Live Like a Local in Chicago: Beyond Downtown

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Advisor - Morgan Dowling
Curated By

Morgan Dowling

  • Arts & Culture

  • City Travel

  • Food & Wine

  • Chicago

  • Lakeside

Advisor - Live Like a Local in Chicago: Beyond Downtown
Curator’s statement

Every visitor to Chicago has an idea in their head of what the city has to offer. Michigan Avenue, Navy Pier, Millennium Park. But what about after you’ve been there, done that? This is your guide to exploring what the city has to offer when you venture out of the downtown bubble. Discover unique, cultural and hidden gem neighborhoods with shops and restaurants that put the Mag Mile to shame.

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Where to stay in Chicago

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Things to do in Chicago

Ping Tom Memorial Park, Chinatown

Logan Square

Festive Collective: The go-to destination for gifts, celebrations and nostalgia.

Lost Girls: A women and minority-owned shop voted best vintage in Chicago.

Logan Square Farmers Market: A year-round Sunday market with local produce and live entertainment.

Wicker Park

Penelope's: A relaxed clothing boutique with a selection of casual, comfortable looks for men and women.

Wilderhouse: A shop with an organic, natural vibe that features clothing, apothecary and home goods.

Big Mini Putt Club: An old-school indoor mini-golf bar and lounge with board games and craft cocktails.

Lincoln Park

Art Effect: An eclectic boutique with endless options of funky apparel, homeware and decor.

Left on Thred: A curated collection of everyday essentials with a healthy mixture of classic and on-trend items.

Lincoln Park Zoological Gardens - the second-oldest zoo in the US, 35 acres of all things wildlife. It's a highlight for visitors of all ages.

West Loop

Primitive: A 4-story showroom featuring global antique and modern furniture, art, jewelry and fashion.

Notre: A men's boutique with a an airy, minimalist vibe.

Randolph Street Market: An antique market that's been around since 2003 and features indie designers, modern vintage and holiday markets.

Chinatown

King Karaoke Chicago: A karaoke bar with private, themed rooms where you can dance and sing the night away with friends

Ping Tom Memorial Park: Situated along the South branch of the Chicago River, this park features unique Asian architecture, walking trails and a playground

Pilsen

Pilsen Vintage: An 18th Street vintage clothing boutique with quirky finds

El Anticuario: A shop where you can find anything from pastries to rare books to decor

Everything Store: A store that curates a combination of vintage, antique goods and small business-made wares

Places to eat & drink in Chicago

Logan Square

Daisies: A beloved local pasta shop with favorites like gnocchi, beet agnolotti and scrambled egg bruschetta.

Giant: A James Beard finalist chef serves up neighborhood faves like jalapeño biscuits, feta in phyllo and drunken beef.

Lula Café: An all-day dining destination with a fabulous wine list and Chicago's only James Beard Award winner in 2024 for Outstanding Hospitality.

Wicker Park

Taxim: A charming Greek restaurant with a rooftop space and delicious gyros.

Antique Taco: A stylish and creative Mexican restaurant with counter service and delicious horchata milkshakes.

Schwa: A Michelin-starred spot that offers a truly unique culinary experience.

Lincoln Park

Galit: Middle Eastern dishes with a modern flare, helmed by two-time James Beard Award-winning chef Zach Engel.

Ranalli's: A neighborhood favorite pizzeria and bar with a lively patio and overall fun vibes.

Esmé: Michelin-starred restaurant that completely transforms every 12 weeks, providing an ever-fresh experience for locals.

West Loop

La Josie: A family-owned joint with a high-end Latin-focused menu.

Monteverde: Helmed by Top Chef alum Sarah Grueneberg, this pasta place has been open for 10 years and is still somewhere you have to fight for a reservation.

J.P. Graziano: Yes, it's just a sandwich shop — but it is the sandwich shop to indulge in when in the Windy City.

Chinatown

MingHin: A massive dim-sum restaurant serving up both traditional and modern Cantonese.

Go 4 Food: Don't let the name or façade fool you — this "hole in the wall" spot is recognized by the Michelin Guide, Thrillist and other industry voices.

Chiu Quon Bakery: The oldest Chinese bakery in the city is at the top of everyone's Chinatown to-do list.

Pilsen

HaiSous: James Beard-nominated Vietnamese kitchen recognized as one of Chicago Magazine's Best Restaurants — what's not to love?

La Luna: A women-owned Mexican joint located on Pilsen's famous 18th Street where you can take a tortilla-making class.

Pilsen Yards: One of the best winterized patios in the city (think literal heated floors) makes this a year-round destination for cocktails and live music.

Need to know

In a city like Chicago, new experiences are endless—especially when you venture away from the city center. All of these neighborhoods are so accessible via public transportation, some only mere minutes from The Loop. Step out of your comfort zone and have a more authentic, cultural and community-driven experience in one of the country's largest cities.

Advisor - Morgan Dowling

Travel Advisor

Morgan Dowling

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