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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$10 Chicago, Illinois Cheap Car Rentals in Chicago Fr $10/Day
CarRentals.com
$160 Chicago, Illinois Chicago Savings! Book at The James Chicago Fr $160+/Nt
Save with Expedia, $106/night less
$186+ Chicago, Illinois Save with United! Low Fares to Chicago Starting at $186
DealBase.com
$149 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $149+/Nt
Expedia
$138+ Chicago, Illinois Save with United! Low Fares to Chicago Starting at $138
DealBase.com
$99 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $99+/Nt
Expedia
$178+ Chicago, Illinois Travel to Chicago for Less: 23 Routes From $178
DealBase.com
$244 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $244+/Nt
Save with Expedia, $131/night less
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$119 Chicago, Illinois Apr deal: Hilton Suites Chicago/Magnificent Mile Fr $119+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$126 Chicago, Illinois Special deal: 3.5-Star River Fr $126+/Nt
Expedia
$167 Chicago, Illinois Book Now & Save! Chicago Fr $167+/Nt
Travelocity
$128 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr at Blake Chicago Fr $128+/Nt
Expedia
$393 Chicago, Illinois Super Sale! 1 Nts Fairmont Chicago Millennium Park + Air Fr $393
Travelocity
$119 Chicago, Illinois Book 3.5-Star Embassy Suites Chicago Downtown Fr $119+/Nt
Expedia
$493 Chicago, Illinois Chicago on Sale! 3 Nts + Air as Low as $493
Travelocity
$104 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $104+/Nt
Expedia
$105 Chicago, Illinois Visit Chicago for Less: Hotels Fr $105+/Nt
Travelocity
$149 Chicago, Illinois Apr deal: Hyatt Chicago Magnificent Mile Fr $149+/Nt
Expedia
$109 Chicago, Illinois Book Now & Save! Chicago Fr $109+/Nt
Travelocity
$334 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $334+/Nt
Expedia
$566 Chicago, Illinois Look no Further! Chicago 3 Nts + Air as Low as $566
Travelocity
$118 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $118+/Nt
Expedia
$140 Chicago, Illinois Book Now & Save! Chicago Fr $140+/Nt
Travelocity
$209 Chicago, Illinois Chicago Marriott Downtown Magnificent Mile in Apr: $209 & Up
Expedia
$584 Chicago, Illinois Unbelievable Price! 3 Nts Swissotel Chicago + Air Fr $584
Travelocity
$133 Chicago, Illinois Save at 3-Star Chicago's Essex Inn: $133 & Up in Apr
Save with Expedia, $33/night less
$353 Chicago, Illinois Look no Further! Chicago 1 Nts + Air as Low as $353
Travelocity
$99 Chicago, Illinois Book 3-Star Comfort Suites Michigan Avenue Fr $99+/Nt
Expedia
$341 Chicago, Illinois Super Sale! 1 Nts Hyatt Regency McCormick Place + Air Fr $341
Travelocity
$124 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $124+/Nt
Expedia
$134 Chicago, Illinois Visit Chicago for Less: Hotels Fr $134+/Nt
Travelocity
$109 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $109+/Nt
Expedia
$335 Chicago, Illinois Look no Further! Chicago 1 Nts + Air as Low as $335
Travelocity
$110 Chicago, Illinois Book 4-Star Millennium Knickerbocker Chicago Fr $110+/Nt
Save with Expedia, $36/night less
$402 Chicago, Illinois Look no Further! Chicago 1 Nts + Air as Low as $402
Travelocity
$368 Chicago, Illinois $368 & Up: The Peninsula Chicago 5-Star Hotel in Chicago
Expedia
$401 Chicago, Illinois Up to 9% OFF on Chicago 3 Nts Htl + Air Fr $401
Travelocity
$124 Chicago, Illinois The Westin Michigan Avenue Chicago in Apr: $124 & Up
Expedia
$299 Chicago, Illinois Last Minute Vacation Sale! 3 Nts Chicago + Air Fr $299
Travelocity
$90 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $90+/Nt
Expedia
$123 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $123+/Nt
Expedia
$102 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at Raffaello Fr $102+/Nt
Save with Expedia, $55/night less
$93 Chicago, Illinois Book 3-Star The Tremont Chicago at Magnificent Mile Fr $93+/Nt
Expedia
$167 Chicago, Illinois Book the The Westin Chicago River North 3 Nts in Apr Fr $167+/Nt
Expedia
$169 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $169+/Nt
Expedia
$109 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $109+/Nt
Expedia
$88 Chicago, Illinois Apr deal: Chicago South Loop Fr $88+/Nt
Save with Expedia, $21/night less
$155 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at Conrad Chicago Fr $155+/Nt
Expedia
$175 Chicago, Illinois Special deal: 4-Star theWit - A DoubleTree by Hilton Fr $175+/Nt
Expedia
$89 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $89+/Nt
Expedia
$173 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at dana and spa Fr $173+/Nt
Expedia
$170 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $170+/Nt
Save with Expedia, $29/night less
$139 Chicago, Illinois Chicago Savings! Book at The Blackstone A Renaissance Fr $139+/Nt
Expedia
$153 Chicago, Illinois Book 3.5-Star Kinzie in Chicago Fr $153+/Nt
Save with Expedia, $75/night less
$119 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr Fr $119+/Nt
Expedia
$107 Chicago, Illinois ACME Company Chicago on Sale: Book 3 Nts in Apr Fr $107+/Nt
Save with Expedia, $19/night less
$279 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $279+/Nt
Expedia
$124 Chicago, Illinois Book in Chicago: Save this Apr Fr $124+/Nt
Expedia
$140 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $140+/Nt
Expedia
$169 Chicago, Illinois Chicago Savings! Book at Hyatt Regency Chicago Fr $169+/Nt
Expedia
$89 Chicago, Illinois Book the BEST WESTERN Grant Park 3 Nts in Apr Fr $89+/Nt
Expedia
$162 Chicago, Illinois Chicago Downtown, Autograph Collection in Apr: $162 & Up
Save with Expedia, $107/night less
$124 Chicago, Illinois Book 3.5-Star Crowne Plaza Chicago - The Metro Fr $124+/Nt
Expedia
$116 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $116+/Nt
Save with Expedia, $21/night less
$159 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $159+/Nt
Expedia
$89 Chicago, Illinois Save at 3-Star Congress Plaza: $89 & Up in Apr
Expedia
$114 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago Downtown Fr $114+/Nt
Expedia
$70 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $70+/Nt
Expedia
$272 Chicago, Illinois Book 5-Star Trump International & Tower Chicago Fr $272+/Nt
Save with Expedia, $90/night less
$129 Chicago, Illinois Small budget: Book JW Marriott Chicago 3 Nts in Apr Fr $129+/Nt
Expedia
$129 Chicago, Illinois Apr deal: Hampton Majestic Chicago Theatre District Fr $129+/Nt
Expedia
$195 Chicago, Illinois Book 4-Star Swissotel Chicago Fr $195+/Nt
Save with Expedia, $48/night less
$119 Chicago, Illinois Chicago Savings! Book at Buckingham Athletic Club Fr $119+/Nt
Expedia
$160 Chicago, Illinois Apr deal: Courtyard Chicago Downtown/Magnificent Mile Fr $160+/Nt
Expedia
$162 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at Omni Chicago Fr $162+/Nt
Save with Expedia, $17/night less
$95 Chicago, Illinois Book 3.5-Star Indigo Chicago Downtown Gold Coast Fr $95+/Nt
Expedia
$118 Chicago, Illinois Book the The Whitehall 3 Nts in Apr Fr $118+/Nt
Save with Expedia, $58/night less
$168 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $168+/Nt
Save with Expedia, $41/night less
$143 Chicago, Illinois Chicago Savings! Book at W Chicago Lakeshore Fr $143+/Nt
Expedia
$146 Chicago, Illinois Book 4.5-Star Sofitel Chicago Water Tower in Chicago Fr $146+/Nt
Save with Expedia, $36/night less
$91 Chicago, Illinois Book in Chicago: Save this Apr Fr $91+/Nt
Save with Expedia, $48/night less
$139 Chicago, Illinois Chicago Savings! Book 3 Nts in Apr at The Silversmith Fr $139+/Nt
Expedia
$150 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $150+/Nt
Expedia
$171 Chicago, Illinois Small budget: Stay in Chicago this Apr Fr $171+/Nt
Expedia
$86 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $86+/Nt
Expedia
$120 Chicago, Illinois Save Big This Apr! Book 3 Nts in Chicago Fr $120+/Nt
Save with Expedia, $39/night less
$213 Chicago, Illinois Book 4-Star Hard Rock Chicago in Chicago Fr $213+/Nt
Expedia
$139 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $139+/Nt
Expedia
$93 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $93+/Nt
Expedia
$200 Chicago, Illinois $200 & Up: Burnham - a Kimpton 4-Star Hotel in Chicago
Save with Expedia, $50/night less
$123 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $123+/Nt
Expedia
$116 Chicago, Illinois $116 & Up: Felix 4-Star Hotel in Chicago
Save with Expedia, $21/night less
$116 Chicago, Illinois Save Big This Apr! Book 3 Nts at The Drake Fr $116+/Nt
Expedia
$159 Chicago, Illinois Apr deal: Courtyard by Marriott Chicago Downtown Fr $159+/Nt
Expedia
$156 Chicago, Illinois Save in Chicago: Book 3 Nts in Apr Fr $156+/Nt
Expedia
$155 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $155+/Nt
Save with Expedia, $24/night less
$195 Chicago, Illinois Book 3 Nts in Chicago this Apr Fr $195+/Nt
Expedia
$159 Chicago, Illinois Book in Chicago: Save this Apr Fr $159+/Nt
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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