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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$684 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $684
Expedia
$1,464 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,464
Expedia
$76 Burbank, Illinois Book 3 Nts in Burbank this Jan Fr $76+/Nt
Save with Expedia, $19/night less
$43+ Downers Grove, Illinois Downers Grove Vacation Rental Deals From $43
Tripping
$126 Bedford Park, Illinois Book 3-Star Hilton Garden Inn Chicago Midway Airport Fr $126+/Nt
Expedia
$126 Oak Lawn, Illinois Book 3 Nts in Oak Lawn this Jan Fr $126+/Nt
Expedia
$62 Bridgeview, Illinois Jan deal: Super 8 Bridgeview/Chicago Area Fr $62+/Nt
Expedia
$69 Countryside, Illinois BEST WESTERN Chicagoland - Countryside in Jan: $69 & Up
Save with Expedia, $17/night less
$85 Schiller Park, Illinois Book in Schiller Park: Save this Jan Fr $85+/Nt
Save with Expedia, $21/night less
$87 Schiller Park, Illinois Small budget: Stay in Schiller Park this Jan Fr $87+/Nt
Expedia
$103 Skokie, Illinois Book 3-Star Holiday Inn Chicago North Shore (Skokie) Fr $103+/Nt
Expedia
$125 Evanston, Illinois Evanston Savings! Book at Hilton Garden Inn Evanston Fr $125+/Nt
Expedia
$104 Rosemont, Illinois Sheraton Chicago O'Hare in Jan: $104 & Up
Expedia
$93 Skokie, Illinois Jan deal: DoubleTree by Hilton Chicago North Shore Fr $93+/Nt
Expedia
$76 Westchester, Illinois Save Big This Jan! Book 3 Nts in Westchester Fr $76+/Nt
Expedia
$99 Rosemont, Illinois Save in Rosemont: Book 3 Nts in Jan Fr $99+/Nt
Expedia
$149 Oak Brook, Illinois Save in Oak Brook: Book 3 Nts in Jan Fr $149+/Nt
Expedia
$139 Oak Brook, Illinois Doubletree Chicago Oak Brook in Jan: $139 & Up
Expedia
$126 Bedford Park, Illinois Jan deal: Hampton Inn Chicago-Midway Airport Fr $126+/Nt
Expedia
$164 Rosemont, Illinois Rosemont Savings! Book at The Westin O'Hare Fr $164+/Nt
Expedia
$85 Des Plaines, Illinois Hilton Garden Inn Chicago O'Hare Airport in Jan: $85 & Up
Expedia
$73 Oakbrook Terrace, Illinois Book 3-Star Hilton Garden Inn Oakbrook Terrace Fr $73+/Nt
Expedia
$99 Downers Grove, Illinois Book 3 Nts in Downers Grove this Jan Fr $99+/Nt
Expedia
$102 Rosemont, Illinois Book 3.5-Star Hyatt Rosemont in Rosemont Fr $102+/Nt
Expedia
$118 Alsip, Illinois Book 3.5-Star Doubletree Chicago / Alsip in Alsip Fr $118+/Nt
Expedia
$102 Wood Dale, Illinois Save Big This Jan! Book 3 Nts in Wood Dale Fr $102+/Nt
Expedia
$105 Rosemont, Illinois Book in Rosemont: Save this Jan Fr $105+/Nt
Expedia
$79 Glenview, Illinois Glenview Savings! Book at Wyndham Glenview Suites Fr $79+/Nt
Save with Expedia, $19/night less
$71 Itasca, Illinois Book in Itasca: Save at the Hyatt Place Itasca in Jan Fr $71+/Nt
Expedia
$57 Schiller Park, Illinois Schiller Park Savings! Book at O'Hare Inn & Suites Fr $57+/Nt
Save with Expedia, $38/night less
$133 Itasca, Illinois Save in Itasca: Book 3 Nts in Jan Fr $133+/Nt
Expedia
$91 Rosemont, Illinois BEST WESTERN at O'Hare in Jan: $91 & Up
Save with Expedia, $16/night less
$103 Orland Park, Illinois Book the Homewood Suites Orland Park 3 Nts in Jan Fr $103+/Nt
Expedia
$116 Rosemont, Illinois Book 3.5-Star Hilton Rosemont / Chicago O'Hare Fr $116+/Nt
Expedia
$99 Tinley Park, Illinois Book 3-Star Hilton Garden Inn Chicago/Tinley Park Fr $99+/Nt
Expedia
$80 Lombard, Illinois Lombard Savings! Book at Hyatt Place Chicago/Lombard Fr $80+/Nt
Expedia
$96 Crestwood, Illinois Crestwood Savings! Book 3 Nts in Jan Fr $96+/Nt
Expedia
$81 Northbrook, Illinois Northbrook Savings! Book at Hilton Northbrook Fr $81+/Nt
Expedia
$87 Addison, Illinois Hampton Inn & Suites Addison in Jan: $87 & Up
Expedia
$136 Evanston, Illinois Book 4-Star Hilton Orrington/Evanston Fr $136+/Nt
Expedia
$96 Lisle, Illinois Book the Sheraton Lisle 3 Nts in Jan Fr $96+/Nt
Expedia
$79 Lisle, Illinois Save Big This Jan! Book 3 Nts at Hyatt Lisle Fr $79+/Nt
Expedia
$93 Oakbrook Terrace, Illinois Save in Oakbrook Terrace: Book 3 Nts in Jan Fr $93+/Nt
Expedia
$75 Willowbrook, Illinois Jan deal: Champagne Lodge and Luxury Suites Fr $75+/Nt
Save with Expedia, $19/night less
$96 Tinley Park, Illinois Hampton Inn Chicago / Tinley Park in Jan: $96 & Up
Expedia
$99 Bloomingdale, Illinois Special deal: 3.5-Star Hilton Chicago/Indian Lakes Fr $99+/Nt
Expedia
$102 Matteson, Illinois Matteson Savings! Book 3 Nts in Jan Fr $102+/Nt
Expedia
$116 Bloomingdale, Illinois Save in Bloomingdale: Book 3 Nts in Jan Fr $116+/Nt
Expedia
$93 Deerfield, Illinois Deerfield Savings! Book 3 Nts in Jan Fr $93+/Nt
Expedia
$54 Arlington Heights, Illinois Jan deal: Jameson Suites of Arlington Heights Fr $54+/Nt
Save with Expedia, $18/night less
$105 Addison, Illinois Addison Savings! Book at Hilton Garden Inn Addison Fr $105+/Nt
Expedia
$85 Arlington Heights, Illinois Save in Arlington Heights: Book 3 Nts in Jan Fr $85+/Nt
Expedia
$87 Bolingbrook, Illinois Bolingbrook Savings! Book at aloft Bolingbrook Fr $87+/Nt
Expedia
$153 Bloomingdale, Illinois Book 3-Star Residence Inn Chicago Bloomingdale Fr $153+/Nt
Expedia
$114 Lisle, Illinois Hilton Lisle / Naperville in Jan: $114 & Up
Expedia
$85 Carol Stream, Illinois Jan deal: Hampton Inn Chicago-Carol Stream Fr $85+/Nt
Expedia
$99 Deerfield, Illinois Chicago Marriott Suites Deerfield in Jan: $99 & Up
Expedia
$564 Lombard, Illinois Save at 4-Star Hotel: 3 Nts + Air to Lombard Fr $564
Expedia
$98 Schaumburg, Illinois Book the HYATT house Chicago/Schaumburg 3 Nts in Jan Fr $98+/Nt
Expedia
$120+ Beverly Shores, Indiana Beverly Shores Vacation Rental Deals From $120
Tripping
$89 Schaumburg, Illinois Jan deal: Hilton Garden Inn Schaumburg Fr $89+/Nt
Expedia
$130+ New Buffalo, Michigan Michiana Vacation Rental Deals From $130
Tripping
$99 Schaumburg, Illinois Small budget: Stay in Schaumburg this Jan Fr $99+/Nt
Expedia
$144+ New Buffalo, Michigan Hooks Corner Vacation Rental Deals From $144
Tripping
$63 Buffalo Grove, Illinois Save at 3-Star Wyndham Garden Inn Buffalo Grove: $63 & Up in Jan
Save with Expedia, $26/night less
$109 Schaumburg, Illinois Small budget: Stay in Schaumburg this Jan Fr $109+/Nt
Expedia
$73 Naperville, Illinois BEST WESTERN Naperville Inn in Jan: $73 & Up
Save with Expedia, $12/night less
$93 Naperville, Illinois Hampton Inn Chicago Naperville in Jan: $93 & Up
Expedia
$85 Schaumburg, Illinois Save Big This Jan! Book 3 Nts in Schaumburg Fr $85+/Nt
Expedia
$111 Warrenville, Illinois HYATT house Chicago/Naperville/Warrenville in Jan: $111 & Up
Expedia
$87 Lincolnshire, Illinois Hampton Inn and Suites Chicago Lincolnshire in Jan: $87 & Up
Save with Expedia, $9/night less
$75 Hoffman Estates, Illinois Hampton Inn & Suites Hoffman Estates in Jan: $75 & Up
Expedia
$98 Warrenville, Illinois Hyatt Place Chicago/Naperville/Warrenville in Jan: $98 & Up
Expedia
$69 Schaumburg, Illinois Book 3-Star DoubleTree by Hilton Chicago - Schaumburg Fr $69+/Nt
Save with Expedia, $10/night less
$93 Warrenville, Illinois Book 3-Star Hilton Garden Inn Naperville/Warrenville Fr $93+/Nt
Expedia
$95 Lincolnshire, Illinois Homewood Suites by Hilton Lincolnshire in Jan: $95 & Up
Expedia
$93 Hoffman Estates, Illinois Save in Hoffman Estates: Book 3 Nts in Jan Fr $93+/Nt
Expedia
$45 Naperville, Illinois Naperville Savings! Book at Travelodge Naperville Fr $45+/Nt
Expedia
$106 Merrillville, Indiana Small budget: Stay in Merrillville this Jan Fr $106+/Nt
Expedia
$99 Lake Forest, Illinois Jan deal: Hilton Garden Inn Lake Forest Mettawa Fr $99+/Nt
Expedia
$171 Naperville, Illinois $171 & Up: Arista at CityGate Centre 4.5-Star Hotel in Naperville
Save with Expedia, $18/night less
$182 Naperville, Illinois Small budget: Stay in Naperville this Jan Fr $182+/Nt
Expedia
$107 Merrillville, Indiana Special deal: 3-Star Hilton Garden Inn Merrillville Fr $107+/Nt
Expedia
$96 Joliet, Illinois Joliet Savings! Book at Hampton Inn Joliet I-55 Fr $96+/Nt
Expedia
$93 Portage, Indiana Portage Savings! Book at Hampton Inn Portage Fr $93+/Nt
Expedia
$100 Deer Park, Illinois Small budget: Stay in Deer Park this Jan Fr $100+/Nt
Expedia
$102 Libertyville, Illinois Book in Libertyville: Save this Jan Fr $102+/Nt
Expedia
$103 Saint Charles, Illinois Book 3-Star Pheasant Run and Convention Center Fr $103+/Nt
Expedia
$93 Mundelein, Illinois DoubleTree by Hilton Libertyville - Mundelein in Jan: $93 & Up
Expedia
$92 Saint Charles, Illinois Book in Saint Charles: Save this Jan Fr $92+/Nt
Expedia
$103 Chesterton, Indiana Small budget: Stay in Chesterton this Jan Fr $103+/Nt
Expedia
$108 Aurora, Illinois Small budget: Stay in Aurora this Jan Fr $108+/Nt
Expedia
$82 Elgin, Illinois Elgin Savings! Book at Hampton Inn Chicago/Elgin Fr $82+/Nt
Expedia
$110 Valparaiso, Indiana Book the Hampton Inn & Suites Valparaiso 3 Nts in Jan Fr $110+/Nt
Expedia
$67 Gurnee, Illinois Gurnee Savings! Book at BEST WESTERN Gurnee & Suites Fr $67+/Nt
Save with Expedia, $11/night less
$86 Gurnee, Illinois Hampton Inn Chicago/Gurnee on Sale: Book 3 Nts in Jan Fr $86+/Nt
Expedia
$104 Zion, Illinois Save in Zion: Book 3 Nts in Jan Fr $104+/Nt
Expedia
$114 McHenry, Illinois Book the Hampton Inn - McHenry 3 Nts in Jan Fr $114+/Nt
Expedia
$35+ Oak Park, Illinois Oak Park Vacation Rental Deals From $35
Tripping
$80 Champaign, Illinois Save in Champaign: Book 3 Nts in Jan Fr $80+/Nt
Expedia
PRICEDESTINATIONDEAL
$117 New York City, New York Cheap Flights from Washington, DC
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$263 New York City, New York Cheap Flights from Salt Lake City
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$251 New York City, New York Cheap Flights from Milwaukee
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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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