book 3.5-Star River in Chicago Fr $134+/Nt
Save with Expedia, $19/night less
$198 Chicago, Illinois Book 4-Star Chicago Downtown, Autograph Collection Fr $198+/Nt
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$173 Chicago, Illinois Book 4-Star Hilton Chicago Fr $173+/Nt
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$203 Chicago, Illinois Book 4-Star MileNorth, A Chicago Fr $203+/Nt
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$133 Chicago, Illinois Book 4-Star The Tremont Chicago at Magnificent Mile Fr $133+/Nt
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$205 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $205+/Nt
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$189 Chicago, Illinois Book 4-Star theWit - A DoubleTree by Hilton Fr $189+/Nt
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$366 Chicago, Illinois Book 5-Star Waldorf Astoria Chicago in Chicago Fr $366+/Nt
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$169 Chicago, Illinois Book in Chicago: Save at the Felix in May Fr $169+/Nt
Save with Expedia, $30/night less
$178 Chicago, Illinois Book in Chicago: Save at the Hard Rock Chicago in May Fr $178+/Nt
Save with Expedia, $31/night less
$255 Chicago, Illinois Book in Chicago: Save at the Swissotel Chicago in May Fr $255+/Nt
Save with Expedia, $28/night less
$138 Chicago, Illinois Book in Chicago: Save this May Fr $138+/Nt
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$190 Chicago, Illinois Book in Chicago: Save this May Fr $190+/Nt
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$218 Chicago, Illinois Book in Chicago: Save this May Fr $218+/Nt
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$193 Chicago, Illinois Book the Burnham - a Kimpton 3 Nts in May Fr $193+/Nt
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$159 Chicago, Illinois Book the Congress Plaza 3 Nts in May Fr $159+/Nt
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$213 Chicago, Illinois Buckingham Athletic Club in May: $213 & Up
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$1,197 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $1,197
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$1,607 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,607
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$566 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $566
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$669 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $669
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$691 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $691
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$129 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $129+/Nt
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$170 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $170+/Nt
Save with Expedia, $29/night less
$194 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $194+/Nt
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$222 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $222+/Nt
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$159 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $159+/Nt
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$162 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $162+/Nt
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$226 Chicago, Illinois Chicago Savings! Book at Conrad Chicago Fr $226+/Nt
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$405 Chicago, Illinois Chicago Savings! Book at Four Seasons Chicago Fr $405+/Nt
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$169 Chicago, Illinois Chicago Savings! Book at Hyatt Regency Chicago Fr $169+/Nt
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$196 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $196+/Nt
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$415 Chicago, Illinois Chicago Savings! Book at The Peninsula Chicago Fr $415+/Nt
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$152 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $152+/Nt
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$175 Chicago, Illinois Crowne Plaza Chicago - The Metro in May: $175 & Up
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$204 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in May: $204 & Up
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$149 Chicago, Illinois Hampton Inn Chicago Downtown/Magnificent Mile in May: $149 & Up
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$190 Chicago, Illinois Hyatt Chicago Magnificent Mile in May: $190 & Up
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$112 Chicago, Illinois May deal: Central Loop Fr $112+/Nt
Save with Expedia, $27/night less
$169 Chicago, Illinois May deal: Comfort Suites Michigan Avenue Fr $169+/Nt
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$146 Chicago, Illinois May deal: Courtyard Chicago Downtown River North Fr $146+/Nt
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$198 Chicago, Illinois May deal: Fairmont Chicago Millennium Park Fr $198+/Nt
Save with Expedia, $35/night less
$209 Chicago, Illinois May deal: Hampton Majestic Chicago Theatre District Fr $209+/Nt
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$143 Chicago, Illinois May deal: Holiday Inn Chicago Mart Plaza River North Fr $143+/Nt
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$129 Chicago, Illinois May deal: Indigo Chicago Downtown Gold Coast Fr $129+/Nt
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$189 Chicago, Illinois May deal: PUBLIC Chicago Fr $189+/Nt
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$290 Chicago, Illinois May deal: The Ritz-Carlton Chicago (A Four Seasons ) Fr $290+/Nt
Save with Expedia, $145/night less
$192 Chicago, Illinois Omni Chicago in May: $192 & Up
Save with Expedia, $47/night less
$109 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in May: $109 & Up
Save with Expedia, $19/night less
$195 Chicago, Illinois Save at 3-Star Residence Inn Chicago Downtown: $195 & Up in May
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$219 Chicago, Illinois Save at 3-Star Rush: $219 & Up in May
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$117 Chicago, Illinois Save at 3.5-Star Club Quarters, Central Loop: $117 & Up in May
Save with Expedia, $29/night less
$1,756 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,756
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$1,870 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,870
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$2,007 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $2,007
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$363 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $363
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$412 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $412
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$572 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $572
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$642 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $642
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$823 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $823
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$950 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $950
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$168 Chicago, Illinois Save at 4-Star Millennium Knickerbocker Chicago: $168 & Up in May
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$184 Chicago, Illinois Save at 4-Star The Whitehall: $184 & Up in May
Save with Expedia, $25/night less
$166 Chicago, Illinois Save Big This May! Book 3 Nts at Kinzie Fr $166+/Nt
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$150 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $150+/Nt
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$166 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $166+/Nt
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$209 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $209+/Nt
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$84 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $84+/Nt
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$220 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $220+/Nt
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$224 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $224+/Nt
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$237 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $237+/Nt
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PRICEDESTINATIONDEAL
$138 Philadelphia, Pennsylvania Cheap Flights from Chicago
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$187 Philadelphia, Pennsylvania Cheap Flights from Las Vegas
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$97 Philadelphia, Pennsylvania Cheap Flights from Atlanta
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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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