Exploring by neighborhood is the best way to do Chicago. If you have multiple days in the city and you only stay downtown, that’s considered a fail in the locals’ book. Same goes if you try to traverse the North Side, West Side, and South Side all at once — you’re doing it wrong. Given that Chicago has over 77 neighborhoods and community areas, a successful day trip is more than doable but requires some strategy. Take the time to align your stops and you’ll see more of any given section of the city.
Here are three itineraries that maximize the number of neighborhoods you can pack in. Each day trip focuses on one main street as a base for exploring. Map out some pinpoints and go.
Day Trip Option #1
- Neighborhoods: Wicker Park, Bucktown and Logan Square
- Route: Milwaukee Avenue, a major northwest diagonal street with several CTA Blue Line ‘L’ train stops
- Find: A slice of Chicago’s hipster scene
Just beyond downtown, these Northwest Side neighborhoods are practically an alphabet soup of all things hip and cool about Chicago — from art and architecture, to boutiques and breweries, to coffee shops and cocktail bars.
WICKER PARK | Start with a plate of Southern-inspired Mexican comfort food at Dove’s Luncheonette. This little cafe is heavy on the retro charm and has a menu loaded with satisfying AM plates like the Burnt Ends Hash and Chicken Fried Chicken. Stroll the historic mansions nearby on Hoyne and Pierce Avenues in the Wicker Park Landmark District, and if the rooftop bars at The Robey are open, get an aerial view and check out the downtown skyscrapers in the horizon. Shop along the stretch of Milwaukee Avenue between Division Street and North Avenue. There’s a solid mix of vintage and thrift shops (like Store B Vintage and Kokorokoko) plus local boutiques (Una Mae’s is a mainstay) and great record stores, bookstores and art galleries.
BUCKTOWN | Break for a beer and pizza at award-winning Piece Brewery — or if you prefer beer and burgers at Small Cheval, or beer and nachos at Lottie’s Pub. Then take a detour up Damen Avenue. Walk the shops that line this street too or walk The 606, a former rail line turned elevated park. Keep an eye out for public art installations and murals along the way.
LOGAN SQUARE | Back on Milwaukee Avenue, end strong with all sorts of neighborhood nightlife options. Wind down on a low key note with dinner and a movie — Longman and Eagle paired with The Logan Theatre is a classic combo. Stick with the local craft beer tastings at Hopewell Brewing Company and Revolution Brewing. Or mix up your bar crawl with cocktails, dancing, distillery tours or arcade games. Between places like Billy Sunday, Estereo, Chicago Distilling Company and Emporium Logan Square — you can do it all.
Day Trip Option #2
- Neighborhoods: Old Town, Lincoln Park, Lakeview and Andersonville
- Route: Clark Street, a busy roadway that runs parallel to the lakefront
- Find: Scenic beauty and all-day entertainment
This North Side daytrip is great if you’re up for a packed itinerary of sightseeing and want to visit as many neighborhood gems as possible (beaches and a famous baseball field both warrant stops). You can travel by foot and CTA bus #22 — it’s a cheap ride and simple route to hop on and off along Clark Street as you want.
OLD TOWN | Brunch is big in Chicago and two local chains serve breakfast daily: Nookies and Kanela Breakfast Club. From there, explore nearby Old Town shops along Wells Street. Don’t be shy about sampling treats at Old Town Oil and The Spice House if you’re looking for foodie souvenirs to take home. For fun, take a look at the chocolate creations on display at The Fudge Pot or the quirky gifts at Judy Maxwell Home.
LINCOLN PARK | Make your way to the giant swath of green that is Chicago’s largest park. Beautiful Lincoln Park (side note… this is the name of both the neighborhood and the park itself) spreads out along Lake Michigan over 1,200 acres. Spend the midday hours on North Avenue Beach and soak in one of the best views of the Chicago skyline to the south. There’s also prairie gardens, public art, fishing piers and boat docks. Or opt to check out park attractions like Lincoln Park Zoo, Chicago History Museum and Peggy Notebaert Nature Museum.
LAKEVIEW | There really is no break from all the stores, restaurants and bars that string along Clark Street from Fullerton Avenue to Addison Street. For lunch, just two picks if you want to go the budget route are 5411 Empanadas and Del Seoul. Both are fast food with an international flair. If there’s a game at Wrigley Field, get inside to see the Cubs and have a Chicago-style hot dog; otherwise you can always take an official stadium tour or walk around Wrigleyville after you snap a picture of the famous marquee.
ANDERSONVILLE | Travel even further north to end the day in a neighborhood full of charm and character. Pillars of the community like Andersonville Galleria and Women & Children First bookstore embrace all things local and independent. For late-night food and drinks, Hopleaf Bar is a great hangout, but if you can make it before closing, get to George’s Ice Cream & Sweets too.
Day Trip Option #3
- Neighborhoods: Chinatown and Pilsen
- Route: 18th Street, an east-west avenue that connects the two neighborhoods
- Find: Global food, art and museums
Go on a culture trip in these two disparate enclaves separated by an industrial riverfront and major highways. 18th Street maintains a link between them. If you’re coming from downtown during the Chicago River boating season, take the Water Taxi to Chinatown to start this itinerary off right.
CHINATOWN | What used to be railroad yards is now picturesque Ping Tom Park.The draw here is a unique vantage point to take in the skyscrapers in the horizon. Follow the red ornamental walking paths that snake along the river and enjoy the landscaping and architecture that includes a pavilion, boathouse, and monuments.
Tradition calls for dim sum to begin the day, so try out the offerings at Phoenix or Dolo. Just don’t overdo it — there’s more to eat in this neighborhood. Find a mix of shops, bakeries, and restaurants in “New Chinatown” on Archer Avenue. This is Chinatown Square, a two-level outdoor mall which houses zodiac statues and a mural in its central plaza. Chinatown landmarks in the “Old Chinatown” section are clustered at the intersection of Wentworth Avenue and Cermak Road: the iconic Chinatown Gate, Nine Dragon Wall, Pavilion, and Pui Tak Center.
After sightseeing, checkmark all other Asian specialties you can eat through: Chinese barbeque, Korean fried chicken, Mongolian hot pot, Japanese ramen, Thai rolled ice cream, Taiwanese taro and tofu desserts… More than you can actually accomplish in one day but try anyway.
PILSEN | Further west on 18th Street is where Chicago’s Latino community has been a stronghold for decades. This is a changeover from the Czech settlers that preceded them, and it now welcomes residents both old and new from a diverse background. National Museum of Mexican Art is just off the main thoroughfare (19th Street) and has free admission every day. More art forms a boundary all around with continuous walls of street art (16th Street) and galleries (Halsted Street).
Casual dining at Dia De Los Tamales or Las Carnitas Uruapan will fill you up before a show. Thalia Hall is a great place for live music and the neighborhood landmark has had a long history since it went up in 1892. No need to go far for a nightcap — the massive building is also home to a restaurant, piano bar, and basement lounge. But should you want to venture out, close out your West Side tour at Lagunitas Brewing Company.