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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$356 Chicago, Illinois Book in Chicago: Save this Oct Fr $356+/Nt
Save with Expedia, $39/night less
$102 Chicago, Illinois Oct deal: Millennium Knickerbocker Chicago Fr $102+/Nt
Save with Expedia, $17/night less
$161 Chicago, Illinois Monaco Chicago - a Kimpton in Oct: $161 & Up
Save with Expedia, $69/night less
$109 Chicago, Illinois Embassy Suites Chicago Downtown Lakefront in Oct: $109 & Up
Expedia
$204 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $204+/Nt
Expedia
$137 Chicago, Illinois Book 4-Star Chicago Downtown, Autograph Collection Fr $137+/Nt
Save with Expedia, $46/night less
$128 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct at Omni Chicago Fr $128+/Nt
Save with Expedia, $31/night less
$139 Chicago, Illinois Oct deal: Hilton Chicago O'Hare Airport Fr $139+/Nt
Expedia
$127 Chicago, Illinois Special deal: 4-Star Hard Rock Chicago Fr $127+/Nt
Save with Expedia, $22/night less
$104 Tinley Park, Illinois Oct deal: Hilton Garden Inn Chicago/Tinley Park Fr $104+/Nt
Expedia
$99 Skokie, Illinois Small budget: Stay in Skokie this Oct Fr $99+/Nt
Expedia
$80 Deerfield, Illinois Book the Hyatt Deerfield 3 Nts in Oct Fr $80+/Nt
Save with Expedia, $19/night less
$98 Lombard, Illinois Lombard Savings! Book at Hyatt Place Chicago/Lombard Fr $98+/Nt
Expedia
$495 Rosemont, Illinois Save at 4-Star Hotel: 3 Nts + Air to Rosemont Fr $495
Expedia
$694 Lombard, Illinois Save at 4-Star Hotel: 3 Nts + Air to Lombard Fr $694
Expedia
$51 Bridgeview, Illinois Book in Bridgeview: Save this Oct Fr $51+/Nt
Save with Expedia, $12/night less
$126 Itasca, Illinois Oct deal: Eaglewood & Spa Chicago Fr $126+/Nt
Expedia
$66 Arlington Heights, Illinois Small budget: Stay in Arlington Heights this Oct Fr $66+/Nt
Save with Expedia, $22/night less
$75 Wood Dale, Illinois Save in Wood Dale: Book 3 Nts in Oct Fr $75+/Nt
Expedia
$99 Northbrook, Illinois Save Big This Oct! Book 3 Nts in Northbrook Fr $99+/Nt
Expedia
$72 Bensenville, Illinois Save in Bensenville: Book 3 Nts in Oct Fr $72+/Nt
Expedia
$102 Matteson, Illinois Save Big This Oct! Book 3 Nts in Matteson Fr $102+/Nt
Expedia
$89 Lisle, Illinois Book the Sheraton Lisle 3 Nts in Oct Fr $89+/Nt
Expedia
$126 Oak Brook, Illinois Book 3.5-Star Doubletree Chicago Oak Brook Fr $126+/Nt
Expedia
$177 Rosemont, Illinois Book 3 Nts in Rosemont this Oct Fr $177+/Nt
Expedia
$111 Bolingbrook, Illinois Book the aloft Bolingbrook 3 Nts in Oct Fr $111+/Nt
Expedia
$89 Itasca, Illinois Book in Itasca: Save at the Hyatt Place Itasca in Oct Fr $89+/Nt
Expedia
$149 Oak Brook, Illinois Oct deal: The Hyatt Lodge at McDonald's Campus Fr $149+/Nt
Expedia
$76 Westchester, Illinois Book 3 Nts in Westchester this Oct Fr $76+/Nt
Expedia
$110 Addison, Illinois Book the Hilton Garden Inn Addison 3 Nts in Oct Fr $110+/Nt
Expedia
$114 Willowbrook, Illinois Book 3.5-Star Champagne Lodge and Luxury Suites Fr $114+/Nt
Save with Expedia, $31/night less
$82 Deerfield, Illinois Small budget: Stay in Deerfield this Oct Fr $82+/Nt
Save with Expedia, $27/night less
$98 Crestwood, Illinois Oct deal: Holiday Inn Express Crestwood Fr $98+/Nt
Expedia
$145 Bedford Park, Illinois Book in Bedford Park: Save this Oct Fr $145+/Nt
Expedia
$118 Skokie, Illinois Book 3-Star Holiday Inn Chicago North Shore (Skokie) Fr $118+/Nt
Expedia
$88 Des Plaines, Illinois Book in Des Plaines: Save this Oct Fr $88+/Nt
Expedia
$90 Bloomingdale, Illinois Book the Hilton Chicago/Indian Lakes 3 Nts in Oct Fr $90+/Nt
Expedia
$95 Lisle, Illinois Book 3.5-Star Hilton Lisle / Naperville Fr $95+/Nt
Expedia
$114 Orland Park, Illinois Book 3-Star Homewood Suites Orland Park Fr $114+/Nt
Expedia
$128 Bedford Park, Illinois Hampton Inn Chicago-Midway Airport in Oct: $128 & Up
Expedia
$80 Arlington Heights, Illinois DoubleTree by Hilton Chicago - Arlington Heights in Oct: $80 & Up
Expedia
$102 Alsip, Illinois Book 3 Nts in Alsip this Oct Fr $102+/Nt
Expedia
$117 Oak Lawn, Illinois Oak Lawn Savings! Book at Hilton Chicago/Oak Lawn Fr $117+/Nt
Expedia
$126 Evanston, Illinois Hilton Garden Inn Evanston in Oct: $126 & Up
Expedia
$95 Rosemont, Illinois Save Big This Oct! Book 3 Nts in Rosemont Fr $95+/Nt
Expedia
$91 Rosemont, Illinois $91 & Up: BEST WESTERN at O'Hare 3-Star Hotel in Rosemont
Save with Expedia, $16/night less
$75 Lisle, Illinois Save at 3.5-Star Hyatt Lisle: $75 & Up in Oct
Save with Expedia, $24/night less
$146 Bloomingdale, Illinois Book 3 Nts in Bloomingdale this Oct Fr $146+/Nt
Expedia
$92 Schiller Park, Illinois Save in Schiller Park: Book 3 Nts in Oct Fr $92+/Nt
Expedia
$908 Schaumburg, Illinois 3.5-Star Schaumburg Sale! 3 Nts + Air Fr $908
Expedia
$89 Schaumburg, Illinois Comfort Suites Schaumburg
Groupon Inc
$88 Hoffman Estates, Illinois Small budget: Stay in Hoffman Estates this Oct Fr $88+/Nt
Save with Expedia, $21/night less
$93 Hoffman Estates, Illinois Oct deal: Hilton Garden Inn Hoffman Estates Fr $93+/Nt
Expedia
$85 Mundelein, Illinois Book 3 Nts in Mundelein this Oct Fr $85+/Nt
Expedia
$95 Merrillville, Indiana Small budget: Stay in Merrillville this Oct Fr $95+/Nt
Expedia
$101 Lincolnshire, Illinois Oct deal: Homewood Suites by Hilton Lincolnshire Fr $101+/Nt
Expedia
$86 Lake Forest, Illinois Hilton Garden Inn Lake Forest Mettawa in Oct: $86 & Up
Expedia
$76 Warrenville, Illinois Small budget: Stay in Warrenville this Oct Fr $76+/Nt
Expedia
$89 Naperville, Illinois Book the Hampton Inn Chicago Naperville 3 Nts in Oct Fr $89+/Nt
Expedia
$73 Schaumburg, Illinois Book 3-Star Hilton Garden Inn Schaumburg in Schaumburg Fr $73+/Nt
Expedia
$79 Naperville, Illinois Save Big This Oct! Book 3 Nts in Naperville Fr $79+/Nt
Save with Expedia, $13/night less
$76 Hoffman Estates, Illinois Save in Hoffman Estates: Book 3 Nts in Oct Fr $76+/Nt
Expedia
$109 McHenry, Illinois Book in McHenry: Save this Oct Fr $109+/Nt
Expedia
$85 Schaumburg, Illinois Oct deal: Homewood Suites by Hilton Chicago Schaumburg Fr $85+/Nt
Expedia
$173 Naperville, Illinois Naperville Savings! Book 3 Nts in Oct Fr $173+/Nt
Expedia
$61 Lincolnshire, Illinois Book 3 Nts in Lincolnshire this Oct Fr $61+/Nt
Save with Expedia, $20/night less
$49 Saint Charles, Illinois Save in Saint Charles: Book 3 Nts in Oct Fr $49+/Nt
Save with Expedia, $17/night less
$95 Portage, Indiana Portage Savings! Book at Hampton Inn Portage Fr $95+/Nt
Expedia
$111 Zion, Illinois Save in Zion: Book 3 Nts in Oct Fr $111+/Nt
Expedia
$99 Deer Park, Illinois Hampton Inn and Suites Chicago Deer Park in Oct: $99 & Up
Expedia
$74 Gurnee, Illinois Gurnee Savings! Book at BEST WESTERN Gurnee & Suites Fr $74+/Nt
Save with Expedia, $12/night less
$90 Tinley Park, Illinois Save Big This Oct! Book 3 Nts in Tinley Park Fr $90+/Nt
Expedia
$72 Schaumburg, Illinois Book in Schaumburg: Save this Oct Fr $72+/Nt
Expedia
$102 Aurora, Illinois Oct deal: Hampton Inn and Suites Chicago / Aurora Fr $102+/Nt
Expedia
$102 Joliet, Illinois Oct deal: Hampton Inn Joliet I-55 Fr $102+/Nt
Expedia
$746 Normal, Illinois 3.5-Star Normal Sale! 3 Nts + Air Fr $746
Expedia
$99 Downers Grove, Illinois Save Big This Oct! Book 3 Nts in Downers Grove Fr $99+/Nt
Expedia
$79 Oakbrook Terrace, Illinois Book 3 Nts in Oakbrook Terrace this Oct Fr $79+/Nt
Expedia
$80 Champaign, Illinois Oct deal: Country Inn & Suites Champaign-North Fr $80+/Nt
Expedia
$72 Collinsville, Illinois Hampton Inn Collinsville in Oct: $72 & Up
Expedia
$97 Rockford, Illinois Hilton Garden Inn Rockford in Oct: $97 & Up
Expedia
$99 Oakbrook Terrace, Illinois Save Big This Oct! Book 3 Nts in Oakbrook Terrace Fr $99+/Nt
Expedia
$90 Moline, Illinois Save Big This Oct! Book 3 Nts in Moline Fr $90+/Nt
Expedia
$112 Champaign, Illinois Book in Champaign: Save this Oct Fr $112+/Nt
Expedia
$133 Champaign, Illinois Oct deal: Homewood Suites by Hilton Champaign-Urbana Fr $133+/Nt
Expedia
$85 Saint Charles, Illinois Save in Saint Charles: Book 3 Nts in Oct Fr $85+/Nt
Expedia
$77 Fairview Heights, Illinois Oct deal: Four Points by Sheraton Fairview Heights Fr $77+/Nt
Expedia
$104 Hoffman Estates, Illinois Book in Hoffman Estates: Save this Oct Fr $104+/Nt
Expedia
$50 Springfield, Illinois Save Big This Oct! Book 3 Nts in Springfield Fr $50+/Nt
Expedia
$100 Collinsville, Illinois Collinsville Savings! Book 3 Nts in Oct Fr $100+/Nt
Expedia
$64 Springfield, Illinois Save in Springfield: Book 3 Nts in Oct Fr $64+/Nt
Save with Expedia, $16/night less
$76 Rockford, Illinois Book 3 Nts in Rockford this Oct Fr $76+/Nt
Expedia
$116 Gurnee, Illinois Book 3 Nts in Gurnee this Oct Fr $116+/Nt
Expedia
$96 Rosemont, Illinois Oct deal: Sheraton Chicago O'Hare Fr $96+/Nt
Expedia
$68 Springfield, Illinois Northfield Inn & Suites Springfield in Oct: $68 & Up
Save with Expedia, $30/night less
$86 Burbank, Illinois BEST WESTERN Inn & Suites - Midway Airport in Oct: $86 & Up
Save with Expedia, $21/night less
$85 Jacksonville, Illinois Hampton Inn Jacksonville in Oct: $85 & Up
Expedia
$149 Bloomingdale, Illinois Small budget: Stay in Bloomingdale this Oct Fr $149+/Nt
Expedia
$123 Evanston, Illinois Book 4-Star Hilton Orrington/Evanston Fr $123+/Nt
Expedia
$93 Normal, Illinois Hampton Inn & Suites Bloomington-Normal in Oct: $93 & Up
Expedia
PRICEDESTINATIONDEAL
$149 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$207 New York City, New York Cheap Flights from Detroit
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$297 New York City, New York Cheap Flights from Portland
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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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