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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$94 Chicago, Illinois Book in Chicago: Save this Oct Fr $94+/Nt
Expedia
$203 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $203+/Nt
Expedia
$126 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $126+/Nt
Expedia
$119 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $119+/Nt
Save with Expedia, $20/night less
$198 Chicago, Illinois Book in Chicago: Save this Oct Fr $198+/Nt
Expedia
$209 Chicago, Illinois Chicago Savings! Book at Conrad Chicago Fr $209+/Nt
Expedia
$84 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at River Fr $84+/Nt
Save with Expedia, $9/night less
$127 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $127+/Nt
Expedia
$116 Chicago, Illinois Oct deal: Chicago Marriott at Medical District/UIC Fr $116+/Nt
Expedia
$328 Chicago, Illinois Book 5-Star Waldorf Astoria Chicago Fr $328+/Nt
Expedia
$370 Chicago, Illinois The Peninsula Chicago on Sale: Book 3 Nts in Oct Fr $370+/Nt
Save with Expedia, $185/night less
$115 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $115+/Nt
Expedia
$844 Chicago, Illinois Save at 4-Star Hotel: 3 Nts + Air to Chicago Fr $844
Expedia
$121 Chicago, Illinois Book 4-Star The Westin Michigan Avenue Chicago Fr $121+/Nt
Expedia
$96 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $96+/Nt
Expedia
$124 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $124+/Nt
Expedia
$133 Chicago, Illinois Book in Chicago: Save this Oct Fr $133+/Nt
Save with Expedia, $6/night less
$129 Chicago, Illinois Chicago Savings! Book at JW Marriott Chicago Fr $129+/Nt
Expedia
$159 Chicago, Illinois Book 3.5-Star Hilton Suites Chicago/Magnificent Mile Fr $159+/Nt
Expedia
$149 Chicago, Illinois Oct deal: Hyatt Chicago Magnificent Mile Fr $149+/Nt
Expedia
$166 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $166+/Nt
Expedia
$168 Chicago, Illinois Book 4-Star Swissotel Chicago Fr $168+/Nt
Save with Expedia, $42/night less
$135 Chicago, Illinois Chicago Savings! Book at Holiday Inn Chicago O'Hare Fr $135+/Nt
Expedia
$103 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $103+/Nt
Expedia
$336 Chicago, Illinois The Ritz-Carlton Chicago (A Four Seasons ) in Oct: $336 & Up
Save with Expedia, $60/night less
$139 Chicago, Illinois Hilton Chicago O'Hare Airport in Oct: $139 & Up
Expedia
$127 Chicago, Illinois Oct deal: Burnham - a Kimpton Fr $127+/Nt
Save with Expedia, $22/night less
$69 Chicago, Illinois Book in Chicago: Save this Oct Fr $69+/Nt
Expedia
$159 Chicago, Illinois Chicago Savings! Book at Renaissance Chicago Fr $159+/Nt
Expedia
$99 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $99+/Nt
Save with Expedia, $25/night less
$111 Chicago, Illinois Oct deal: Holiday Inn Chicago Downtown Fr $111+/Nt
Expedia
$82 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $82+/Nt
Save with Expedia, $20/night less
$136 Chicago, Illinois Chicago Marriott Downtown Magnificent Mile in Oct: $136 & Up
Expedia
$161 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $161+/Nt
Expedia
$99 Skokie, Illinois Book 3.5-Star DoubleTree by Hilton Chicago North Shore Fr $99+/Nt
Expedia
$554 Rosemont, Illinois Save at 4-Star Hotel: 3 Nts + Air to Rosemont Fr $554
Expedia
$79 Oakbrook Terrace, Illinois Oct deal: Hilton Garden Inn Oakbrook Terrace Fr $79+/Nt
Expedia
$93 Westchester, Illinois Small budget: Stay in Westchester this Oct Fr $93+/Nt
Expedia
$69 Arlington Heights, Illinois Jameson Suites of Arlington Heights in Oct: $69 & Up
Save with Expedia, $23/night less
$234 Lombard, Illinois Save at 4-Star Westin Lombard Yorktown Center: $234 & Up in Oct
Expedia
$135 Evanston, Illinois Book 3-Star Hilton Garden Inn Evanston Fr $135+/Nt
Expedia
$82 Lisle, Illinois Book 3.5-Star Hyatt Lisle in Lisle Fr $82+/Nt
Save with Expedia, $27/night less
$90 Tinley Park, Illinois Oct deal: Hampton Inn Chicago / Tinley Park Fr $90+/Nt
Expedia
$109 Tinley Park, Illinois Small budget: Stay in Tinley Park this Oct Fr $109+/Nt
Expedia
$149 Oak Brook, Illinois Oct deal: The Hyatt Lodge at McDonald's Campus Fr $149+/Nt
Expedia
$91 Rosemont, Illinois $91 & Up: BEST WESTERN at O'Hare 3-Star Hotel in Rosemont
Save with Expedia, $16/night less
$117 Lisle, Illinois Hilton Lisle / Naperville in Oct: $117 & Up
Expedia
$128 Bedford Park, Illinois Hampton Inn Chicago-Midway Airport in Oct: $128 & Up
Expedia
$126 Itasca, Illinois Special deal: 3.5-Star Eaglewood & Spa Chicago Fr $126+/Nt
Expedia
$118 Bolingbrook, Illinois Book 3-Star aloft Bolingbrook Fr $118+/Nt
Expedia
$108 Addison, Illinois Addison Savings! Book at Hampton Inn & Suites Addison Fr $108+/Nt
Expedia
$110 Addison, Illinois Book in Addison: Save this Oct Fr $110+/Nt
Expedia
$68 Schiller Park, Illinois Hampton Inn Chicago-O'Hare International Airport in Oct: $68 & Up
Save with Expedia, $17/night less
$85 Carol Stream, Illinois Book the Hampton Inn Chicago-Carol Stream 3 Nts in Oct Fr $85+/Nt
Expedia
$133 Evanston, Illinois Evanston Savings! Book at Hilton Orrington/Evanston Fr $133+/Nt
Expedia
$109 Downers Grove, Illinois Book in Downers Grove: Save this Oct Fr $109+/Nt
Expedia
$95 Rosemont, Illinois Oct deal: Doubletree Chicago O'Hare Airport - Rosemont Fr $95+/Nt
Expedia
$114 Willowbrook, Illinois Book 3.5-Star Champagne Lodge and Luxury Suites Fr $114+/Nt
Save with Expedia, $31/night less
$89 Rosemont, Illinois Book 3.5-Star Hilton Rosemont / Chicago O'Hare Fr $89+/Nt
Expedia
$93 Rosemont, Illinois Rosemont Savings! Book at Sheraton Chicago O'Hare Fr $93+/Nt
Expedia
$88 Deerfield, Illinois Book 3.5-Star Hyatt Deerfield in Deerfield Fr $88+/Nt
Save with Expedia, $21/night less
$96 Deerfield, Illinois Oct deal: Chicago Marriott Suites Deerfield Fr $96+/Nt
Save with Expedia, $23/night less
$66 Schiller Park, Illinois Small budget: Stay in Schiller Park this Oct Fr $66+/Nt
Save with Expedia, $43/night less
$86 Des Plaines, Illinois Oct deal: Hilton Garden Inn Chicago O'Hare Airport Fr $86+/Nt
Expedia
$145 Bedford Park, Illinois Oct deal: Hilton Garden Inn Chicago Midway Airport Fr $145+/Nt
Expedia
$117 Orland Park, Illinois Homewood Suites Orland Park in Oct: $117 & Up
Expedia
$289 Rosemont, Illinois Small budget: Stay in Rosemont this Oct Fr $289+/Nt
Expedia
$128 Oak Brook, Illinois Save at 3.5-Star Doubletree Chicago Oak Brook: $128 & Up in Oct
Expedia
$73 Bensenville, Illinois Country Inn & Suites O'Hare South in Oct: $73 & Up
Expedia
$78 Glenview, Illinois Save Big This Oct! Book 3 Nts in Glenview Fr $78+/Nt
Save with Expedia, $12/night less
$52 Saint Charles, Illinois Small budget: Stay in Saint Charles this Oct Fr $52+/Nt
Save with Expedia, $17/night less
$72 Schaumburg, Illinois Book 3-Star DoubleTree by Hilton Chicago - Schaumburg Fr $72+/Nt
Expedia
$102 Libertyville, Illinois Oct deal: Hampton Inn and Suites Chicago-Libertyville Fr $102+/Nt
Expedia
$69 Naperville, Illinois Hampton Inn Chicago Naperville in Oct: $69 & Up
Expedia
$121 Hoffman Estates, Illinois Book in Hoffman Estates: Save this Oct Fr $121+/Nt
Expedia
$76 Warrenville, Illinois Save in Warrenville: Book 3 Nts in Oct Fr $76+/Nt
Expedia
$79 Gurnee, Illinois Gurnee Savings! Book at Hampton Inn Chicago/Gurnee Fr $79+/Nt
Expedia
$115 Zion, Illinois Book 3-Star Illinois Beach and Conference Center Fr $115+/Nt
Expedia
$102 Valparaiso, Indiana Save Big This Oct! Book 3 Nts in Valparaiso Fr $102+/Nt
Expedia
$95 Merrillville, Indiana Book in Merrillville: Save this Oct Fr $95+/Nt
Expedia
$93 Saint Charles, Illinois Save Big This Oct! Book 3 Nts in Saint Charles Fr $93+/Nt
Expedia
$93 Mundelein, Illinois DoubleTree by Hilton Libertyville - Mundelein in Oct: $93 & Up
Expedia
$72 Warrenville, Illinois Oct deal: Hyatt Place Chicago/Naperville/Warrenville Fr $72+/Nt
Save with Expedia, $17/night less
$88 Warrenville, Illinois Book 3-Star HYATT house Chicago/Naperville/Warrenville Fr $88+/Nt
Save with Expedia, $21/night less
$93 Hoffman Estates, Illinois Oct deal: Hilton Garden Inn Hoffman Estates Fr $93+/Nt
Expedia
$78 Naperville, Illinois Save in Naperville: Book 3 Nts in Oct Fr $78+/Nt
Save with Expedia, $14/night less
$71 Schaumburg, Illinois Book the Hilton Garden Inn Schaumburg 3 Nts in Oct Fr $71+/Nt
Expedia
$104 Lake Forest, Illinois Book 3-Star Hilton Garden Inn Lake Forest Mettawa Fr $104+/Nt
Expedia
$173 Naperville, Illinois Small budget: Stay in Naperville this Oct Fr $173+/Nt
Expedia
$85 Schaumburg, Illinois Book 3.5-Star Hyatt Regency Schaumburg, Chicago Fr $85+/Nt
Expedia
$98 Lombard, Illinois $98 & Up: Hyatt Place Chicago/Lombard 3-Star Hotel in Lombard
Expedia
$89 Schaumburg, Illinois Comfort Suites Schaumburg
Groupon Inc
$74 Gurnee, Illinois Small budget: Stay in Gurnee this Oct Fr $74+/Nt
Save with Expedia, $12/night less
$102 Aurora, Illinois Small budget: Stay in Aurora this Oct Fr $102+/Nt
Expedia
$88 Hoffman Estates, Illinois Book 3-Star Hyatt Place Hoffman Estates Fr $88+/Nt
Save with Expedia, $21/night less
$51 Bridgeview, Illinois Small budget: Stay in Bridgeview this Oct Fr $51+/Nt
Save with Expedia, $12/night less
$72 Collinsville, Illinois Save Big This Oct! Book 3 Nts in Collinsville Fr $72+/Nt
Expedia
$109 Bloomington, Illinois Save in Bloomington: Book 3 Nts in Oct Fr $109+/Nt
Expedia
$99 Deer Park, Illinois Oct deal: Hampton Inn and Suites Chicago Deer Park Fr $99+/Nt
Expedia
$149 Bloomingdale, Illinois Small budget: Stay in Bloomingdale this Oct Fr $149+/Nt
Expedia
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$260 New York City, New York American Airlines Domestic Getaways for This Weekend - 10/24/14
DealBase.com
$212 New York City, New York Cheap Flights from Raleigh
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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