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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$272 Chicago, Illinois Book in Chicago: Save this Dec Fr $272+/Nt
Save with Expedia, $90/night less
$200 Chicago, Illinois Virgin America Current Lowest Fares
DealBase.com
$109 Chicago, Illinois Dec deal: Chicago Marriott Downtown Magnificent Mile Fr $109+/Nt
Expedia
$31 Chicago, Illinois Chicago Vacation Rental Deals From $31
Tripping
$63 Chicago, Illinois Book in Chicago: Save this Dec Fr $63+/Nt
Expedia
$112+ Chicago, Illinois 4.5 Star Luxury Chicago Hotel on Sale! Starting from $112/nt
Jetsetter
$69 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $69+/Nt
Expedia
$125+ Chicago, Illinois Chicago on Sale! Starting From $125/nt
Jetsetter
$76 Chicago, Illinois Book 3-Star Hampton Inn & Suites Chicago - Downtown Fr $76+/Nt
Expedia
$170+ Chicago, Illinois $170: Warwick Allerton Hotel Chicago
Hotels.com
$123 Chicago, Illinois Save at 3-Star Holiday Inn Chicago O'Hare: $123 & Up in Dec
Expedia
$103+ Chicago, Illinois $103: Millennium Knickerbocker, Chicago
Hotels.com
$106 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $106+/Nt
Expedia
$129+ Chicago, Illinois $129: Raffaello Hotel, Chicago
Hotels.com
$99 Chicago, Illinois Special deal: 4-Star Sheraton Chicago and Towers Fr $99+/Nt
Expedia
$212+ Chicago, Illinois $212: Fairmont Chicago at Millennium Park
Hotels.com
$264 Chicago, Illinois Save at 5-Star The Peninsula Chicago: $264 & Up in Dec
Save with Expedia, $131/night less
$188+ Chicago, Illinois $188: The James Chicago
Hotels.com
$119 Chicago, Illinois Save in Chicago: Book 3 Nts in Dec Fr $119+/Nt
Expedia
$157+ Chicago, Illinois $157: The Buckingham Athletic Club & Hotel, Chicago
Priceline.com
$87 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec at The Whitehall Fr $87+/Nt
Save with Expedia, $16/night less
$175+ Chicago, Illinois $175: PUBLIC Chicago
Priceline.com
$292 Chicago, Illinois Dec deal: The Ritz-Carlton Chicago (A Four Seasons ) Fr $292+/Nt
Save with Expedia, $73/night less
$132+ Chicago, Illinois $132: SpringHill Suites Chicago O'Hare by Marriott
Priceline.com
$90 Chicago, Illinois Chicago Savings! Book at Blake Chicago Fr $90+/Nt
Expedia
$135+ Chicago, Illinois $135: Conrad Chicago
Priceline.com
$79 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $79+/Nt
Expedia
$122+ Chicago, Illinois $122: The Willows Hotel, Chicago
Priceline.com
$115 Chicago, Illinois Book the theWit - A DoubleTree by Hilton 3 Nts in Dec Fr $115+/Nt
Expedia
$126+ Chicago, Illinois $126: Kinzie Hotel, Chicago
Priceline.com
$99 Chicago, Illinois Chicago Savings! Book at Allegro Chicago - a Kimpton Fr $99+/Nt
Save with Expedia, $10/night less
$189+ Chicago, Illinois $189: Springhill Suites Chicago Downtown/ River North
Priceline.com
$126 Chicago, Illinois Book the Palomar Chicago, a Kimpton 3 Nts in Dec Fr $126+/Nt
Save with Expedia, $13/night less
$155+ Chicago, Illinois $155: Sofitel Chicago Water Tower
Priceline.com
$68 Chicago, Illinois Save in Chicago: Book 3 Nts in Dec Fr $68+/Nt
Save with Expedia, $11/night less
$158+ Chicago, Illinois $158: dana hotel and spa, Chicago
Priceline.com
$126 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $126+/Nt
Save with Expedia, $13/night less
$125+ Chicago, Illinois $125: Embassy Suites Chicago Downtown
Priceline.com
$91 Chicago, Illinois Dec deal: Courtyard Chicago Downtown/Magnificent Mile Fr $91+/Nt
Expedia
$169+ Chicago, Illinois $169: The Westin Chicago River North
Priceline.com
$136 Chicago, Illinois Special deal: 4-Star Fairmont Chicago Millennium Park Fr $136+/Nt
Save with Expedia, $23/night less
$79 Chicago, Illinois Save Big This Dec! Book 3 Nts in Chicago Fr $79+/Nt
Expedia
$69 Chicago, Illinois Book the Travelodge Chicago Downtown 3 Nts in Dec Fr $69+/Nt
Expedia
$108 Chicago, Illinois PUBLIC Chicago on Sale: Book 3 Nts in Dec Fr $108+/Nt
Expedia
$68 Chicago, Illinois Chicago Savings! Book 3 Nts in Dec Fr $68+/Nt
Expedia
$80 Chicago, Illinois Book in Chicago: Save this Dec Fr $80+/Nt
Save with Expedia, $19/night less
$79 Chicago, Illinois Small budget: Stay in Chicago this Dec Fr $79+/Nt
Expedia
$90 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $90+/Nt
Save with Expedia, $9/night less
$872 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $872
Expedia
$511 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $511
Expedia
$649 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $649
Expedia
$998 Chicago, Illinois 3.5-Star Chicago Sale! 3 Nts + Air Fr $998
Expedia
$464 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $464
Expedia
$691 Chicago, Illinois Chicago 3.5-Star Hotel Sale! 3 Nts + Air Fr $691
Expedia
$1,375 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $1,375
Expedia
$126 Oak Lawn, Illinois Save Big This Dec! Book 3 Nts in Oak Lawn Fr $126+/Nt
Expedia
$95 Evanston, Illinois The Homestead
Groupon Inc
$84 Burbank, Illinois Dec deal: BEST WESTERN Inn & Suites - Midway Airport Fr $84+/Nt
Save with Expedia, $10/night less
$62 Bridgeview, Illinois Bridgeview Savings! Book 3 Nts in Dec Fr $62+/Nt
Expedia
$74 Countryside, Illinois Book 3 Nts in Countryside this Dec Fr $74+/Nt
Save with Expedia, $19/night less
$57 Schiller Park, Illinois Small budget: Stay in Schiller Park this Dec Fr $57+/Nt
Save with Expedia, $38/night less
$91 Schiller Park, Illinois Schiller Park Savings! Book 3 Nts in Dec Fr $91+/Nt
Expedia
$88 Skokie, Illinois Dec deal: DoubleTree by Hilton Chicago North Shore Fr $88+/Nt
Expedia
$94 Crestwood, Illinois Crestwood Savings! Book 3 Nts in Dec Fr $94+/Nt
Expedia
$123 Evanston, Illinois Save in Evanston: Book 3 Nts in Dec Fr $123+/Nt
Expedia
$103 Rosemont, Illinois Rosemont Savings! Book at Sheraton Chicago O'Hare Fr $103+/Nt
Expedia
$114 Rosemont, Illinois Book 3 Nts in Rosemont this Dec Fr $114+/Nt
Expedia
$139 Oak Brook, Illinois Save Big This Dec! Book 3 Nts in Oak Brook Fr $139+/Nt
Expedia
$75 Oak Brook, Illinois Book 3.5-Star Doubletree Chicago Oak Brook Fr $75+/Nt
Save with Expedia, $24/night less
$114 Willowbrook, Illinois Save Big This Dec! Book 3 Nts in Willowbrook Fr $114+/Nt
Save with Expedia, $31/night less
$99 Oakbrook Terrace, Illinois Small budget: Stay in Oakbrook Terrace this Dec Fr $99+/Nt
Expedia
$90 Des Plaines, Illinois Book in Des Plaines: Save this Dec Fr $90+/Nt
Expedia
$88 Lombard, Illinois Hyatt Place Chicago/Lombard on Sale: Book 3 Nts in Dec Fr $88+/Nt
Save with Expedia, $21/night less
$82 Wood Dale, Illinois Small budget: Stay in Wood Dale this Dec Fr $82+/Nt
Expedia
$89 Downers Grove, Illinois Book in Downers Grove: Save this Dec Fr $89+/Nt
Expedia
$114 Orland Park, Illinois Special deal: 3-Star Homewood Suites Orland Park Fr $114+/Nt
Expedia
$102 Itasca, Illinois Dec deal: Eaglewood & Spa Chicago Fr $102+/Nt
Save with Expedia, $17/night less
$64 Itasca, Illinois Book 3-Star Hyatt Place Itasca Fr $64+/Nt
Save with Expedia, $15/night less
$101 Northbrook, Illinois Save Big This Dec! Book 3 Nts in Northbrook Fr $101+/Nt
Expedia
$99 Lisle, Illinois $99 & Up: Hilton Lisle / Naperville 3.5-Star Hotel in Lisle
Expedia
$99 Bloomingdale, Illinois Book 3 Nts in Bloomingdale this Dec Fr $99+/Nt
Expedia
$96 Arlington Heights, Illinois Book in Arlington Heights: Save this Dec Fr $96+/Nt
Expedia
$54 Arlington Heights, Illinois Book 3 Nts in Arlington Heights this Dec Fr $54+/Nt
Save with Expedia, $18/night less
$102 Matteson, Illinois Matteson Savings! Book 3 Nts in Dec Fr $102+/Nt
Expedia
$79 Deerfield, Illinois Save Big This Dec! Book 3 Nts in Deerfield Fr $79+/Nt
Expedia
$1,615 Lombard, Illinois Save at 4-Star Hotel: 3 Nts + Air to Lombard Fr $1,615
Expedia
$79 Schaumburg, Illinois Book the HYATT house Chicago/Schaumburg 3 Nts in Dec Fr $79+/Nt
Expedia
$130 Union Pier, Michigan Union Pier Vacation Rental Deals From $130
Tripping
$81 Schaumburg, Illinois Dec deal: Homewood Suites by Hilton Chicago Schaumburg Fr $81+/Nt
Expedia
$160 New Buffalo, Michigan New Buffalo Vacation Rental Deals From $160
Tripping
$102 Schaumburg, Illinois Book 3-Star DoubleTree by Hilton Chicago - Schaumburg Fr $102+/Nt
Expedia
$85 Schaumburg, Illinois Book 3.5-Star Hyatt Regency Schaumburg, Chicago Fr $85+/Nt
Expedia
$63 Schaumburg, Illinois Special deal: 3-Star Hilton Garden Inn Schaumburg Fr $63+/Nt
Expedia
$109 Schaumburg, Illinois Schaumburg Savings! Book at Quality Inn Schaumburg Fr $109+/Nt
Expedia
$70 Buffalo Grove, Illinois Dec deal: Wyndham Garden Inn Buffalo Grove Fr $70+/Nt
Save with Expedia, $29/night less
$56 Naperville, Illinois Save Big This Dec! Book 3 Nts at Travelodge Naperville Fr $56+/Nt
Expedia
$68 Naperville, Illinois Save in Naperville: Book 3 Nts in Dec Fr $68+/Nt
Expedia
$68 Lincolnshire, Illinois Dec deal: Hampton Inn and Suites Chicago Lincolnshire Fr $68+/Nt
Save with Expedia, $17/night less
$88 Warrenville, Illinois Book 3 Nts in Warrenville this Dec Fr $88+/Nt
Expedia
$81 Warrenville, Illinois Dec deal: Hilton Garden Inn Naperville/Warrenville Fr $81+/Nt
Expedia
PRICEDESTINATIONDEAL
$117 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$200 New York City, New York Virgin America Current Lowest Fares
DealBase.com
$144 New York City, New York JetBlue Baby, It's Cool Onboard Sale
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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