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Chicago, IL Travel Deals

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Chicago, IL Travel Deals

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TYPE PRICE DESTINATION DEAL
$161 Chicago, Illinois Save in Chicago: Book 3 Nts in Oct Fr $161+/Nt
Expedia
$90 Chicago, Illinois $90 & Up: Chicago's Essex Inn 3-Star Hotel in Chicago
Save with Expedia, $16/night less
$84 Chicago, Illinois Red Roof Inn Chicago Downtown Magnificent Mile in Oct: $84 & Up
Save with Expedia, $21/night less
$115 Chicago, Illinois Special deal: 4-Star theWit - A DoubleTree by Hilton Fr $115+/Nt
Expedia
$108 Chicago, Illinois Save at 4-Star Raffaello: $108 & Up in Oct
Save with Expedia, $58/night less
$68 Chicago, Illinois Chicago Savings! Book at Travelodge Chicago Downtown Fr $68+/Nt
Expedia
$124 Chicago, Illinois Small budget: Book W Chicago Lakeshore 3 Nts in Oct Fr $124+/Nt
Expedia
$81 Chicago, Illinois Save at 3.5-Star River: $81 & Up in Oct
Save with Expedia, $8/night less
$147 Chicago, Illinois Book 4-Star Palomar Chicago, a Kimpton Fr $147+/Nt
Save with Expedia, $26/night less
$138 Chicago, Illinois Save at 3-Star Holiday Inn Chicago O'Hare: $138 & Up in Oct
Expedia
$116 Chicago, Illinois Chicago Savings! Book at Holiday Inn Express Cass Fr $116+/Nt
Expedia
$114 Chicago, Illinois Book 3 Nts in Chicago this Oct Fr $114+/Nt
Expedia
$157 Chicago, Illinois $157 & Up: PUBLIC Chicago 4-Star Hotel in Chicago
Save with Expedia, $38/night less
$139 Chicago, Illinois Small budget: Stay in Chicago this Oct Fr $139+/Nt
Expedia
$109 Chicago, Illinois Save at 3-Star Holiday Inn Chicago Downtown: $109 & Up in Oct
Expedia
$109 Chicago, Illinois Save Big This Oct! Book 3 Nts in Chicago Fr $109+/Nt
Expedia
$99 Chicago, Illinois Book the Hostelling International Chicago 3 Nts in Oct Fr $99+/Nt
Expedia
$134 Chicago, Illinois Oct deal: Holiday Inn Chicago Mart Plaza River North Fr $134+/Nt
Expedia
$109 Chicago, Illinois Chicago Savings! Book 3 Nts in Oct Fr $109+/Nt
Expedia
$91 Chicago, Illinois Chicago Savings! Book at Warwick Allerton Chicago Fr $91+/Nt
Save with Expedia, $73/night less
$90 Tinley Park, Illinois Book 3 Nts in Tinley Park this Oct Fr $90+/Nt
Expedia
$98 Lombard, Illinois Save at 3-Star Hyatt Place Chicago/Lombard: $98 & Up in Oct
Expedia
$79 Oakbrook Terrace, Illinois Oct deal: Hilton Garden Inn Oakbrook Terrace Fr $79+/Nt
Expedia
$51 Bridgeview, Illinois Oct deal: Super 8 Bridgeview/Chicago Area Fr $51+/Nt
Save with Expedia, $12/night less
$199 Evanston, Illinois Book 3-Star BEST WESTERN University Plaza in Evanston Fr $199+/Nt
Expedia
$66 Arlington Heights, Illinois Book in Arlington Heights: Save this Oct Fr $66+/Nt
Save with Expedia, $22/night less
$88 Deerfield, Illinois Hyatt Deerfield on Sale: Book 3 Nts in Oct Fr $88+/Nt
Save with Expedia, $21/night less
$117 Evanston, Illinois Hilton Orrington/Evanston in Oct: $117 & Up
Expedia
$76 Wood Dale, Illinois Save in Wood Dale: Book 3 Nts in Oct Fr $76+/Nt
Expedia
$107 Willowbrook, Illinois Oct deal: Champagne Lodge and Luxury Suites Fr $107+/Nt
Save with Expedia, $28/night less
$156 Bloomingdale, Illinois Oct deal: Residence Inn Chicago Bloomingdale Fr $156+/Nt
Expedia
$104 Orland Park, Illinois Book 3 Nts in Orland Park this Oct Fr $104+/Nt
Expedia
$130 Evanston, Illinois Save in Evanston: Book 3 Nts in Oct Fr $130+/Nt
Expedia
$117 Tinley Park, Illinois Oct deal: Hilton Garden Inn Chicago/Tinley Park Fr $117+/Nt
Expedia
$99 Oakbrook Terrace, Illinois Special deal: 3.5-Star Hilton Chicago Oak Brook Suites Fr $99+/Nt
Expedia
$99 Downers Grove, Illinois Book 3 Nts in Downers Grove this Oct Fr $99+/Nt
Expedia
$96 Crestwood, Illinois Oct deal: Holiday Inn Express Crestwood Fr $96+/Nt
Expedia
$889 Lombard, Illinois Lombard 4-Star Hotel Sale! 3 Nts + Air Fr $889
Expedia
$99 Northbrook, Illinois Book the Hilton Northbrook 3 Nts in Oct Fr $99+/Nt
Expedia
$90 Bloomingdale, Illinois Oct deal: Hilton Chicago/Indian Lakes Fr $90+/Nt
Expedia
$76 Arlington Heights, Illinois DoubleTree by Hilton Chicago - Arlington Heights in Oct: $76 & Up
Expedia
$128 Bedford Park, Illinois Hampton Inn Chicago-Midway Airport in Oct: $128 & Up
Expedia
$149 Oak Brook, Illinois Book 4-Star The Hyatt Lodge at McDonald's Campus Fr $149+/Nt
Expedia
$135 Arlington Heights, Illinois Save in Arlington Heights: Book 3 Nts in Oct Fr $135+/Nt
Expedia
$88 Rosemont, Illinois Hyatt Regency O'Hare in Oct: $88 & Up
Expedia
$89 Rosemont, Illinois Book 3.5-Star Hilton Rosemont / Chicago O'Hare Fr $89+/Nt
Expedia
$73 Schiller Park, Illinois Hampton Inn Chicago-O'Hare International Airport in Oct: $73 & Up
Save with Expedia, $19/night less
$105 Bolingbrook, Illinois Book in Bolingbrook: Save this Oct Fr $105+/Nt
Expedia
$126 Oak Brook, Illinois Save Big This Oct! Book 3 Nts in Oak Brook Fr $126+/Nt
Expedia
$88 Rosemont, Illinois Rosemont Savings! Book 3 Nts in Oct Fr $88+/Nt
Save with Expedia, $21/night less
$132 Skokie, Illinois Book 3-Star Holiday Inn Chicago North Shore (Skokie) Fr $132+/Nt
Expedia
$79 Gurnee, Illinois Book in Gurnee: Save this Oct Fr $79+/Nt
Expedia
$89 Schaumburg, Illinois Comfort Suites Schaumburg
Groupon Inc
$102 Aurora, Illinois Book 3 Nts in Aurora this Oct Fr $102+/Nt
Expedia
$90 Merrillville, Indiana Oct deal: Hilton Garden Inn Merrillville Fr $90+/Nt
Expedia
$109 McHenry, Illinois Oct deal: Hampton Inn - McHenry Fr $109+/Nt
Expedia
$97 Merrillville, Indiana Save Big This Oct! Book 3 Nts in Merrillville Fr $97+/Nt
Expedia
$63 Naperville, Illinois Book in Naperville: Save this Oct Fr $63+/Nt
Expedia
$66 Schaumburg, Illinois Special deal: 3-Star Hilton Garden Inn Schaumburg Fr $66+/Nt
Expedia
$100 Deer Park, Illinois Hampton Inn and Suites Chicago Deer Park in Oct: $100 & Up
Expedia
$95 Portage, Indiana Small budget: Stay in Portage this Oct Fr $95+/Nt
Expedia
$104 Warrenville, Illinois Oct deal: HYATT house Chicago/Naperville/Warrenville Fr $104+/Nt
Expedia
$1,261 Schaumburg, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Schaumburg Fr $1,261
Expedia
$86 Lake Forest, Illinois Book 3 Nts in Lake Forest this Oct Fr $86+/Nt
Expedia
$47 Saint Charles, Illinois Book 3-Star Pheasant Run and Convention Center Fr $47+/Nt
Save with Expedia, $16/night less
$117 Alsip, Illinois Save at 3.5-Star Doubletree Chicago / Alsip: $117 & Up in Oct
Expedia
$80 Champaign, Illinois Oct deal: Country Inn & Suites Champaign-North Fr $80+/Nt
Expedia
$93 Westchester, Illinois Hampton Inn Chicago/Westchester (Oak Brook) in Oct: $93 & Up
Expedia
$90 Moline, Illinois Save Big This Oct! Book 3 Nts in Moline Fr $90+/Nt
Expedia
$122 Zion, Illinois Illinois Beach and Conference Center in Oct: $122 & Up
Expedia
$99 Bloomington, Illinois Book the Doubletree By Hilton Bloomington 3 Nts in Oct Fr $99+/Nt
Expedia
$99 Bloomington, Illinois Hampton Inn Bloomington West in Oct: $99 & Up
Expedia
$76 Rockford, Illinois Rockford Savings! Book at Hampton Inn Rockford Fr $76+/Nt
Expedia
$128 Bedford Park, Illinois Book 3-Star Hilton Garden Inn Chicago Midway Airport Fr $128+/Nt
Expedia
$757 East Peoria Peoria County, Illinois East Peoria 3.5-Star Hotel Sale! 3 Nts + Air Fr $757
Expedia
$83 Glenview, Illinois Glenview Savings! Book at Wyndham Glenview Suites Fr $83+/Nt
Save with Expedia, $21/night less
$99 Skokie, Illinois Book 3.5-Star DoubleTree by Hilton Chicago North Shore Fr $99+/Nt
Expedia
$110 Addison, Illinois Save Big This Oct! Book 3 Nts in Addison Fr $110+/Nt
Expedia
$64 Springfield, Illinois Book 3-Star Hilton Garden Inn Springfield Fr $64+/Nt
Save with Expedia, $16/night less
$73 Springfield, Illinois Oct deal: Northfield Inn & Suites Springfield Fr $73+/Nt
Save with Expedia, $31/night less
$95 O'Fallon, Illinois Book in O'Fallon: Save this Oct Fr $95+/Nt
Expedia
$74 Gurnee, Illinois BEST WESTERN Gurnee & Suites in Oct: $74 & Up
Save with Expedia, $12/night less
$76 Warrenville, Illinois Hilton Garden Inn Naperville/Warrenville in Oct: $76 & Up
Expedia
$400 Normal, Illinois Normal 3.5-Star Hotel Sale! 3 Nts + Air Fr $400
Expedia
$73 Hoffman Estates, Illinois Oct deal: Hampton Inn & Suites Hoffman Estates Fr $73+/Nt
Expedia
$86 Des Plaines, Illinois Oct deal: Hilton Garden Inn Chicago O'Hare Airport Fr $86+/Nt
Expedia
$96 Deerfield, Illinois Oct deal: Chicago Marriott Suites Deerfield Fr $96+/Nt
Save with Expedia, $23/night less
$144 Oak Lawn, Illinois Book 3.5-Star Hilton Chicago/Oak Lawn Fr $144+/Nt
Expedia
$93 Rosemont, Illinois Book in Rosemont: Save this Oct Fr $93+/Nt
Expedia
$95 Rosemont, Illinois Doubletree Chicago O'Hare Airport - Rosemont in Oct: $95 & Up
Expedia
$74 Countryside, Illinois Oct deal: BEST WESTERN Chicagoland - Countryside Fr $74+/Nt
Save with Expedia, $19/night less
$81 Fairview Heights, Illinois Save Big This Oct! Book 3 Nts in Fairview Heights Fr $81+/Nt
Expedia
$52 O'Fallon, Illinois Save in O'Fallon: Book 3 Nts in Oct Fr $52+/Nt
Expedia
$143 Bloomingdale, Illinois Save Big This Oct! Book 3 Nts in Bloomingdale Fr $143+/Nt
Expedia
$85 Jacksonville, Illinois Jacksonville Savings! Book at Hampton Inn Jacksonville Fr $85+/Nt
Expedia
$1,182 Downers Grove, Illinois Save at 3.5-Star Hotel: 3 Nts + Air to Downers Grove Fr $1,182
Expedia
$96 Burbank, Illinois Oct deal: BEST WESTERN Inn & Suites - Midway Airport Fr $96+/Nt
Save with Expedia, $11/night less
$102 Matteson, Illinois Hampton Inn & Suites Chicago Southland-Matteson in Oct: $102 & Up
Expedia
$85 Saint Charles, Illinois Book 3 Nts in Saint Charles this Oct Fr $85+/Nt
Expedia
$97 Rockford, Illinois $97 & Up: Hilton Garden Inn Rockford 3-Star Hotel in Rockford
Expedia
PRICEDESTINATIONDEAL
$118 New York City, New York Cheap Flights from Washington, DC
DealBase.com
$193 New York City, New York Cheap Flights from Tampa
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$199 New York City, New York Virgin America Current Lowest Fares
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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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