Chicago is often described as a city of neighbourhoods. By some counts there are 77 in total, each offering its own unique experience of the Windy City. But you certainly cannot visit them all in one trip. So where should you spend your time? There are seven neighbourhoods worth exploring to make your Chicago trip one to remember.

West Loop/Fulton Market

In just a few short years, Chicago's meatpacking district has flourished into dining central. Foodies of all kinds can find their next best meal in the West Loop or Fulton Market, neighbourhoods which sit sidebyside. Celebrity chefs—including Stephanie Izard, Rick Bayless and Grant Achatz—all have restaurants here. Although there is a high concentration of Michelin-starred establishments, you don't need to spend a lot to dine well. Affordable fare and tasty snacks can be found tucked in between the fine dining glitz and glam. For a worthwhile and memorable splurge, head to The Aviary for cocktails mixed by mad scientist-like bartenders. They blend unusual flavours and combinations, and their presentation will surprise you.

The Chicago River The Chicago River

Downtown/The Loop

Shopping, dining, sightseeing, and culture converge in Chicago's bustling downtown centre. From art museums and architecture to Chicago-style dogs and deep-dish pizza, you can pack in many of Chicago's must-do activities just by walking along the Magnificent Mile (depending on how fast you walk and how many stops you make along the way). In the warmer months, take a stroll along the Chicago Riverwalk; the pedestrian-only walkway presents magnificent views of the skyscrapers towering above you. From here you can also catch an architecture boat tour, which offers an interesting perspective of Chicago's tallest buildings and a crash-course in its history.

Old Town

Old Town is one of the city's oldest neighbourhoods. Make sure you visit during the day so you can see all its glorious Victorian mansions and well-preserved brick cottages. The residential community has several long-standing shops and boutiques, as well as many restaurant options. Feel like laughing? On any given night, you can catch an improv, sketch or stand-up comedy show at Second City in Old Town, where many famous comics started out.

Wrigley Stadium in Chicago Wrigley Stadium in Chicago


You don't have to be a die-hard baseball fan to enjoy one of America's oldest pastimes in one of America's oldest ballparks. Though Wrigley Field has recently been modernised, the ballpark still maintains its old-school charm and ivy-laden brick walls. In 2018, a new hotel and development with restaurants and shops opened just across the street. Wrigleyville also puts you close to the Lakeshore Trail, where you can rent bikes and take in the city's expansive Lake Michigan shoreline. Want to stick with the Wrigleyville baseball theme? Locals love the batting cages at Sluggers, which also has arcade games.


Close to Pilsen and just a few streets to the southwest, a bright red gate welcomes you to Chinatown. It is the second-largest Chinatown in the United States, but is relatively compact and easy to explore by foot. Pop into its colourful shops, order dim sum at any number of restaurants, and enjoy the sculptures, public art and murals in Chinatown Square, which also houses the Pan Asian Cultural Centre.

People dining outdoors in Chicago's Logan Square neighborhood People dining outdoors in Chicago's Logan Square neighborhood

Logan Square

Tap into your inner hipster in the Williamsburg of Chicago. All things trendy come to a head in Logan Square, where another must-try restaurant seems to open every week. Wander along Milwaukee Avenue, where you will find tastefully-decorated boutiques and well-designed restaurants. Start with a pour over coffee and finish with a pirate-themed tiki cocktail. Play vintage arcade games and shop for vinyl records along the way. Pop into bakeries and breweries in between. This is the perfect neighbourhood to spend a leisurely afternoon without an agenda.


Chicago has many ethnic communities and neighbourhoods. In the Mexican-American community of Pilsen, you will find taquerias galore and the National Museum of Mexican Art. Pilsen also has a lively arts scene, with several art galleries, lofts and event spaces condensed into a few blocks. Many open their doors to the public for an art walk on the second Friday of every month.

Getting there

Spend your time in a few of these neighbourhoods or venture out to the many others situated in Chicago—all with unique qualities and worth the visit. Book your next flight to the Windy City at or by using the convenient United app, and share your story on social media with the #MyUnitedJourney hashtag.