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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$170 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $170+/Nt
Expedia
$169 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $169+/Nt
Expedia
$246 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $246+/Nt
Expedia
$745 Chicago, Illinois Chicago 4-Star Hotel Sale! 3 Nts + Air Fr $745
Expedia
$186 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $186+/Nt
Expedia
$224 Chicago, Illinois Residence Inn Chicago Downtown / River North in Oct: $224 & Up
Expedia
$760 Chicago, Illinois 4-Star Chicago Sale! 3 Nts + Air Fr $760
Expedia
$110 Chicago, Illinois BEST WESTERN Grant Park in Oct: $110 & Up
Save with Expedia, $27/night less
$152 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $152+/Nt
Save with Expedia, $37/night less
$159 Chicago, Illinois Chicago Savings! Book at ACME Company Chicago Fr $159+/Nt
Save with Expedia, $17/night less
$186 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $186+/Nt
Expedia
$159 Chicago, Illinois Save at 3.5-Star Hyatt Regency McCormick Place: $159 & Up in Oct
Expedia
$179 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $179+/Nt
Expedia
$199 Chicago, Illinois Book the Comfort Suites Michigan Avenue 3 Nts in Oct Fr $199+/Nt
Expedia
$193 Chicago, Illinois Chicago Savings! Book at InterContinental Chicago Fr $193+/Nt
Expedia
$249 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Oct: $249 & Up
Expedia
$276 Chicago, Illinois The Blackstone A Renaissance in Oct: $276 & Up
Expedia
$139 Chicago, Illinois Book in Chicago: Save this Oct Fr $139+/Nt
Expedia
$239 Chicago, Illinois Book in Chicago: Save at the The Drake in Oct Fr $239+/Nt
Expedia
$236 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $236+/Nt
Expedia
$138 Chicago, Illinois Chicago Savings! Book at Congress Plaza Fr $138+/Nt
Expedia
$194 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $194+/Nt
Expedia
$259 Chicago, Illinois Oct deal: Hyatt Chicago Magnificent Mile Fr $259+/Nt
Expedia
$203 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $203+/Nt
Expedia
$115 Chicago, Illinois Book 3.5-Star Club Quarters Chicago - Central Loop Fr $115+/Nt
Save with Expedia, $8/night less
$97 Rosemont, Illinois Rosemont Savings! Book at BEST WESTERN at O'Hare Fr $97+/Nt
Save with Expedia, $17/night less
$731 Rosemont, Illinois Save at 4-Star Hotel: 3 Nts + Air to Rosemont Fr $731
Expedia
$488 Lombard, Illinois Lombard 4-Star Hotel Sale! 3 Nts + Air Fr $488
Expedia
$89 Oakbrook Terrace, Illinois Book 3-Star Hilton Garden Inn Oakbrook Terrace Fr $89+/Nt
Expedia
$129 Bloomingdale, Illinois Special deal: 3.5-Star Hilton Chicago/Indian Lakes Fr $129+/Nt
Expedia
$126 Rosemont, Illinois Save at 3.5-Star Sheraton Chicago O'Hare: $126 & Up in Oct
Expedia
$97 Tinley Park, Illinois Hampton Inn Chicago / Tinley Park in Oct: $97 & Up
Expedia
$126 Rosemont, Illinois Book 3.5-Star Hilton Rosemont / Chicago O'Hare Fr $126+/Nt
Expedia
$117 Tinley Park, Illinois Oct deal: Hilton Garden Inn Chicago/Tinley Park Fr $117+/Nt
Expedia
$178 Rosemont, Illinois The Westin O'Hare on Sale: Book 3 Nts in Oct Fr $178+/Nt
Expedia
$114 Schiller Park, Illinois Save in Schiller Park: Book 3 Nts in Oct Fr $114+/Nt
Save with Expedia, $6/night less
$145 Bedford Park, Illinois Book 3-Star Hilton Garden Inn Chicago Midway Airport Fr $145+/Nt
Expedia
$169 Evanston, Illinois Save in Evanston: Book 3 Nts in Oct Fr $169+/Nt
Expedia
$96 Rosemont, Illinois Book in Rosemont: Save this Oct Fr $96+/Nt
Save with Expedia, $23/night less
$122 Skokie, Illinois Oct deal: Holiday Inn Chicago North Shore (Skokie) Fr $122+/Nt
Expedia
$153 Lisle, Illinois Lisle Savings! Book at Hilton Lisle / Naperville Fr $153+/Nt
Expedia
$108 Des Plaines, Illinois Book 3-Star Hilton Garden Inn Chicago O'Hare Airport Fr $108+/Nt
Expedia
$73 Wood Dale, Illinois Save in Wood Dale: Book 3 Nts in Oct Fr $73+/Nt
Expedia
$174 Evanston, Illinois Book 3 Nts in Evanston this Oct Fr $174+/Nt
Expedia
$136 Bedford Park, Illinois Book 3 Nts in Bedford Park this Oct Fr $136+/Nt
Expedia
$144 Oak Lawn, Illinois Special deal: 3.5-Star Hilton Chicago/Oak Lawn Fr $144+/Nt
Expedia
$109 Downers Grove, Illinois Small budget: Stay in Downers Grove this Oct Fr $109+/Nt
Expedia
$54 Bridgeview, Illinois Book the Super 8 Bridgeview/Chicago Area 3 Nts in Oct Fr $54+/Nt
Expedia
$96 Crestwood, Illinois Book 3 Nts in Crestwood this Oct Fr $96+/Nt
Expedia
$80 Countryside, Illinois Oct deal: BEST WESTERN Chicagoland - Countryside Fr $80+/Nt
Save with Expedia, $11/night less
$83 Burbank, Illinois Save in Burbank: Book 3 Nts in Oct Fr $83+/Nt
Save with Expedia, $21/night less
$75 Bensenville, Illinois Small budget: Stay in Bensenville this Oct Fr $75+/Nt
Expedia
$146 Itasca, Illinois Itasca Savings! Book at Eaglewood & Spa Chicago Fr $146+/Nt
Expedia
$236 Evanston, Illinois Small budget: Stay in Evanston this Oct Fr $236+/Nt
Save with Expedia, $17/night less
$81 Addison, Illinois Book 3 Nts in Addison this Oct Fr $81+/Nt
Expedia
$109 Lombard, Illinois Lombard Savings! Book at Hyatt Place Chicago/Lombard Fr $109+/Nt
Expedia
$99 Rosemont, Illinois Book in Rosemont: Save this Oct Fr $99+/Nt
Expedia
$90 Westchester, Illinois Save in Westchester: Book 3 Nts in Oct Fr $90+/Nt
Expedia
$105 Lisle, Illinois Oct deal: Hyatt Lisle Fr $105+/Nt
Save with Expedia, $34/night less
$102 Matteson, Illinois Hampton Inn & Suites Chicago Southland-Matteson in Oct: $102 & Up
Expedia
$109 Oakbrook Terrace, Illinois Book 3 Nts in Oakbrook Terrace this Oct Fr $109+/Nt
Expedia
$149 Oak Brook, Illinois The Hyatt Lodge at McDonald's Campus in Oct: $149 & Up
Expedia
$80 Arlington Heights, Illinois DoubleTree by Hilton Chicago - Arlington Heights in Oct: $80 & Up
Expedia
$149 Techny, Illinois Sybaris Pool Suites - Northbrook
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$802 Schaumburg, Illinois 3.5-Star Schaumburg Sale! 3 Nts + Air Fr $802
Expedia
$65 Buffalo Grove, Illinois Save Big This Oct! Book 3 Nts in Buffalo Grove Fr $65+/Nt
Save with Expedia, $28/night less
$108 Schaumburg, Illinois Special deal: 3-Star Hilton Garden Inn Schaumburg Fr $108+/Nt
Expedia
$76 Warrenville, Illinois Book 3 Nts in Warrenville this Oct Fr $76+/Nt
Expedia
$125 Bolingbrook, Illinois Bolingbrook Savings! Book at aloft Bolingbrook Fr $125+/Nt
Expedia
$74 Gurnee, Illinois Gurnee Savings! Book at BEST WESTERN Gurnee & Suites Fr $74+/Nt
Save with Expedia, $12/night less
$80 Schaumburg, Illinois Oct deal: DoubleTree by Hilton Chicago - Schaumburg Fr $80+/Nt
Expedia
$111 Merrillville, Indiana Hilton Garden Inn Merrillville in Oct: $111 & Up
Expedia
$123 Lincolnshire, Illinois Save in Lincolnshire: Book 3 Nts in Oct Fr $123+/Nt
Expedia
$110 Schaumburg, Illinois Homewood Suites by Hilton Chicago Schaumburg in Oct: $110 & Up
Expedia
$100 Deer Park, Illinois Book in Deer Park: Save this Oct Fr $100+/Nt
Expedia
$96 Merrillville, Indiana Small budget: Stay in Merrillville this Oct Fr $96+/Nt
Expedia
$85 Elgin, Illinois Save in Elgin: Book 3 Nts in Oct Fr $85+/Nt
Expedia
$106 Valparaiso, Indiana Oct deal: Hampton Inn & Suites Valparaiso Fr $106+/Nt
Expedia
$76 Hoffman Estates, Illinois Book 3 Nts in Hoffman Estates this Oct Fr $76+/Nt
Expedia
$143 Bloomingdale, Illinois Save in Bloomingdale: Book 3 Nts in Oct Fr $143+/Nt
Expedia
$85 Lake Forest, Illinois Book in Lake Forest: Save this Oct Fr $85+/Nt
Expedia
$126 Saint Charles, Illinois Save in Saint Charles: Book 3 Nts in Oct Fr $126+/Nt
Expedia
$102 Lincolnshire, Illinois Book 3-Star Homewood Suites by Hilton Lincolnshire Fr $102+/Nt
Expedia
$80 Hoffman Estates, Illinois Oct deal: Hyatt Place Hoffman Estates Fr $80+/Nt
Save with Expedia, $19/night less
$91 Naperville, Illinois Save Big This Oct! Book 3 Nts in Naperville Fr $91+/Nt
Expedia
$134 Gurnee, Illinois Book in Gurnee: Save this Oct Fr $134+/Nt
Expedia
$212 Rosemont, Illinois Book 4.5-Star InterContinental Chicago O'Hare Fr $212+/Nt
Expedia
$78 Naperville, Illinois Oct deal: BEST WESTERN Naperville Inn Fr $78+/Nt
Save with Expedia, $14/night less
$99 Northbrook, Illinois Oct deal: Hilton Northbrook Fr $99+/Nt
Expedia
$89 Hoffman Estates, Illinois Special deal: 3-Star Hilton Garden Inn Hoffman Estates Fr $89+/Nt
Expedia
$116 McHenry, Illinois Small budget: Book Hampton Inn - McHenry 3 Nts in Oct Fr $116+/Nt
Expedia
$51 O'Fallon, Illinois Save in O'Fallon: Book 3 Nts in Oct Fr $51+/Nt
Expedia
$72 Collinsville, Illinois Collinsville Savings! Book at Hampton Inn Collinsville Fr $72+/Nt
Expedia
$88 Lincoln, Illinois Book in Lincoln: Save this Oct Fr $88+/Nt
Expedia
$117 Champaign, Illinois Save in Champaign: Book 3 Nts in Oct Fr $117+/Nt
Expedia
$96 Fairview Heights, Illinois Save in Fairview Heights: Book 3 Nts in Oct Fr $96+/Nt
Expedia
$98 Collinsville, Illinois Small budget: Stay in Collinsville this Oct Fr $98+/Nt
Expedia
$79 Schaumburg, Illinois Oct deal: HYATT house Chicago/Schaumburg Fr $79+/Nt
Expedia
$153 Bloomingdale, Illinois Residence Inn Chicago Bloomingdale in Oct: $153 & Up
Expedia
$68 Zion, Illinois Illinois Beach and Conference Center in Oct: $68 & Up
Save with Expedia, $36/night less
PRICEDESTINATIONDEAL
$145 New York City, New York Cheap Flights from Washington, DC
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$215 New York City, New York American Airlines US Flight Deals
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$324 New York City, New York Cheap Flights from San Francisco
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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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