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A man making hats

Made with Pride in Chicago

Arts, Culture & History

3 Days 63 Miles


Downtown, Southside, North, Northwest Side, West Side

Discover All Things Chicago Made

Metropolitan style & artistry meets midwestern grit.

Chicago's more than the hog butcher and tool maker for the world. It's also the hatmaker for blockbuster movies, jean designer for ethical fashionistas, and fine chocolatier for chocolate lovers everywhere. So grab a bite, a drink, a new outfit and more as you discover all things Chicago-made. And don't forget to drop by some of the can't-miss local attractions.

Day 1:

Downtown & Southside

  • Exterior of the Robie House.

Start your day downtown with coffee and fresh, classic donuts from Do-Rite Donuts (IM), a local gem that offers a variety of creative flavors and delicious Chicago-made coffee. Then, make your way over to Scratch Goods (IM) and peruse simple, natural skincare products produced by a pair of high school best friends turned entrepreneurs. The space’s vibe is modern and relaxing, and it’s home to Chicago’s first mask bar!

Even if you’re not a hat person, it’s worth stopping at Optimo Hats (IM) to see handcrafted apparel that has graced the heads of Hollywood stars like Ben Affleck and Johnny Depp. Staying true to his roots, owner Graham Thompson’s original hat designs are inspired by the city he loves, with names like The Rush Street and The Hyde Park.

Lunch will be more than a meal — it will be a celebratory experience. Located in legendary architect Daniel Burnham's Railway Exchange, The Exchange showcases a remarkable collection of dishes by James Beard-nominated Chef Brian Huston and decorated Head Baker Matt Pontarelli. From fresh local produce to steaks, seafood and creative cocktails, this Instagrammable spot has something for everyone.

Heading south, head down to Wild Blossom Meadery and Winery (IM), the only meadery on the Northern Illinois Wine Trail, to sample some of the Midwest’s finest honey wines and meads. This South Side fixture prides itself on crafting beverages sustainably using local ingredients. On your way to Hyde Park, swing by Brown Sugar Bakery (IM) for Stephanie Hart’s famous caramel cake or one of her other “dangerously delicious” sweet treats. Brown Sugar also has a Navy Pier location, in case you’d prefer to visit earlier in the day while you’re enjoying downtown.

When you arrive in Hyde Park, treat yourself to the architectural masterpiece and UNESCO World Heritage Site that is Frank Lloyd Wright’s Frederick C. Robie House. Take a guided tour of the legendary home, which the American Institute of Architects named one of the 10 most significant buildings of the 20th century.

If you’re in the mood for a museum, you’re in the right place. The Smart Museum of Art houses a collection of more than 7,500 objects that explore diverse identities, experiences, and ideas. Or perhaps you’d like to expand your knowledge of extraordinary natural phenomena like tornadoes, lightning, fire, tsunamis, avalanches, and atoms in motion — in which case the Museum of Science and Industry is the place to be. With exhibits like the U-505 Submarine, United's Boeing 727 Airplane, Henry Crown Space Center, and Colleen Moore's Fairy Castle, you’ll experience everything from mind-blowing wonders to new frontiers you didn’t know existed.

Dinner at Virtue Restaurant (IM) is going to be a special experience — one look at Chef Erick Williams’ resume makes that abundantly clear. It includes “best new restaurant” awards from national outlets like Eater and Esquire, a Game Changer Award from the Chicago Tribune, and a semifinalist nomination for the James Beard Foundation's Best Chef (among other accolades).

After a long day of adventuring, check out the Hyde Park nightlife or hit the hay at Sophy Hotel, a beautiful boutique that reflects the authenticity, artsiness, and energy of the neighborhood itself.

Day 2:

North & Northwest Side

  • Welcome sign Andersonville.

Get a jump on the morning in the Lincoln Square neighborhood at Baker Miller (IM), a James Beard-nominated cafe with a cozy coffee-shop feel. Fuel up on rich coffee and an array of exquisitely crafted breakfast items, including bagel sandwiches, breakfast tacos, pastrami hash, and freshly-baked pastries.

Extend the morning with a stroll along Clark Street in Andersonville, one of the North Side’s delightfully quirky neighborhoods. Pop into Dearborn Denim (IM) — home to some of the most comfortable, durable, American-made jeans around — and allow the friendly staff to make custom adjustments for you in the store. Once you depart with a new pair of perfectly-fitting pants, check out the nearby Swedish American Museum to get a sense of the neighborhood’s Scandinavian roots.

Next, proceed to Avondale, an under-the-radar Northwest Side community dotted with down-to-earth bars, old-school venues, and interesting shops. Spend some time at You Are Beautiful (IM), a studio that doubles as a storefront for artist and designer Matthew Hoffman. Art, clothing, and crafts are available for purchase, and don’t forget to pick up one of his “you are beautiful” stickers, which have helped spread his message of positivity across the globe.

For a burst of Mexican flavor, grab some midafternoon tacos at Cafe Tola’s (IM) Avondale cafe, and, if you have room, taste one of their out-of-this-world empanadas. Wash down lunch with your favorite style of beer at Revolution Brewing (IM), the state’s largest craft brewery. The cavernous taproom — with its gleaming tanks, rustic tables, and retro popcorn machine — offers an authentic Chicago brewery experience.

If you have time, stop by Swoon Living (IM), an alluring shop offering exceptional wine glasses, decanters, and cocktail glasses. Also nearby is Katherine Anne Confections (IM), where you can indulge in sugary delights like their famous, super-thick hot chocolate.

It’s time to stretch those legs. Bask in an urban wilderness as you walk the 606, an elevated trail enclosed in greenery interspersed with glorious city views. This will lead you to the popular Wicker Park/Bucktown area, where you’ll sit down for dinner and drinks at Piece Pizza (IM). Known for its New Haven-style pies (and an appearance on MTV’s Real World Chicago), this restaurant and brewery is a favorite of locals and visitors alike.

Nightlife lovers can grab a drink, (and maybe even a show!) at The Den Theater, a multi-stage venue featuring multiple bars serving up specialty cocktails, herbal teas, and killer lattes. Just steps away, rest up at The Robey, an architectural jewel and the area’s only skyscraper. Fancy a nightcap? Head to the top floor lounge, and wind down with views of a city approaching its slumber.

Day 3:

West Side

  • Indoor Greenhouse.

To perk up in the morning, break your fast at Ipsento Coffee (IM), where you can enjoy small-batch roasted coffee, house-made mini donuts or a delectable bacon cheddar rosemary scone. You’re in good hands — the Daily Meal has recognized Ipsento as one of the nation’s 50 best coffee shops.

Venture out to Garfield Park on the West Side to experience the third largest garden-under-glass in the world. The Garfield Park Conservatory, which spans 12 acres of indoor and outdoor gardens, is a national botanical treasure filled with colorful tropical flowers, palm trees and more luscious greenery than you can imagine.

Before leaving the area, be sure to stop by Bright Endeavors (IM) to peruse hand-poured candles that are as aromatic as they are lovely. Plus, by supporting Bright Endeavors, you’ll be supporting job training programs for local young mothers.

Get lunch in West Town at Forbidden Root Brewery & Restaurant (IM), Chicago’s first botanical brewery, which serves up creative dishes like duck and dumplings and steelhead trout. The beers, many brewed with rare wild ingredients, will likely be unlike any you’ve ever tasted.

End your trip on a sweet note at Black Dog Gelato (IM) by experimenting with fun, limited-time flavors like sesame chocolate chip and brown butter salted caramel brownie.

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