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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$179 Chicago, Illinois Book 3 Nts in Chicago this Aug Fr $179+/Nt
Expedia
$136 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $136+/Nt
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$196 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $196+/Nt
Expedia
$183 Chicago, Illinois Book in Chicago: Save this Aug Fr $183+/Nt
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$279 Chicago, Illinois Aug deal: Renaissance Chicago Fr $279+/Nt
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$179 Chicago, Illinois Save Big This Aug! Book 3 Nts at W Chicago Lakeshore Fr $179+/Nt
Expedia
$203 Chicago, Illinois Chicago Savings! Book at AC Chicago Downtown Fr $203+/Nt
Expedia
$149 Chicago, Illinois Book 4-Star Hyatt Regency Chicago Fr $149+/Nt
Expedia
$259 Chicago, Illinois Book 4.5-Star Conrad Chicago Fr $259+/Nt
Expedia
$159 Chicago, Illinois Save Big This Aug! Book 3 Nts in Chicago Fr $159+/Nt
Expedia
$203 Chicago, Illinois The Blackstone A Renaissance in Aug: $203 & Up
Expedia
$150 Chicago, Illinois Save at 3.5-Star Blake Chicago: $150 & Up in Aug
Expedia
$199 Chicago, Illinois Chicago Savings! Book 3 Nts in Aug Fr $199+/Nt
Expedia
$166 Chicago, Illinois Aug deal: Hilton Chicago O'Hare Airport Fr $166+/Nt
Expedia
$349 Chicago, Illinois Save in Chicago: Book 3 Nts in Aug Fr $349+/Nt
Expedia
$149 Chicago, Illinois Special deal: 4-Star Hilton Chicago Fr $149+/Nt
Expedia
$199 Chicago, Illinois Save Big This Aug! Book 3 Nts at The Drake Fr $199+/Nt
Expedia
$407 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $407
Expedia
$1,162 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,162
Expedia
$853 Chicago, Illinois Chicago 5-Star Hotel Sale! 3 Nts + Air Fr $853
Expedia
$1,032 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,032
Expedia
$1,109 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,109
Expedia
$958 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $958
Expedia
$691 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $691
Expedia
$1,169 Chicago, Illinois 5-Star Chicago Sale! 3 Nts + Air Fr $1,169
Expedia
$773 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $773
Expedia
$35+ Oak Park, Illinois Oak Park Vacation Rental Deals From $35
Tripping
$88 Burbank, Illinois Burbank Savings! Book 3 Nts in Aug Fr $88+/Nt
Expedia
$50+ Evanston, Illinois Evanston Vacation Rental Deals From $50
Tripping
$153 Bedford Park, Illinois Hilton Garden Inn Chicago Midway Airport in Aug: $153 & Up
Expedia
$59+ Elmhurst, Illinois Elmhurst Vacation Rental Deals From $59
Tripping
$136 Bedford Park, Illinois Save Big This Aug! Book 3 Nts in Bedford Park Fr $136+/Nt
Expedia
$43+ Downers Grove, Illinois Downers Grove Vacation Rental Deals From $43
Tripping
$78 Bridgeview, Illinois Save in Bridgeview: Book 3 Nts in Aug Fr $78+/Nt
Expedia
$93 Westchester, Illinois Save Big This Aug! Book 3 Nts in Westchester Fr $93+/Nt
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$110 Countryside, Illinois Countryside Savings! Book 3 Nts in Aug Fr $110+/Nt
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$106 Schiller Park, Illinois Small budget: Stay in Schiller Park this Aug Fr $106+/Nt
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$119 Schiller Park, Illinois Book in Schiller Park: Save this Aug Fr $119+/Nt
Expedia
$101 Skokie, Illinois Aug deal: DoubleTree by Hilton Chicago North Shore Fr $101+/Nt
Save with Expedia, $18/night less
$125 Crestwood, Illinois Book 3 Nts in Crestwood this Aug Fr $125+/Nt
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$178 Evanston, Illinois Hilton Garden Inn Chicago North Shore/Evanston in Aug: $178 & Up
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$97 Rosemont, Illinois Rosemont Savings! Book at BEST WESTERN at O'Hare Fr $97+/Nt
Expedia
$96 Rosemont, Illinois Save in Rosemont: Book 3 Nts in Aug Fr $96+/Nt
Expedia
$143 Rosemont, Illinois Save Big This Aug! Book 3 Nts in Rosemont Fr $143+/Nt
Expedia
$136 Rosemont, Illinois Sheraton Chicago O'Hare on Sale: Book 3 Nts in Aug Fr $136+/Nt
Expedia
$121 Willowbrook, Illinois Book 3.5-Star Champagne Lodge and Luxury Suites Fr $121+/Nt
Expedia
$99 Oakbrook Terrace, Illinois Book 3-Star Hilton Garden Inn Oakbrook Terrace Fr $99+/Nt
Expedia
$85 Bensenville, Illinois Book 3 Nts in Bensenville this Aug Fr $85+/Nt
Expedia
$102 Glenview, Illinois Book 3.5-Star Wyndham Glenview Suites Fr $102+/Nt
Save with Expedia, $18/night less
$108 Des Plaines, Illinois Des Plaines Savings! Book 3 Nts in Aug Fr $108+/Nt
Expedia
$91 Wood Dale, Illinois Wood Dale Savings! Book 3 Nts in Aug Fr $91+/Nt
Expedia
$119 Downers Grove, Illinois Book 3 Nts in Downers Grove this Aug Fr $119+/Nt
Expedia
$136 Itasca, Illinois Aug deal: Eaglewood & Spa Fr $136+/Nt
Save with Expedia, $34/night less
$85 Itasca, Illinois Aug deal: Hyatt Place Itasca Fr $85+/Nt
Expedia
$133 Tinley Park, Illinois Save in Tinley Park: Book 3 Nts in Aug Fr $133+/Nt
Expedia
$101 Northbrook, Illinois Hilton Northbrook in Aug: $101 & Up
Expedia
$117 Lisle, Illinois Book in Lisle: Save this Aug Fr $117+/Nt
Expedia
$70 Lisle, Illinois Book in Lisle: Save at the Hyatt Lisle in Aug Fr $70+/Nt
Expedia
$89 Lisle, Illinois Small budget: Stay in Lisle this Aug Fr $89+/Nt
Expedia
$119 Arlington Heights, Illinois Arlington Heights Savings! Book 3 Nts in Aug Fr $119+/Nt
Expedia
$94 Arlington Heights, Illinois Aug deal: Jameson Suites of Arlington Heights Fr $94+/Nt
Expedia
$79 Deerfield, Illinois Aug deal: Chicago Marriott Suites Deerfield Fr $79+/Nt
Save with Expedia, $19/night less
$93 Deerfield, Illinois $93 & Up: Hyatt Deerfield 3.5-Star Hotel in Deerfield
Expedia
$110 Bolingbrook, Illinois Bolingbrook Savings! Book at aloft Bolingbrook Fr $110+/Nt
Expedia
$96 Carol Stream, Illinois Aug deal: Hampton Inn Chicago-Carol Stream Fr $96+/Nt
Expedia
$1,124 Rosemont, Illinois Save at 4-Star Hotel: 3 Nts + Air to Rosemont Fr $1,124
Expedia
$782 Lombard, Illinois 4.5-Star Lombard Sale! 3 Nts + Air Fr $782
Expedia
$90 Schaumburg, Illinois Schaumburg Savings! Book 3 Nts in Aug Fr $90+/Nt
Expedia
$110+ Michigan City, Indiana Pottawattamie Park Vacation Rental Deals From $110
Tripping
$110 Schaumburg, Illinois Homewood Suites by Hilton Chicago Schaumburg in Aug: $110 & Up
Expedia
$130+ New Buffalo, Michigan Michiana Vacation Rental Deals From $130
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$85 Schaumburg, Illinois Schaumburg Savings! Book 3 Nts in Aug Fr $85+/Nt
Expedia
$144+ New Buffalo, Michigan Hooks Corner Vacation Rental Deals From $144
Tripping
$104 Schaumburg, Illinois Save in Schaumburg: Book 3 Nts in Aug Fr $104+/Nt
Expedia
$113 Naperville, Illinois Book the Hampton Inn Chicago Naperville 3 Nts in Aug Fr $113+/Nt
Expedia
$80 Naperville, Illinois BEST WESTERN Naperville Inn on Sale: Book 3 Nts in Aug Fr $80+/Nt
Expedia
$104 Lincolnshire, Illinois Book 3 Nts in Lincolnshire this Aug Fr $104+/Nt
Expedia
$139 Lincolnshire, Illinois Book in Lincolnshire: Save this Aug Fr $139+/Nt
Expedia
$100 Warrenville, Illinois Hyatt Place Chicago/Naperville/Warrenville in Aug: $100 & Up
Expedia
$94 Warrenville, Illinois Book 3-Star HYATT house Chicago/Naperville/Warrenville Fr $94+/Nt
Expedia
$104 Warrenville, Illinois Small budget: Stay in Warrenville this Aug Fr $104+/Nt
Expedia
$87 Hoffman Estates, Illinois Aug deal: Hampton Inn & Suites Hoffman Estates Fr $87+/Nt
Expedia
$102 Hoffman Estates, Illinois Book 3-Star Hilton Garden Inn Hoffman Estates Fr $102+/Nt
Expedia
$102 Merrillville, Indiana Hampton Inn Merrillville on Sale: Book 3 Nts in Aug Fr $102+/Nt
Expedia
$111 Merrillville, Indiana Save Big This Aug! Book 3 Nts in Merrillville Fr $111+/Nt
Expedia
$107 Lake Forest, Illinois Small budget: Stay in Lake Forest this Aug Fr $107+/Nt
Expedia
$97 Portage, Indiana Small budget: Stay in Portage this Aug Fr $97+/Nt
Expedia
$106 Deer Park, Illinois Aug deal: Hampton Inn and Suites Chicago Deer Park Fr $106+/Nt
Expedia
$116 Joliet, Illinois Book in Joliet: Save this Aug Fr $116+/Nt
Expedia
$111 Mundelein, Illinois DoubleTree by Hilton Libertyville - Mundelein in Aug: $111 & Up
Expedia
$102 Libertyville, Illinois Save in Libertyville: Book 3 Nts in Aug Fr $102+/Nt
Expedia
$113 Saint Charles, Illinois Pheasant Run and Convention Center in Aug: $113 & Up
Expedia
$102 Chesterton, Indiana Book in Chesterton: Save this Aug Fr $102+/Nt
Expedia
$126 Aurora, Illinois Aurora Savings! Book 3 Nts in Aug Fr $126+/Nt
Expedia
$146 Gurnee, Illinois Save Big This Aug! Book 3 Nts in Gurnee Fr $146+/Nt
Expedia
$138 Valparaiso, Indiana $138 & Up: Inn at Aberdeen 3-Star Hotel in Valparaiso
Save with Expedia, $15/night less
$111 Zion, Illinois Aug deal: Illinois Beach and Conference Center Fr $111+/Nt
Expedia
$114 McHenry, Illinois Save in McHenry: Book 3 Nts in Aug Fr $114+/Nt
Expedia
$149 Oak Lawn, Illinois Save Big This Aug! Book 3 Nts in Oak Lawn Fr $149+/Nt
Expedia
$67 Schiller Park, Illinois Save in Schiller Park: Book 3 Nts in Aug Fr $67+/Nt
Save with Expedia, $45/night less
PRICEDESTINATIONDEAL
$81 Philadelphia, Pennsylvania Cheap Flights from Dallas
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$117 Philadelphia, Pennsylvania Cheap Flights from Boston
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$206 Philadelphia, Pennsylvania Cheap Flights from Denver
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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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