Bakery · North Side
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"Open for nearly 100 years, this family-run offers seven varieties of zeppole for the holiday, all priced at $3.90, including cannoli, blueberry, peach and pineapple." - Samantha Nelson, Eater Staff
Hotel · Bucktown
Nestled in a stunning 1929 art deco building, this chic hotel boasts a rooftop pool, a lively bar, and prime access to Wicker Park's vibrant scene.
14 Postcards
Restaurant · Near North Side
"Adalina is an upscale, modern Italian restaurant in the Gold Coast, led by Michelin-starred chef and Top Chef alum Soo Ahn. The menu blends traditional Italian flavors with contemporary innovations, earning recognition for the best pasta in Chicago, complemented by a romantic ambiance and a thoughtfully curated beverage and wine program."
21 Postcards
Thai restaurant · Lakeview East
Tuk Tuk Thai Isan transports you straight to the vibrant streets of Thailand with its spicy, authentic dishes, lively decor, and welcoming vibe.
8 Postcards
Pizza restaurant · River North
Family-owned local chain for Italian classics & Chicago-style, deep-dish pizzas with buttery crusts.
Bar · South East Ravenswood
Relaxed bar & coffeehouse with a large, rotating list of beers, a photo booth & a back patio.
Bar · Humboldt Park
Craft cocktails and local brews await in a stylish, vintage hunting lodge with a cozy patio, perfect for laid-back afternoons and good company.
18 Postcards
Hot dog restaurant · Lakeview
Byron's is your go-to spot for Chicago-style hot dogs and burgers, serving up no-frills deliciousness with friendly vibes and tasty outdoor seating.
9 Postcards
Bar · Fulton River District
Kumiko offers a hip space where imaginative Japanese bites and expertly crafted cocktails create a unique and stylish experience worth indulging in.
82 Postcards
New American restaurant · River North
New American spin on British food served in an upscale restaurant with 2 bars & riverfront views.
16 Postcards
Hotel · Near North Side
Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa. Next to the Chicago River, this luxe high-rise hotel is 2 blocks from upscale shopping on the Magnificent Mile. Sleek rooms have full kitchens, floor-to-ceiling windows with city and Lake Michigan views, 42-inch flat-screen TVs, custom-stocked minibars and limestone bathrooms. Suites add marble fireplaces and bathrooms with separate showers and soaking tubs. Wi-Fi is available for a fee. Amenities include an indoor pool, a seasonal outdoor terrace, a hip bar and a 23,000-sq-ft spa. Additional perks include a gym, a salon (fee), event spaces, and a fine dining restaurant with panoramic city vistas.
4 Postcards