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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$297 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $297+/Nt
Save with Expedia, $98/night less
$138+ Chicago, Illinois Save with United! Low Fares to Chicago Starting at $138
DealBase.com
$139 Chicago, Illinois Book in Chicago: Save this Apr Fr $139+/Nt
Expedia
$178+ Chicago, Illinois Travel to Chicago for Less: 23 Routes From $178
DealBase.com
$268 Chicago, Illinois Chicago Savings! Book at Park Hyatt Chicago Fr $268+/Nt
Expedia
$186+ Chicago, Illinois Save with United! Low Fares to Chicago Starting at $186
DealBase.com
$107 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $107+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$146 Chicago, Illinois Apr deal: Crowne Plaza Chicago - The Metro Fr $146+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$180 Chicago, Illinois Residence Inn Chicago Downtown / River North in Apr: $180 & Up
Expedia
$299 Chicago, Illinois Chicago on Sale! 3 Nts + Air as Low as $299
Travelocity
$169 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $169+/Nt
Expedia
$335 Chicago, Illinois Super Savings on Chicago 1 Nts Htl + Air Fr $335
Travelocity
$189 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $189+/Nt
Expedia
$353 Chicago, Illinois Top Vacation Sale! 1 Nts + Air as Low as $353
Travelocity
$225 Chicago, Illinois Book in Chicago: Save this Apr Fr $225+/Nt
Expedia
$401 Chicago, Illinois Last Minute Vacation Sale! 3 Nts Chicago + Air Fr $401
Travelocity
$166 Chicago, Illinois Apr deal: Homewood Suites by Hilton Chicago Downtown Fr $166+/Nt
Expedia
$109 Chicago, Illinois Visit Chicago for Less: Hotels Fr $109+/Nt
Travelocity
$182 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $182+/Nt
Save with Expedia, $27/night less
$140 Chicago, Illinois Book Now & Save! Chicago Fr $140+/Nt
Travelocity
$217 Chicago, Illinois Comfort Suites Michigan Avenue in Apr: $217 & Up
Expedia
$167 Chicago, Illinois Look no Further! Chicago Hotels Fr $167+/Nt
Travelocity
$189 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at The Drake Fr $189+/Nt
Expedia
$341 Chicago, Illinois Super Sale! 1 Nts Hyatt Regency McCormick Place + Air Fr $341
Travelocity
$99 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $99+/Nt
Expedia
$592 Chicago, Illinois 3% OFF Fairmont Chicago Millennium Park! 3 Nts + Air Fr $592
Travelocity
$139 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $139+/Nt
Expedia
$493 Chicago, Illinois Up to 8% OFF on Chicago 3 Nts Htl + Air Fr $493
Travelocity
$125 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $125+/Nt
Save with Expedia, $31/night less
$402 Chicago, Illinois Up to 3% OFF on Chicago 1 Nts Htl + Air Fr $402
Travelocity
$303 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $303+/Nt
Expedia
$566 Chicago, Illinois Up to 3% OFF on Chicago 3 Nts Htl + Air Fr $566
Travelocity
$133 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $133+/Nt
Expedia
$584 Chicago, Illinois 5% OFF Swissotel Chicago! 3 Nts + Air Fr $584
Travelocity
$104 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $104+/Nt
Expedia
$9 Chicago, Illinois Cheap Car Rentals in Chicago Fr $9/Day
CarRentals.com
$150 Chicago, Illinois La Quinta Inn & Suites Chicago Downtown in Apr: $150 & Up
Expedia
$134 Chicago, Illinois Visit Chicago for Less: Hotels Fr $134+/Nt
Travelocity
$126 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $126+/Nt
Expedia
$105 Chicago, Illinois Visit Chicago for Less: Hotels Fr $105+/Nt
Travelocity
$235 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $235+/Nt
Expedia
$245 Chicago, Illinois Special deal: 4-Star Radisson Blu Aqua Fr $245+/Nt
Expedia
$170 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $170+/Nt
Save with Expedia, $29/night less
$172 Chicago, Illinois Save at 4-Star The Westin Chicago River North: $172 & Up in Apr
Expedia
$170 Chicago, Illinois Hyatt Chicago Magnificent Mile in Apr: $170 & Up
Expedia
$191 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $191+/Nt
Save with Expedia, $94/night less
$200 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $200+/Nt
Save with Expedia, $50/night less
$179 Chicago, Illinois Book 4-Star The Blackstone A Renaissance in Chicago Fr $179+/Nt
Expedia
$179 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $179+/Nt
Expedia
$119 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport in Chicago Fr $119+/Nt
Expedia
$129 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $129+/Nt
Expedia
$159 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $159+/Nt
Expedia
$164 Chicago, Illinois Book 3.5-Star Embassy Suites Chicago Downtown Fr $164+/Nt
Expedia
$180 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $180+/Nt
Expedia
$156 Chicago, Illinois The Palmer House Hilton in Apr: $156 & Up
Expedia
$175 Chicago, Illinois theWit - A DoubleTree by Hilton in Apr: $175 & Up
Expedia
$119 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $119+/Nt
Save with Expedia, $20/night less
$243 Chicago, Illinois Book in Chicago: Save this Apr Fr $243+/Nt
Expedia
$120 Chicago, Illinois Book 3-Star Congress Plaza Fr $120+/Nt
Expedia
$359 Chicago, Illinois Chicago Savings! Book at The Peninsula Chicago Fr $359+/Nt
Expedia
$170 Chicago, Illinois Wyndham Grand Chicago Riverfront in Apr: $170 & Up
Save with Expedia, $29/night less
$80 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $80+/Nt
Expedia
$179 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $179+/Nt
Expedia
$136 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $136+/Nt
Expedia
$180 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at Omni Chicago Fr $180+/Nt
Save with Expedia, $19/night less
$189 Chicago, Illinois Apr deal: dana and spa Fr $189+/Nt
Expedia
$109 Chicago, Illinois Apr deal: Central Loop Fr $109+/Nt
Expedia
$277 Chicago, Illinois Book the Four Seasons Chicago 3 Nts in Apr Fr $277+/Nt
Save with Expedia, $138/night less
$244 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $244+/Nt
Save with Expedia, $121/night less
$109 Chicago, Illinois Holiday Inn Express Cass in Apr: $109 & Up
Expedia
$192 Chicago, Illinois Book 4-Star W Chicago Lakeshore in Chicago Fr $192+/Nt
Expedia
$229 Chicago, Illinois Apr deal: Chicago Marriott Downtown Magnificent Mile Fr $229+/Nt
Expedia
$192 Chicago, Illinois $192 & Up: Monaco Chicago - a Kimpton 4-Star Hotel in Chicago
Save with Expedia, $48/night less
$199 Chicago, Illinois Special deal: 4-Star MileNorth, A Chicago Fr $199+/Nt
Expedia
$104 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $104+/Nt
Expedia
$128 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $128+/Nt
Save with Expedia, $32/night less
$161 Chicago, Illinois Apr deal: Chicago Marriott at Medical District/UIC Fr $161+/Nt
Expedia
$142 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $142+/Nt
Expedia
$137 Chicago, Illinois Book in Chicago: Save this Apr Fr $137+/Nt
Save with Expedia, $74/night less
$106 Chicago, Illinois Book in Chicago: Save at the Blake Chicago in Apr Fr $106+/Nt
Expedia
$179 Chicago, Illinois Apr deal: Hilton Suites Chicago/Magnificent Mile Fr $179+/Nt
Expedia
$303 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $303+/Nt
Expedia
$156 Chicago, Illinois Apr deal: Buckingham Athletic Club Fr $156+/Nt
Expedia
$127 Chicago, Illinois $127 & Up: Chicago South Loop 3-Star Hotel in Chicago
Save with Expedia, $22/night less
$105 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Apr: $105 & Up
Expedia
$141 Chicago, Illinois Book in Chicago: Save this Apr Fr $141+/Nt
Expedia
$206 Chicago, Illinois Chicago Savings! Book at Sheraton Chicago and Towers Fr $206+/Nt
Expedia
$171 Chicago, Illinois Apr deal: Sofitel Chicago Water Tower Fr $171+/Nt
Expedia
$192 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $192+/Nt
Save with Expedia, $20/night less
$179 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $179+/Nt
Expedia
$127 Chicago, Illinois Book the BEST WESTERN River North 3 Nts in Apr Fr $127+/Nt
Expedia
$361 Chicago, Illinois Save at 5-Star Waldorf Astoria Chicago: $361 & Up in Apr
Expedia
$211 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $211+/Nt
Save with Expedia, $52/night less
$167 Chicago, Illinois Book 4-Star Raffaello in Chicago Fr $167+/Nt
Save with Expedia, $89/night less
$102 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $102+/Nt
Expedia
$219 Chicago, Illinois Book 3-Star Hampton Majestic Chicago Theatre District Fr $219+/Nt
Expedia
$196 Chicago, Illinois InterContinental Chicago in Apr: $196 & Up
Expedia
$117 Chicago, Illinois BEST WESTERN Grant Park in Apr: $117 & Up
Expedia
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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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