Discover Chicago‘s most vibrant neighbourhoods in this guide to the city’s diverse districts. From historic Old Town Chicago to trendy West Loop restaurants, explore the unique character and attractions that make each area special for visitors and locals alike.
Old Town: Victorian charm meets comedy gold
Most of Chicago is on a grid pattern, but in Old Town, that falls by the wayside in favour of something a touch more higgledy-piggledy. It’s also an area where handsome Victorian buildings stand out, rather than showy skyscrapers.
This is partly because the area came out relatively unscathed from the Great Chicago Fire of 1871. Whilst the rest of the city needed rebuilding, Old Town could continue what it was doing.
Comedy Central: The Second City experience
It’s now home to several traditional pubs and taverns, but the best night out comes courtesy of The Second City. This legendary comedy club gave us Tina Fey, Bill Murray and Steve Carell.
Five great things to do in Chicago
- 🏙️ Marvel at the skyscrapers – on a Chicago River architecture cruise.
- 🖼️ Take an interiors architecture tour – to see stunning glass art and mosaics.
- 🍕 Taste Chicago’s favourite dishes – on a city favourites food tour.
- 🌆 Visit the Willis Tower observation deck – and see the city from above.
- 🕵️ Discover Chicago’s gangster heritage – on a crime and mob tour.
Lincoln Park: Where green space meets urban living
Heading north from the high-rise centre, Lincoln Park is where the skyline drops. Neighbourhood bars replace the sort people come to on a big night out.
The area is dominated by the mammoth park that gives its name to the neighbourhood and runs parallel with Old Town too. The 1,200 acres of Lincoln Park stretch for 10km along the shore of Lake Michigan.
Top Lincoln Park attractions
Although most of the attractions are at the southern end, key highlights include:
- Lincoln Park Zoo – one of America’s last free admission major zoos
- The plant-filled Conservatory – a tropical oasis in the city
- Chicago History Museum – covering railroads, the Great Chicago Fire and political clashes
Wrigleyville: Baseball, bars and rainbow flags
If Lincoln Park is sedately relaxed, Wrigleyville is unashamedly rowdy. This is partly because Boystown, Chicago’s long-standing gay community hub, backs on to it and flies the rainbow flag liberally.
But it’s mainly because it’s home to Wrigley Field. This delightfully old-fashioned and idiosyncratic baseball ground is where the Chicago Cubs call home turf.
Wrigley Field: A baseball institution
Tours are available on non-game days, and tickets are surprisingly affordable if booked in advance. If you can’t get in, then Wrigleyville heaves with sports bars and classic hot dog joints.
This showcases Chicago at its most mid-western everyman.
West Loop: From meatpacking to fine dining
Up until a decade or so ago, West Loop was a thoroughly unappealing, sleeves-rolled-up industrial area. It was dominated by meatpacking warehouses.
Many of those buildings have been converted, but now serve meat rather than pack it. West Loop has undergone a restaurant boom.
Chicago’s culinary hotspot
Many of the city’s most sought-after tables are found in the neighbourhood,including:
- Girl and the Goat – pioneering restaurant with several goat-based dishes on the menu.
- Alinea – regularly billed as one of the best restaurants in the world.
You can also explore the area on a West Loop pizza tour.
Pilsen: Mexican culture and street art paradise
Pilsen may have a German-Czech name, but its vibe is very much Latin American. It’s home to the National Museum of Mexican Art, the biggest Latino arts institution in the US.
This covers 1,000 years of Mexican culture and artistic movements. But the art doesn’t just stay inside the museum.
World-Class Street Art and Culture
Pilsen is famed for its murals, many of which are of almost photographic quality. Head along 18th Street to catch some of the best, as well as plenty of bars, taco joints and artsy shops.
Thalia Hall, designed as a tribute to Prague‘s Opera House, is a fine place to catch live music.
Oak Park: Frank Lloyd Wright’s architectural legacy
Out west, safely into suburbia, Oak Park comes over as a leafy, well-to-do area. It features carefully primped lawns and sizable houses.
And it’s the latter that are of interest, as many of them were designed by Frank Lloyd Wright. The Unity Temple is the most prominent of his public buildings, but a guided tour will show you plenty of others.
Prairie School Architecture at its Finest
However, the Prairie School founder’s own home and studio offers the best example of the architectural concepts he put into practice:
- Natural materials and colours
- Horizontal lines and overhanging eaves
- Rooms flowing into one another
- Integration with the surrounding landscape
The Frank Lloyd Wright Trust runs tours of the home and area.
More Chicago travel
Other Chicago travel articles on Planet Whitley include:
- Touring Chicago’s gangster heritage.
- Why you should do a Chicago architecture walking tour as well as a cruise.
- Do I need to buy Art Institute of Chicago tickets in advance?
- The Tiffany dome in Preston Bradley Hall: Chicago’s most underrated attraction?
- The best attractions in Chicago’s Millennium Park.
