Wrigley Field Baseball Stadium, filled with green turf, a full crowd, and stadium lights.

8 Things To Do in Lakeview Chicago [2026]

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Looking for the best things to do in Lakeview, Chicago?  This detailed guide has got you covered!

Lakeview is one of Chicago’s North Side neighborhoods.  It’s unique because it is comprised of several smaller sub-neighborhoods like Wrigleyville, known for the Chicago Cubs. 

I have spent so much time in Lakeview with friends. Lakeview is laid-back yet upbeat. 

It is one of the most popular neighborhoods in Chicago for young adults to live in and is one of the most common places in the city for nightlife. 

I recommend exploring it, thanks to its prime location and various things to do. 

Some of the best things to do in Lakeview include Wrigley Field, Gallagher Way, 2D Cafe, Chicago’s Lakefront Trail, Laugh Factory, Southport Corridor, and two famous theaters. 

Let’s get planning!

8 Things to Do in Lakeview, Chicago

1. Wrigley Field

Wrigley Field is by far one of the best things to do in Chicago over the summer!  Nothing beats a classic Chicago Cubs baseball game.

The surrounding Wrigleyville area features tons of restaurants to celebrate post-game and walk around afterward. 

It is very crowded on game days!

2. Gallagher Way

Gallagher Way refers to the green stretch of turf directly outside of Wrigley Field.  Tons of events are hosted at this park all throughout the year.  

Visitors can enjoy weekly farmers’ markets, yoga sessions, free movie nights, and live music performances during the summer in Chicago

During the winter, Gallagher Way transforms into a festive wonderland with ice skating and holiday markets.

In October, it hosts festivals like Oktober Fest and trick-or-treating events. 

Read Next: Things to Do in Chicago in October

3. Chicago Lakefront Trail

A stretch of Chicago’s beautiful Lakefront Trail winds through Lakeview.

The portion of the Lakefront Trail through the Lakeview Neighborhood is between Fullerton Avenue and Irving Park Road.

The entire trail is 18 miles long and is extremely beautiful in all seasons, located along Lake Michigan and Chicago’s incredible skyline.

Read Next: Hiking Near Chicago

4. 2D Cafe

Two friends posing with radiant smiles in a unique, monochrome 2D Café in Chicago, the black and white striped and illustrated backdrop providing a creative twist to their girls weekend photo memories.

2D Cafe is an iconic Chicago photography spot!

The cafe features black and white comic book-style paintings from floor to ceiling.  The entire cafe has a Paris theme, and the food and drinks are a French-Vietnamese fusion.

The mochi donuts are amazing!  2D Cafe is one of my favorite Instagram spots in Chicago

5. Laugh Factory

The Laugh Factory is one of the funniest places in Chicago!  I loved my visit- I don’t remember the last time I laughed out loud (literally) for so long.

It features both renowned stand-up comedians and local talent, offering a mix that caters to various comedic tastes.

The intimate setting creates a personal experience, making each performance uniquely engaging.

Visitors praise its energetic atmosphere and diverse lineup, which keeps the audience entertained throughout the evening.

Beyond the laughs, its location surrounded by vibrant nightlife and dining options adds to its appeal.

6. Briar Street Theater

The Briar Street Theater is incredibly famous for the world-renowned Blue Man Group.

The Blue Man Group is an innovative performance that combines music, art, and comedy.

This show has been enchanting audiences since it started in 1991.

Attending a performance at the Briar Street Theater in Lakeview offers an unparalleled experience filled with vibrant visuals and a captivating soundtrack.

Book Tickets: Blue Man Group

7. Music Box Theatre

The Music Box Theatre is one of the oldest theaters in Chicago.

It is known for its classic architectural charm. The theater screens a mix of independent films, documentaries, and classic movies. 

It’s beloved in the winter for featuring Christmas classics like White Christmas and It’s a Wonderful Life.  You can even see a film on Christmas Eve in Chicago

Read Next: Best Things to Do in Winter in Chicago

8. Southport Corridor

The Southport Corridor is a vibrant and bustling shopping street in Lakeview.

It began its growth into a popular destination in the early 2000s, gradually becoming a go-to spot for both locals and visitors.

With a diverse array of boutiques, cafes, and dining options, it offers something for everyone.

Unique shops alongside familiar brands provide an eclectic shopping experience.

Seasonal events and street fairs add to the area’s lively atmosphere.

Conclusion

Lakeview in Chicago offers a popular range of activities, making it a prime neighborhood on your Chicago itinerary

This dynamic neighborhood blends cultural richness with a lively atmosphere.

Plan your Chicago trip today and experience the best that Lakeview has to offer!

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Alyssa
Alyssa

As a full time teacher who loves her job, learn how I honor my wanderlust while working a 9:00-5:00 (because I want to!) This blog welcomes all, and specifically provides resources for those seeking travel intertwined into a busy schedule (3 days to 5 weeks).