The Ultimate Chicago Pumpkin Checklist ✔️

Every pumpkin dish you should try to keep you cozy all season long.

📸 Anjali Pinto

First Slice Pie Cafe: PUMPKIN PIE

Andersonville + Ravenswood + Albany Park

Simple cafe specializing in fruit and cream-filled pies, along with quiche, sandwiches + salads.

 


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Hoosier Mama Pie: PUMPKIN PIE

East Village

A rotating menu of homemade sweet and savory pies on offer in a cute shop with a retro look.

 


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DB3 Donuts: PUMPKIN SPICE GLUTEN FREE DONUTS

Evanston

Gourmet donuts and fresh roasted organic coffee serving Chicago’s North Shore.

 


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Hewn: PUMPKIN WHOOPIE PIES

Evanston

Bakery offering made-from-scratch bread, pastries + sandwiches in a warm, rustic space.

 


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Joe’s Imports: PUMPKIN SPICE “WHITE GIRL WASTED” COCKTAIL

Fulton Market

Stylish, low-lit hangout with an extensive wine selection to pair with inventive pub plates + pasta.

 


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Tavern On Rush: PUMPKIN PIE PANCAKES

Gold Coast

Steakhouse fare, nightly DJs + outdoor seating define this lively, upscale restaurant.

 


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Sprinkles Cupcakes: PUMPKIN CUPCAKES

Gold Coast

Cheery bakery known for its rotating menu of cupcakes, ice cream + cookies.

 


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Westons Coffee + Tap: PUMPKIN SPICE DONUTS + “SMASHING PUMPKIN” LATTE

Jefferson Park

European inspired coffee shop serving Metropolis Coffee, espresso based beverages, craft beer and wine, fresh pastries + made to order deli sliced sub sandwiches.

 


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Maison Parisienne: PUMPKIN RELIGIEUSE + MACARONS + PUMPKIN SPICE LATTE

Lakeview

French cafe offering classic fare + baked goods with coffee and tea in simple storefront environs.

 


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Southern France Patisserie: PUMPKIN SPICE PETIT GATEAU

Lakeview

French-inspired pastries served with Southern hospitality.

 


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Sapori Trattoria: PUMPKIN RAVIOLI + STUFFED MINI PUMPKIN APPETIZER

Lincoln Park

Small neighborhood restaurant with housemade pasta + other classic Italian dishes.

 


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Summer House Santa Monica: PUMPKIN CHIFFON PIE

Lincoln Park

Sunny restaurant serving New American grub, tropical drinks + more in an airy space with an atrium.

 


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Vanille Patisserie: PUMPKIN CHEESECAKE W/ GINGERSNAP CRUST + PUMPKIN MACARONS

Lincoln Park + Lakeview + Hyde Park + West Loop

Luxe pastry shop crafting macarons, petit fours and other French confections, plus custom cakes.

 


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Sweet Mandy B’s: PUMPKIN CABINET PUDDING

Lincoln Park

Welcoming bakeshop for old-fashioned treats from cupcakes + pies to cookies, plus breakfast bites.

 


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Blue Door Farm Stand: PUMPKIN SPICE BOURBON CAKE

Lincoln Park

Homey farm-to-table cafe with American eats and cold-pressed juice as well as home + pantry items.

 


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Stax Cafe: PUMPKIN SPICE PANCAKES

Little Italy + River West

Casual eatery serving breakfast classics all day plus fresh juice, smoothies + a small lunch menu.

 


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SABA Italian Bar + Kitchen: PUMPKIN CHEESECAKE

Logan Square

Modern Italian cuisine + cocktails are dished out in a stylish setting with ample living greenery.

 


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Pretty Cool Ice Cream: PUMPKIN “PIECICLES”

Logan Square

Easygoing, family-friendly pick for rotating popsicles, custard + plant-based ice cream novelties.

 


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The Chicago Diner: PUMPKIN PIE SHAKE

Logan Square

Hearty plates of diverse vegetarian + vegan diner fare dished out in sleek, casual surrounds.

 


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Bang Bang Pie + Biscuits: PUMPKIN PIE

Logan Square + Ravenswood

Rustic bakery with a rotating menu of homemade sweet and savory pies + biscuits for eat-in or takeout.

 


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90 Miles Cuban Cafe: PUMPKIN FLAN

Logan Square + Roscoe Village + Lincolnwood

Cubanos, empanadas, ropa vieja and more in a casual, colorful space with murals, patio + BYOB policy.

 


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Stan’s Donuts: PUMPKIN DONUTS + PUMPKIN PIE LATTE

Millennium Park + Mag Mile + Streeterville + Gold Coast + South Loop + West Loop + Wicker Park + Lakeview

Stylish spot supplying gourmet donuts, milkshakes, hot coffee drinks + cold brew on tap.

 


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Big Bowl: PUMPKIN CHEESECAKE

River North

Restaurant serving Chinese and Thai dishes, cocktails + craft beers in a relaxed, stylish space.

 


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La Bodega: CHURRO PUMPKIN SPICE DIPPING SAUCE

River North

Elevated convenience store with a gourmet taco window, specialty churros, imported foods + liquor.

 


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Aba: PUMPKIN HUMMUS

River North

Posh destination for elevated Mediterranean fare + cocktails, plus a lounge-style rooftop patio.

 


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Mercadito: “#BASICJUICE” PUMPKIN SPICE COCKTAIL

River North

Cocktails and upscale Mexican eats keep this popular hangout bustling with a hip, young crowd.

 


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Mity Nice Bar + Grill: PUMPKIN CHIFFON PIE

River North

Inside Water Tower Place, this sleek eatery serves American fare, including complimentary popovers.

 


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Wildfire Chicago: PUMPKIN PIE

River North

Bustling, upscale eatery featuring steak + other New American fare in a spacious, polished interior.

 


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Mastro’s Steakhouse: PUMPKIN BUTTER CAKE

River North

Outpost of the Arizona chain serving an abundance of meat + martinis in posh, bi-level environs.

 


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Union Sushi + Barbeque Bar: PUMPKIN MOCHI CAKE

River North

Trendy, bustling restaurant with an upscale-urban vibe and a creative take on Japanese cuisine.

 


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Beatrix: PUMPKIN PANCAKES + PUMPKIN CREAM NITRO COFFEE

River North, Streeterville, Fulton Market, + The Loop

Modern, all-day venue combining an American eatery, wine and cocktail bar + a bakery/cafe.

 


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Justice of the Pies: PUMPKIN PRALINE PIE

Riverwalk South (between Michigan + Wabash)

Bakery that specializes in sweet and savory pies, quiches + tarts.

 


 

BienMeSabe Venezuelan Cafe & Restaurant: PUMPKIN SOUP

Sheridan Park

Unassuming eatery featuring traditional Venezuelan grub, including empanadas, arepas + plantains.

 


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Goddess + the Baker: PUMPKIN CHEESECAKE

The Loop

All-day cafe with baked goods plus breakfast items, salads, sandwiches, flatbreads + beer and wine.

 


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Magnolia Bakery: PUMPKIN CUPCAKES + PUMPKIN GINGERSNAP COOKIES + PUMPKIN GINGERSNAP BANANA PUDDING

The Loop

Global chain featuring sweets like cupcakes, cheesecake + banana pudding in a vintage setting.

 


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Toni Patisserie Cafe: PUMPKIN CAKE

The Loop

Bakery/cafe offering from-scratch French-style sweets and savories for dine-in or takeout.

 


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Tikka N’ Curry: PUMPKIN SPICE LASSI

The Loop

Modern cafe where patrons choose their own ingredients for bowls and wraps of Indian fare.

 


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Wow Bao: PUMPKIN BAO

The Loop + Gold Coast + Michigan Avenue + Lakeview + Water Tower Place

Inventive baozi (steamed, filled buns) + other Chinese dishes ordered via touch screens.

 


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Eden: PUMPKIN COCKTAIL

United Center

Creative New American fare with Mediterranean influences pairs with craft cocktails in a chic space.

 


 

Bonci Pizzeria: PUMPKIN PIZZA W/ SAUSAGE + PROVOLONE

West Loop + Wicker Park

Rome-based Italian import selling scissor-cut slices featuring distinctive toppings, sold by weight.

 


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La Sardine: PUMPKIN POT DE CREME

West Loop

Classic French comfort food + drinks are served in this casual, wood-trimmed space.

 


 

Mart Anthony’s: STUFFED PUMPKIN

West Loop

Neighborhood restaurant and steakhouse serving traditional Italian favorites + cocktails since 1981.

 


 

Kuma’s Corner: SPIKED PUMPKIN SPICE LATTER COCKTAIL

West Loop

Busy pub known for its long list of creative burgers + rock ‘n’ roll soundtrack.

 


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West Town Bakery: PUMPKIN DONUTS + SCONES + PUMPKIN SPICE LATTE

West Town

Sustainable bakery serving organic goodies, breakfast fare, coffee + sandwiches.

 


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Cafe Robey: PUMPKIN SOUP

Wicker Park

Cafe at The Robey hotel offering American fare for brunch + dinner, plus a cocktail lounge upstairs.

 


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Eli’s Ark: PUMPKIN ICE CREAM

Wicker Park

Dessert shop offering animal-inspired gelato cones.

 


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Wynwood: PUMPKIN SPICE FROZEN SLUSHY

Wicker Park

Hip, graffiti-lined spot for creative American cooking with craft cocktails on tap plus a patio.

 


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Kit Kat Lounge & Supper Club: PUMPKIN PIE “FALLTINI”

Wrigleyville

Drag-queen divas perform nightly at this upscale American restaurant with a lengthy cocktail menu.

 


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Benny’s Chop House: PUMPKIN SPICE VODKA

Streeterville

High-end contemporary steakhouse serving aged steaks, seafood + pasta with piano music most nights.

 

 

 

tags: fall, autumn, seasonal, season, drinks, dishes, food, cocktails, halloween, holiday, pumpkin, sweet, dessert, theme, themed

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