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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$228 Chicago, Illinois United Airlines Weekend Specials for 5/29/15
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$89 Chicago, Illinois Southwest Airlines Autumn Escape Sale
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$128 Chicago, Illinois Southwest Airlines Summer Travel Deals
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$180 Chicago, Illinois Book 3 Nts in Chicago this May Fr $180+/Nt
Save with Expedia, $20/night less
$218 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
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$134 Chicago, Illinois Chicago Savings! Book 3 Nts in May at River Fr $134+/Nt
Save with Expedia, $19/night less
$207 Chicago, Illinois Southwest Airlines Summer Travel Deals
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$196 Chicago, Illinois Chicago Savings! Book at Palomar Chicago, a Kimpton Fr $196+/Nt
Expedia
$328 Chicago, Illinois United Airlines Weekend Specials for 5/29/15
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$136 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport Fr $136+/Nt
Expedia
$149 Chicago, Illinois Southwest Airlines Summer Travel Deals
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$240 Chicago, Illinois May deal: Courtyard Chicago Downtown/Magnificent Mile Fr $240+/Nt
Expedia
$139 Chicago, Illinois Southwest Airlines Summer Travel Deals
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$233 Chicago, Illinois Small budget: Stay in Chicago this May Fr $233+/Nt
Expedia
$229 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
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$219 Chicago, Illinois Homewood Suites by Hilton Chicago Downtown in May: $219 & Up
Expedia
$166 Chicago, Illinois Southwest Airlines Autumn Escape Sale
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$167 Chicago, Illinois Blake Chicago on Sale: Book 3 Nts in May Fr $167+/Nt
Expedia
$115 Chicago, Illinois Southwest Airlines Autumn Escape Sale
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$240 Chicago, Illinois Book in Chicago: Save this May Fr $240+/Nt
Save with Expedia, $59/night less
$135 Chicago, Illinois Southwest Airlines Summer Travel Deals
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$129 Chicago, Illinois Book in Chicago: Save this May Fr $129+/Nt
Expedia
$139 Chicago, Illinois Southwest Airlines Summer Travel Deals
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$237 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $237+/Nt
Expedia
$189 Chicago, Illinois Southwest Airlines Summer Travel Deals
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$209 Chicago, Illinois Book in Chicago: Save this May Fr $209+/Nt
Expedia
$155 Chicago, Illinois Southwest Airlines Autumn Escape Sale
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$117 Chicago, Illinois Chicago Savings! Book at Club Quarters, Central Loop Fr $117+/Nt
Save with Expedia, $29/night less
$242 Chicago, Illinois Southwest Airlines Summer Travel Deals
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$224 Chicago, Illinois Chicago Savings! Book at Sofitel Chicago Water Tower Fr $224+/Nt
Expedia
$207 Chicago, Illinois Southwest Airlines Summer Travel Deals
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$178 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $178+/Nt
Save with Expedia, $31/night less
$99 Chicago, Illinois Southwest Airlines Summer Travel Deals
DealBase.com
$243 Chicago, Illinois Book in Chicago: Save at the Swissotel Chicago in May Fr $243+/Nt
Save with Expedia, $27/night less
$182 Chicago, Illinois Southwest Airlines Autumn Escape Sale
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$189 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $189+/Nt
Expedia
$59 Chicago, Illinois Frontier Airlines Travel Deals
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$236 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $236+/Nt
Expedia
$137 Chicago, Illinois Southwest Airlines Autumn Escape Sale
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$194 Chicago, Illinois Book 3 Nts in Chicago this May Fr $194+/Nt
Expedia
$278 Chicago, Illinois United Airlines Weekend Specials for 5/29/15
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$136 Chicago, Illinois Book 3.5-Star Central Loop in Chicago Fr $136+/Nt
Save with Expedia, $33/night less
$207 Chicago, Illinois Southwest Airlines Summer Travel Deals
DealBase.com
$195 Chicago, Illinois $195 & Up: Residence Inn Chicago Downtown 3-Star Hotel in Chicago
Expedia
$92 Chicago, Illinois Southwest Airlines Autumn Escape Sale
DealBase.com
$173 Chicago, Illinois Small budget: Stay in Chicago this May Fr $173+/Nt
Expedia
$211 Chicago, Illinois Southwest Airlines Summer Travel Deals
DealBase.com
$229 Chicago, Illinois May deal: The Westin Michigan Avenue Chicago Fr $229+/Nt
Expedia
$119 Chicago, Illinois Southwest Airlines Autumn Escape Sale
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$198 Chicago, Illinois Chicago Downtown, Autograph Collection in May: $198 & Up
Expedia
$251 Chicago, Illinois Southwest Airlines Mexico and Caribbean Sale
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$156 Chicago, Illinois Book 3-Star Holiday Inn Express Cass Fr $156+/Nt
Expedia
$150 Chicago, Illinois Southwest Airlines Autumn Escape Sale
DealBase.com
$207 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $207+/Nt
Save with Expedia, $22/night less
$128 Chicago, Illinois Southwest Airlines Autumn Escape Sale
DealBase.com
$366 Chicago, Illinois Waldorf Astoria Chicago on Sale: Book 3 Nts in May Fr $366+/Nt
Expedia
$89+ Chicago, Illinois Chicago Hotel Deals For As Low As $89/nt!
Jetsetter
$230 Chicago, Illinois The Blackstone A Renaissance in May: $230 & Up
Expedia
$226 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $226+/Nt
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$243 Chicago, Illinois Chicago Savings! Book at Buckingham Athletic Club Fr $243+/Nt
Expedia
$156 Chicago, Illinois Book the Holiday Inn Chicago Downtown 3 Nts in May Fr $156+/Nt
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$169 Chicago, Illinois Chicago Savings! Book at Hyatt Regency Chicago Fr $169+/Nt
Expedia
$204 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in May: $204 & Up
Expedia
$152 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $152+/Nt
Expedia
$109 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $109+/Nt
Save with Expedia, $19/night less
$168 Chicago, Illinois Small budget: Stay in Chicago this May Fr $168+/Nt
Expedia
$405 Chicago, Illinois Save Big This May! Book 3 Nts at Four Seasons Chicago Fr $405+/Nt
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$129 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $129+/Nt
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$179 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $179+/Nt
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$220 Chicago, Illinois Save Big This May! Book 3 Nts at Radisson Blu Aqua Fr $220+/Nt
Expedia
$299 Chicago, Illinois May deal: Chicago Marriott at Medical District/UIC Fr $299+/Nt
Expedia
$190 Chicago, Illinois Save in Chicago: Book 3 Nts in May Fr $190+/Nt
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$195 Chicago, Illinois The Palmer House Hilton in May: $195 & Up
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$149 Chicago, Illinois Book in Chicago: Save at the Congress Plaza in May Fr $149+/Nt
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$239 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $239+/Nt
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$219 Chicago, Illinois Book in Chicago: Save this May Fr $219+/Nt
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$190 Chicago, Illinois Hyatt Chicago Magnificent Mile in May: $190 & Up
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$209 Chicago, Illinois May deal: La Quinta Inn & Suites Chicago Downtown Fr $209+/Nt
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$330 Chicago, Illinois Small budget: Stay in Chicago this May Fr $330+/Nt
Save with Expedia, $82/night less
$171 Chicago, Illinois Book 3-Star ACME Company Chicago in Chicago Fr $171+/Nt
Save with Expedia, $30/night less
$225 Chicago, Illinois Chicago Savings! Book 3 Nts in May Fr $225+/Nt
Save with Expedia, $121/night less
$198 Chicago, Illinois Save at 4-Star Fairmont Chicago Millennium Park: $198 & Up in May
Save with Expedia, $35/night less
$224 Chicago, Illinois Save in Chicago: Book 3 Nts in May at Hilton Chicago Fr $224+/Nt
Expedia
$246 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $246+/Nt
Expedia
$194 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $194+/Nt
Expedia
$162 Chicago, Illinois Save at 3-Star BEST WESTERN River North: $162 & Up in May
Expedia
$253 Chicago, Illinois May deal: Chicago Marriott Downtown Magnificent Mile Fr $253+/Nt
Expedia
$184 Chicago, Illinois The Whitehall on Sale: Book 3 Nts in May Fr $184+/Nt
Save with Expedia, $25/night less
$179 Chicago, Illinois $179 & Up: Hyatt Regency McCormick Place 4-Star Hotel in Chicago
Expedia
$173 Chicago, Illinois Small budget: Stay in Chicago this May Fr $173+/Nt
Expedia
$84 Chicago, Illinois Book 3 Nts in Chicago this May Fr $84+/Nt
Expedia
$226 Chicago, Illinois Comfort Suites Michigan Avenue in May: $226 & Up
Expedia
$198 Chicago, Illinois Book in Chicago: Save at the Hard Rock Chicago in May Fr $198+/Nt
Save with Expedia, $35/night less
$206 Chicago, Illinois May deal: Courtyard Chicago Downtown River North Fr $206+/Nt
Expedia
$199 Chicago, Illinois Embassy Suites Chicago Downtown in May: $199 & Up
Expedia
$144 Chicago, Illinois Save Big This May! Book 3 Nts in Chicago Fr $144+/Nt
Expedia
$299 Chicago, Illinois Chicago Savings! Book at Conrad Chicago Fr $299+/Nt
Expedia
$133 Chicago, Illinois May deal: The Tremont Chicago at Magnificent Mile Fr $133+/Nt
Expedia
$175 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $175+/Nt
Expedia
$415 Chicago, Illinois Book in Chicago: Save this May Fr $415+/Nt
Expedia
PRICEDESTINATIONDEAL
$79 Philadelphia, Pennsylvania Frontier Airlines Travel Deals
DealBase.com
$187 Philadelphia, Pennsylvania Cheap Flights from Las Vegas
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$138 Philadelphia, Pennsylvania Cheap Flights from Chicago
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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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