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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$1,433 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $1,433
Expedia
$1,906 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,906
Expedia
$4,792 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $4,792
Expedia
$35+ Oak Park, Illinois Oak Park Vacation Rental Deals From $35
Tripping
$88 Burbank, Illinois May deal: BEST WESTERN Inn & Suites - Midway Airport Fr $88+/Nt
Expedia
$59+ Elmhurst, Illinois Elmhurst Vacation Rental Deals From $59
Tripping
$102 Schiller Park, Illinois Book in Schiller Park: Save this May Fr $102+/Nt
Expedia
$43+ Downers Grove, Illinois Downers Grove Vacation Rental Deals From $43
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$139 Skokie, Illinois May deal: DoubleTree by Hilton Chicago North Shore Fr $139+/Nt
Expedia
$50+ Evanston, Illinois Evanston Vacation Rental Deals From $50
Tripping
$170 Bedford Park, Illinois Book 3-Star Hilton Garden Inn Chicago Midway Airport Fr $170+/Nt
Expedia
$148 Oak Brook, Illinois Save Big This May! Book 3 Nts in Oak Brook Fr $148+/Nt
Expedia
$106 Oakbrook Terrace, Illinois May deal: Hilton Garden Inn Oakbrook Terrace Fr $106+/Nt
Expedia
$121 Crestwood, Illinois Save Big This May! Book 3 Nts in Crestwood Fr $121+/Nt
Expedia
$116 Schiller Park, Illinois Book 3 Nts in Schiller Park this May Fr $116+/Nt
Expedia
$136 Rosemont, Illinois Save in Rosemont: Book 3 Nts in May at Hyatt Rosemont Fr $136+/Nt
Expedia
$117 Des Plaines, Illinois May deal: Hilton Garden Inn Chicago O'Hare Airport Fr $117+/Nt
Expedia
$121 Willowbrook, Illinois Small budget: Stay in Willowbrook this May Fr $121+/Nt
Expedia
$110 Wood Dale, Illinois Save Big This May! Book 3 Nts in Wood Dale Fr $110+/Nt
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$96 Countryside, Illinois BEST WESTERN Chicagoland - Countryside in May: $96 & Up
Expedia
$94 Itasca, Illinois Book 3-Star Hyatt Place Itasca Fr $94+/Nt
Expedia
$119 Westchester, Illinois Hampton Inn Chicago/Westchester (Oak Brook) in May: $119 & Up
Expedia
$141 Itasca, Illinois Book 3 Nts in Itasca this May Fr $141+/Nt
Save with Expedia, $15/night less
$103 Glenview, Illinois Special deal: 3.5-Star Wyndham Glenview Suites Fr $103+/Nt
Save with Expedia, $11/night less
$102 Lisle, Illinois Save in Lisle: Book 3 Nts in May Fr $102+/Nt
Expedia
$162 Evanston, Illinois Hilton Garden Inn Chicago North Shore/Evanston in May: $162 & Up
Expedia
$120 Addison, Illinois Book 3-Star Hilton Garden Inn Addison Fr $120+/Nt
Expedia
$119 Northbrook, Illinois Northbrook Savings! Book at Hilton Northbrook Fr $119+/Nt
Expedia
$133 Orland Park, Illinois Save Big This May! Book 3 Nts in Orland Park Fr $133+/Nt
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$102 Tinley Park, Illinois May deal: Hampton Inn Chicago / Tinley Park Fr $102+/Nt
Expedia
$99 Arlington Heights, Illinois Small budget: Stay in Arlington Heights this May Fr $99+/Nt
Expedia
$116 Rosemont, Illinois Book 3.5-Star Sheraton Chicago O'Hare Fr $116+/Nt
Expedia
$149 Oak Brook, Illinois Book 4-Star The Hyatt Lodge at McDonald's Campus Fr $149+/Nt
Expedia
$116 Lisle, Illinois Hyatt Lisle on Sale: Book 3 Nts in May Fr $116+/Nt
Expedia
$139 Oakbrook Terrace, Illinois Oakbrook Terrace Savings! Book 3 Nts in May Fr $139+/Nt
Expedia
$129 Bloomingdale, Illinois Special deal: 3.5-Star Hilton Chicago/Indian Lakes Fr $129+/Nt
Expedia
$119 Downers Grove, Illinois Book 3 Nts in Downers Grove this May Fr $119+/Nt
Expedia
$126 Tinley Park, Illinois Book 3-Star Hilton Garden Inn Chicago/Tinley Park Fr $126+/Nt
Expedia
$96 Carol Stream, Illinois Book the Hampton Inn Chicago-Carol Stream 3 Nts in May Fr $96+/Nt
Expedia
$1,281 Rosemont, Illinois 4-Star Rosemont Sale! 3 Nts + Air Fr $1,281
Expedia
$647 Rosemont, Illinois 3.5-Star Rosemont Sale! 3 Nts + Air Fr $647
Expedia
$541 Rosemont, Illinois Rosemont 4.5-Star Hotel Sale! 3 Nts + Air Fr $541
Expedia
$1,268 Deerfield, Illinois 3.5-Star Deerfield Sale! 3 Nts + Air Fr $1,268
Expedia
$117 Schaumburg, Illinois Homewood Suites by Hilton Chicago Schaumburg in May: $117 & Up
Expedia
$110+ Michigan City, Indiana Pottawattamie Park Vacation Rental Deals From $110
Tripping
$107 Warrenville, Illinois Warrenville Savings! Book 3 Nts in May Fr $107+/Nt
Expedia
$130+ New Buffalo, Michigan Michiana Vacation Rental Deals From $130
Tripping
$136 Lincolnshire, Illinois May deal: Hampton Inn and Suites Chicago Lincolnshire Fr $136+/Nt
Expedia
$144+ New Buffalo, Michigan Hooks Corner Vacation Rental Deals From $144
Tripping
$80 Naperville, Illinois BEST WESTERN Naperville Inn in May: $80 & Up
Expedia
$85 Hoffman Estates, Illinois Hampton Inn & Suites Hoffman Estates in May: $85 & Up
Expedia
$99 Warrenville, Illinois Book 3-Star Hilton Garden Inn Naperville/Warrenville Fr $99+/Nt
Expedia
$86 Buffalo Grove, Illinois Special deal: 3-Star Wyndham Garden Inn Buffalo Grove Fr $86+/Nt
Save with Expedia, $13/night less
$89 Schaumburg, Illinois May deal: DoubleTree by Hilton Chicago - Schaumburg Fr $89+/Nt
Expedia
$119 Merrillville, Indiana Book 3 Nts in Merrillville this May Fr $119+/Nt
Expedia
$107 Lake Forest, Illinois Book 3 Nts in Lake Forest this May Fr $107+/Nt
Expedia
$85 Schaumburg, Illinois Book 3.5-Star Hyatt Regency Schaumburg, Chicago Fr $85+/Nt
Expedia
$168 Naperville, Illinois $168 & Up: Arista at CityGate Centre 4.5-Star Hotel in Naperville
Save with Expedia, $18/night less
$126 Lincolnshire, Illinois Book 3-Star Homewood Suites by Hilton Lincolnshire Fr $126+/Nt
Expedia
$109 Hoffman Estates, Illinois Hyatt Place Chicago/Hoffman Estates in May: $109 & Up
Expedia
$144 Naperville, Illinois May deal: Hampton Inn Chicago Naperville Fr $144+/Nt
Expedia
$103 Warrenville, Illinois Warrenville Savings! Book 3 Nts in May Fr $103+/Nt
Expedia
$102 Libertyville, Illinois Book 3 Nts in Libertyville this May Fr $102+/Nt
Expedia
$108 Saint Charles, Illinois Special deal: 3-Star Hilton Garden Inn St. Charles Fr $108+/Nt
Expedia
$111 Chesterton, Indiana Book in Chesterton: Save this May Fr $111+/Nt
Expedia
$127 Joliet, Illinois Hampton Inn Joliet I-55 on Sale: Book 3 Nts in May Fr $127+/Nt
Expedia
$99 Saint Charles, Illinois Hampton Inn & Suites Chicago-Saint Charles in May: $99 & Up
Expedia
$106 Deer Park, Illinois Hampton Inn and Suites Chicago Deer Park in May: $106 & Up
Expedia
$85 Elgin, Illinois Book in Elgin: Save this May Fr $85+/Nt
Expedia
$146 Gurnee, Illinois Gurnee Savings! Book at Hampton Inn Chicago/Gurnee Fr $146+/Nt
Expedia
$110 Valparaiso, Indiana May deal: Hampton Inn & Suites Valparaiso Fr $110+/Nt
Expedia
$74 Gurnee, Illinois May deal: BEST WESTERN Gurnee & Suites Fr $74+/Nt
Expedia
$171 Valparaiso, Indiana Book in Valparaiso: Save this May Fr $171+/Nt
Expedia
$100 Zion, Illinois Zion Savings! Book 3 Nts in May Fr $100+/Nt
Expedia
$114 McHenry, Illinois McHenry Savings! Book at Hampton Inn - McHenry Fr $114+/Nt
Expedia
$65 Bridgeview, Illinois Book 3 Nts in Bridgeview this May Fr $65+/Nt
Expedia
$147 Alsip, Illinois Doubletree Chicago / Alsip on Sale: Book 3 Nts in May Fr $147+/Nt
Expedia
$67 Schiller Park, Illinois Small budget: Stay in Schiller Park this May Fr $67+/Nt
Save with Expedia, $45/night less
$141 Oak Lawn, Illinois Book the Hilton Chicago/Oak Lawn 3 Nts in May Fr $141+/Nt
Expedia
$136 Bedford Park, Illinois Small budget: Stay in Bedford Park this May Fr $136+/Nt
Expedia
$128 Rosemont, Illinois Book 4-Star Hyatt Regency O'Hare Fr $128+/Nt
Expedia
$114 Rosemont, Illinois Small budget: Stay in Rosemont this May Fr $114+/Nt
Expedia
$149 Evanston, Illinois Evanston Savings! Book at Hilton Orrington/Evanston Fr $149+/Nt
Expedia
$98 Bensenville, Illinois Country Inn & Suites O'Hare South in May: $98 & Up
Expedia
$132 Rosemont, Illinois Rosemont Savings! Book at BEST WESTERN at O'Hare Fr $132+/Nt
Expedia
$133 Rosemont, Illinois Book 3.5-Star Hilton Rosemont / Chicago O'Hare Fr $133+/Nt
Expedia
$125 Des Plaines, Illinois Save Big This May! Book 3 Nts in Des Plaines Fr $125+/Nt
Expedia
$159 Matteson, Illinois Small budget: Stay in Matteson this May Fr $159+/Nt
Expedia
$145 Bolingbrook, Illinois Bolingbrook Savings! Book at aloft Bolingbrook Fr $145+/Nt
Expedia
$98 Lombard, Illinois Save in Lombard: Book 3 Nts in May Fr $98+/Nt
Expedia
$79 Schaumburg, Illinois Small budget: Stay in Schaumburg this May Fr $79+/Nt
Expedia
$126 Schaumburg, Illinois Small budget: Stay in Schaumburg this May Fr $126+/Nt
Expedia
$50 Naperville, Illinois Small budget: Book Motel 6 Naperville 3 Nts in May Fr $50+/Nt
Expedia
$68 Deerfield, Illinois Deerfield Savings! Book at Hyatt Deerfield Fr $68+/Nt
Expedia
$99 Hoffman Estates, Illinois May deal: Hilton Garden Inn Hoffman Estates Fr $99+/Nt
Expedia
$144 Mundelein, Illinois DoubleTree by Hilton Libertyville - Mundelein in May: $144 & Up
Expedia
$126 Aurora, Illinois May deal: Hampton Inn and Suites Chicago / Aurora Fr $126+/Nt
Expedia
$80 Saint Charles, Illinois Small budget: Stay in Saint Charles this May Fr $80+/Nt
Save with Expedia, $6/night less
$95 O'Fallon, Illinois Book 3 Nts in O'Fallon this May Fr $95+/Nt
Expedia
$94 Collinsville, Illinois Collinsville Savings! Book at Hampton Inn Collinsville Fr $94+/Nt
Expedia
PRICEDESTINATIONDEAL
$79 Philadelphia, Pennsylvania Frontier Airlines Travel Deals
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$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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