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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$71+ Chicago, Illinois 3-Star Chicago Hotels from $71/night
trivago
$155 Chicago, Illinois Exclusive Offer! Now Over 50% OFF Luxury Rooms!
BookIt.com
$79 Chicago, Illinois Chicago Savings! Book at Hyatt Regency McCormick Place Fr $79+/Nt
Expedia
$118 Chicago, Illinois 35% OFF Premiere Eco-Friendly Hotel + FREE Wi-Fi!
BookIt.com
35% Off Chicago, Illinois Thompson Chicago: Save 35% on Deluxe 2-Nt Stay
Luxury Link
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$550 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $550
Expedia
$522 Chicago, Illinois Great Rates in Chicago + Breakfast!
DealBase.com
$923 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $923
Expedia
$390 Chicago, Illinois US Airways Catch a Wave in Florida Promotion
DealBase.com
$536 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $536
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$716 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $716
Expedia
$958 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $958
Expedia
$115 Chicago, Illinois Save Big This Jul! Book 3 Nts in Chicago Fr $115+/Nt
Expedia
$112 Chicago, Illinois Small budget: Stay in Chicago this Jul Fr $112+/Nt
Expedia
$119 Chicago, Illinois Book 4-Star Hilton Chicago O'Hare Airport Fr $119+/Nt
Expedia
$240 Chicago, Illinois Jul deal: Palomar Chicago, a Kimpton Fr $240+/Nt
Expedia
$216 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $216+/Nt
Expedia
$153 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $153+/Nt
Save with Expedia, $26/night less
$95 Chicago, Illinois Jul deal: The Tremont Chicago at Magnificent Mile Fr $95+/Nt
Expedia
$174 Chicago, Illinois Small budget: Stay in Chicago this Jul Fr $174+/Nt
Expedia
$163 Chicago, Illinois Jul deal: River Fr $163+/Nt
Expedia
$141 Chicago, Illinois Jul deal: The Silversmith Fr $141+/Nt
Save with Expedia, $25/night less
$150 Chicago, Illinois Chicago Savings! Book at BEST WESTERN River North Fr $150+/Nt
Expedia
$159 Chicago, Illinois Book 3.5-Star Buckingham Athletic Club Fr $159+/Nt
Expedia
$196 Chicago, Illinois Small budget: Stay in Chicago this Jul Fr $196+/Nt
Expedia
$1,171 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $1,171
Expedia
$199 Chicago, Illinois Book in Chicago: Save this Jul Fr $199+/Nt
Expedia
$158 Chicago, Illinois Jul deal: Chicago's Essex Inn Fr $158+/Nt
Save with Expedia, $28/night less
$116 Chicago, Illinois Special deal: 4-Star Felix Fr $116+/Nt
Save with Expedia, $21/night less
$229 Chicago, Illinois Book 4-Star JW Marriott Chicago in Chicago Fr $229+/Nt
Expedia
$184 Chicago, Illinois Small budget: Stay in Chicago this Jul Fr $184+/Nt
Expedia
$149 Chicago, Illinois Book in Chicago: Save this Jul Fr $149+/Nt
Expedia
$114 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $114+/Nt
Expedia
$143 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $143+/Nt
Expedia
$129 Chicago, Illinois Book 3-Star Holiday Inn Express Cass in Chicago Fr $129+/Nt
Expedia
$103 Chicago, Illinois Book in Chicago: Save this Jul Fr $103+/Nt
Expedia
$203 Chicago, Illinois W Chicago Lakeshore on Sale: Book 3 Nts in Jul Fr $203+/Nt
Expedia
$185 Chicago, Illinois Book 4-Star theWit - A DoubleTree by Hilton Fr $185+/Nt
Expedia
$813 Chicago, Illinois Save at 5-Star Hotel: 3 Nts + Air to Chicago Fr $813
Expedia
$130 Chicago, Illinois Book in Chicago: Save this Jul Fr $130+/Nt
Expedia
$179 Chicago, Illinois Hampton Majestic Chicago Theatre District in Jul: $179 & Up
Expedia
$129 Chicago, Illinois Save in Chicago: Book 3 Nts in Jul at Central Loop Fr $129+/Nt
Expedia
$199 Chicago, Illinois Special deal: 4-Star The Blackstone A Renaissance Fr $199+/Nt
Expedia
$1,565 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,565
Expedia
$175 Chicago, Illinois W Chicago - City Center in Jul: $175 & Up
Expedia
$126 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $126+/Nt
Expedia
$205 Chicago, Illinois Small budget: Stay in Chicago this Jul Fr $205+/Nt
Expedia
$327 Chicago, Illinois Chicago Savings! Book at Waldorf Astoria Chicago Fr $327+/Nt
Expedia
$199 Chicago, Illinois Omni Chicago in Jul: $199 & Up
Expedia
$197 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $197+/Nt
Expedia
$134 Chicago, Illinois Holiday Inn Chicago Mart Plaza River North in Jul: $134 & Up
Expedia
$169 Chicago, Illinois Save in Chicago: Book 3 Nts in Jul Fr $169+/Nt
Expedia
$169 Chicago, Illinois Kinzie on Sale: Book 3 Nts in Jul Fr $169+/Nt
Expedia
$316 Chicago, Illinois Jul deal: Trump International & Tower Chicago Fr $316+/Nt
Save with Expedia, $79/night less
$229 Chicago, Illinois Save Big This Jul! Book 3 Nts in Chicago Fr $229+/Nt
Expedia
$110 Chicago, Illinois BEST WESTERN Grant Park on Sale: Book 3 Nts in Jul Fr $110+/Nt
Save with Expedia, $27/night less
$259 Chicago, Illinois Small budget: Book Renaissance Chicago 3 Nts in Jul Fr $259+/Nt
Expedia
$173 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $173+/Nt
Expedia
$143 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $143+/Nt
Expedia
$160 Chicago, Illinois The Westin Michigan Avenue Chicago in Jul: $160 & Up
Expedia
$187 Chicago, Illinois Chicago Savings! Book at Swissotel Chicago Fr $187+/Nt
Save with Expedia, $46/night less
$148 Chicago, Illinois Save Big This Jul! Book 3 Nts in Chicago Fr $148+/Nt
Save with Expedia, $37/night less
$189 Chicago, Illinois Book in Chicago: Save at the The Drake in Jul Fr $189+/Nt
Expedia
$161 Chicago, Illinois Book in Chicago: Save this Jul Fr $161+/Nt
Expedia
$123 Chicago, Illinois Doubletree by Hilton Chicago Magnificent Mile in Jul: $123 & Up
Expedia
$126 Chicago, Illinois Special deal: 3-Star Holiday Inn Chicago Downtown Fr $126+/Nt
Expedia
$163 Chicago, Illinois Chicago Savings! Book at MileNorth, A Chicago Fr $163+/Nt
Expedia
$129 Chicago, Illinois Save at 4-Star Warwick Allerton Chicago: $129 & Up in Jul
Save with Expedia, $43/night less
$179 Chicago, Illinois Save in Chicago: Book 3 Nts in Jul Fr $179+/Nt
Expedia
$164 Chicago, Illinois $164 & Up: The James Chicago 4.5-Star Hotel in Chicago
Save with Expedia, $29/night less
$147 Chicago, Illinois Book 4-Star The Whitehall Fr $147+/Nt
Save with Expedia, $48/night less
$120 Chicago, Illinois Crowne Plaza Chicago - The Metro in Jul: $120 & Up
Save with Expedia, $39/night less
$130 Chicago, Illinois Save Big This Jul! Book 3 Nts in Chicago Fr $130+/Nt
Expedia
$180 Chicago, Illinois Book in Chicago: Save this Jul Fr $180+/Nt
Expedia
$193 Chicago, Illinois Book the Sheraton Chicago and Towers 3 Nts in Jul Fr $193+/Nt
Expedia
$179 Chicago, Illinois Special deal: 4-Star Hard Rock Chicago Fr $179+/Nt
Expedia
$119 Chicago, Illinois Chicago Savings! Book at The Palmer House Hilton Fr $119+/Nt
Expedia
$169 Chicago, Illinois Small budget: Stay in Chicago this Jul Fr $169+/Nt
Expedia
$110 Chicago, Illinois Book in Chicago: Save this Jul Fr $110+/Nt
Save with Expedia, $19/night less
$225 Chicago, Illinois Chicago Savings! Book at Conrad Chicago Fr $225+/Nt
Expedia
$98 Chicago, Illinois Jul deal: Indigo Chicago Downtown Gold Coast Fr $98+/Nt
Expedia
$156 Chicago, Illinois Save Big This Jul! Book 3 Nts in Chicago Fr $156+/Nt
Expedia
$178 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $178+/Nt
Expedia
$147 Chicago, Illinois Special deal: 4-Star dana and spa Fr $147+/Nt
Save with Expedia, $26/night less
$171 Chicago, Illinois Book 3 Nts in Chicago this Jul Fr $171+/Nt
Expedia
$127 Chicago, Illinois Small budget: Book Chicago South Loop 3 Nts in Jul Fr $127+/Nt
Save with Expedia, $22/night less
$114 Chicago, Illinois Small budget: Stay in Chicago this Jul Fr $114+/Nt
Expedia
$183 Chicago, Illinois Small budget: Stay in Chicago this Jul Fr $183+/Nt
Expedia
$169 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul Fr $169+/Nt
Expedia
$180 Chicago, Illinois Courtyard Chicago Downtown/Magnificent Mile in Jul: $180 & Up
Expedia
$149 Chicago, Illinois Chicago Savings! Book 3 Nts in Jul at Hilton Chicago Fr $149+/Nt
Expedia
$102 Tinley Park, Illinois Jul deal: Hampton Inn Chicago / Tinley Park Fr $102+/Nt
Expedia
$79 Oakbrook Terrace, Illinois Hilton Garden Inn Oakbrook Terrace in Jul: $79 & Up
Expedia
$102 Rosemont, Illinois Book the BEST WESTERN at O'Hare 3 Nts in Jul Fr $102+/Nt
Save with Expedia, $18/night less
$89 Itasca, Illinois Book 3-Star Hyatt Place Itasca in Itasca Fr $89+/Nt
Expedia
$75 Arlington Heights, Illinois Arlington Heights Savings! Book 3 Nts in Jul Fr $75+/Nt
Save with Expedia, $25/night less
$126 Skokie, Illinois Jul deal: DoubleTree by Hilton Chicago North Shore Fr $126+/Nt
Expedia
$66 Schiller Park, Illinois Save Big This Jul! Book 3 Nts at O'Hare Inn & Suites Fr $66+/Nt
Save with Expedia, $43/night less
PRICEDESTINATIONDEAL
$285 Newark, New Jersey Cheap Flights from Dallas
DealBase.com
$117 Newark, New Jersey Cheap Flights from Boston
DealBase.com
$254 Newark, New Jersey Cheap Flights from Atlanta
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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