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- $15.95A View from the River: The Chicago Architecture Foundation River Cruise aboard Chicago's First Lady CruisesAmazon
- SAVE $5.91$26.08$31.99Chicago's WLS RadioAmazon
- $29.95Chicago's Fabulous FountainsAmazon
- $20.00Chicago's Chinatown By Franklin McmahonEtsy
- $54.99Chicago's Ultimate City Bike TourViator
- $71.99Chicago's Bridge Wall MuralWayfair
- SAVE $2.76$7.22$9.98Chicago's Avant TodayAmazon
- SAVE $1.93$30.06$31.99Chicago's Nurse ParadeAmazon
- $5.99Chicago's Tender FellasAmazon
- SAVE $19.75$56.23$75.98Chicago's Only CastleAmazon
- $2.99Chicago's HeadmistressAmazon
- $80.00Chicago's Black American historical bus tourViator
- SAVE $6.47$18.52$24.99Chicago's Gold Coast (Images of America)Amazon
- $52.24Chicago’s Redevelopment Machine and Blues ClubsAmazon
- $79.99Chicago's Chinatown Food and Walking TourViator
- $71.66Chicago's Lake Michigan Plated Lunch CruiseViator
- $10.99Chicago's Loop: A New Walking TourAmazon
- $21.30Chicago's Navy Pier Centennial Wheel TicketViator
- $7.27Chicago's Best Restaurants by Sherman KaplanBetter World Books
- $12.99Chicago's Polish Downtown (Images of America)Amazon
- $45.00Chicago's Original Gangster Tour by BusViator
- $7.57Chicago's Classiest Cuisine by Ann GerberBetter World Books
- $29.00Chicago's Secret Interiors Architectural Walking TourViator
- $299.95Chicago's Best Seller Angus Beef SteaksSaks Fifth Avenue
- $89.99Chicago's West Side Foodie Ride Bike TourViator
- $9.73and upChicago's Horse Racing Venues by Kimberly A. RinkerBetter World Books & 1 more
- $12.88Chicago's premium cheese pizza in double packSam's Club
- $188.00Chicago's Buckingham Fountain 1927 Framed Art | AEtsy
- $9.99Chicago's Horse Racing Venues (Images of America)Amazon
- $3.98Chicago's Loop by Heather Olivia, Knox, Janice BelcherBetter World Books
- $136.00Chicago's World Fair 1893 Ferris Wheel - Columbian ExpositionEtsy
- $6.95Chicago's Dark Side Self-Guided Smartphone Walking TourViator
- $63.00Chicago's Delicious Donut Adventure with Underground Donut TourViator
- $5.73Chicago's Polish Downtown by Victoria, Polish Museum of America, Polish Museum GranackiBetter World Books
- $89.00Chicago's Navy Pier Firework Sail Aboard a Tall ShipViator
- $11.74Chicago's South Side Irish Parade by , Bridget Houlihan KennedyBetter World Books
- $38.99'Chicago's Soldier Field' Print Poster by Darryl Vlasak Framed MemorabiliaWayfair
- $39.99Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street BeachViator
- $89.00Chicago’s Friday Night Pirates Pub Sail Aboard a Tall ShipViator
- $32.00Chicago's Midway, Movies, and the 1893 World's Fair Walking TourViator
- SAVE $5.93$19.06$24.99Chicago's Opulent Age 1870s-1940s in Vintage Postcards (IL) (Postcard History Series)Amazon
- $14.44Chicago's 1893 World's Fair by David, Di Cola, Joseph M. StoneBetter World Books
- $35.99and upChicago's Soldier Field Artwork by Darryl Vlasak Photographic Print on Wrapped CanvasWayfair & 1 more
- $5.63and upChicago's Big Teams : Great Moments of the Cubs, Bears, White Sox, Blackhawks and Bulls by Lew FreedmanBetter World Books & 1 more
- $5.14Chicago's Best Dive Bars : Drinking and Diving in the Windy City by Jonathan StocktonBetter World Books
- $5.14Chicago's Maxwell Street by Lori, Maxwell Street Historic Preservation Coalition Staff, Kamedulski, Laura GroveBetter World Books
- $35.00Chicago's World Fair 1833 - 1933 Vintage Poster Wall Art Canvas Print Home Decor Paper Reproduction Retro PaintingEtsy
- $5.99Cubsessions: Famous Fans of Chicago's North Side Baseball TeamAmazon
- $17.99Slaughterhouse: Chicago's Union Stock Yard and the World It MadeAmazon
- $2.99Baked Chicago's Simply Decadent Brownies CookbookAmazon
- $10.99Final Strike (Chicago's Finest)Amazon
- $5.99Mothman Dynasty: Chicago's Winged HumanoidsAmazon
- $253.19Echoes of Elegance: Chicago’s Architectural SplendorsViator
- $54.99Bike Tour of Chicago's Lakefront NeighborhoodsViator
- $539.99'Just Visited… Chicago's Art Institute!' Vintage AdvertisementWayfair
- $317.04Walking Tour of Chicago’s Artsy Cultural LandmarksViator
- $12.99Randhurst: Suburban Chicago's Grandest Shopping Center (Landmarks)Amazon
- $45.00Inside Tour of Chicago’s Fine Arts BuildingViator
- SAVE $3.15$21.84$24.99Avondale and Chicago's Polish Village (Images of America)Amazon
- $5.00Buena Park: Chicago's First North Shore: Buena AvenueAmazon