10 Bucket List Things to Do in Uptown and Andersonville

Uptown is one of the most unique and interesting spots in Chicagoland. This large area — which includes Buena Park, Sheridan Park, and much of Andersonville — is home to countless restaurants, great shopping, and some of the most eclectic architecture you’ll find in the city.

Planning to pay a visit to Uptown and Andersonville? There are enough things to see, do, and experience to last you a lifetime. Here are 10 bucket list destinations you can’t miss:

1.) Slurp Noodles on Argyle Street

Fans of serious cooking know that one of the best stretches in all of Chicagoland is just off of the Argyle Red Line L stop. Also known as “Asia on Argyle,” this area is a well-known destination for foodies to grab a steaming hot bowl of pho, pick up a quick banh mi sandwich, or settle down for some authentic Chinese barbecue. No visit to Argyle Street would be complete without sampling the dishes from Tank Noodle, Sun Wah BBQ, or Pho 777, among other unique local gems.

2.) Groove to Live Jazz at the Historic Green Mill

The music and the cocktails flow from sundown until the early morning at this world-famous Uptown spot. Step into the Green Mill and you’re instantly whisked back to the Chicago of the 1930s and ‘40s, all deep booths, white tablecloths, and bright neon signs. During a break between sets, ask your server about the Green Mill’s history; you’re sure to hear a story or two that you’ll remember forever. When the jazz isn’t jumping, the Green Mill is a popular gathering place for artists and comedians, who pop in to perform at the Paper Machete revue or the Uptown Poetry Slam.

For more on the Green Mill, including FAQs and a performance calendar, you can visit the bar’s official site, here.

3.) See Your Favorite Band at the Aragon Ballroom or Riviera Theatre

Hop off the L train at the Lawrence stop, and you’ll be in walking distance to two of the best live music venues in all of Chicagoland. Just to the north, on Lawrence Avenue, you’ll find the Aragon Ballroom, an ornate Mediterranean-style performance hall hosting concerts from some of the biggest touring acts in the country. And just south, at Racine and Broadway, you’ll find the Riviera Theatre, which welcomes concertgoers inside under an iconic, glittering marquee.

4.) Discover Retro Finds at the Vintage Garage

When you start brainstorming the best places to shop for mid-century modern furniture, antique collectibles, or far-out retro fashions, the words “parking garage” may not end up high on your list. But for much of the year, the very best place to go for antiques and all things vintage is the parking garage located at 5051 N. Broadway. On certain weekends, this space transforms into an open air market, where buyers can wander through the wares of some of the biggest collectors and re-sellers in Chicagoland.

The Garage will be on hiatus for much of 2019 due to construction, but you can find pop-up events and more information on the market’s official site, available here.

5.) Be Amazed at the Chicago Magic Lounge

You enter a laundromat and walk up to a washing machine. But this isn’t an ordinary washer. It’s a door. And behind this door, you’ll find the Chicago Magic Lounge, one of the most mysterious destinations in Chicagoland. Home to two theater spaces, a performance bar area, and some of the best magicians you’ll find anywhere in the country, the Magic Lounge is a great place to enjoy an evening of amazement and wonder. Whether you want to see someone disappear on a grand stage or puzzle over card tricks and sleight-of-hand magic up close, this hidden gem is the spot for you.

To see what’s playing or learn more about the venue, you can visit the Chicago Magic Lounge’s official site here.

6.) Take a Dip at Montrose Beach

Offering stunning views of the Chicago skyline and a designated spot to splash around with your furry friends, Montrose Beach is one of the most popular places to take a dive into Lake Michigan, or simply lay back on the sand and soak in the sun. The beach has a designated dog area that’s a perfect spot to take your puppy to play in the surf. Montrose Beach is also a great launching point for kayaks, and there’s a stunning natural area, including a bird sanctuary, just a short stroll away from the beach.

To learn more about all of the amenities of Montrose Beach, you can visit its official Chicago Park District page, here.

7.) Taste Your New Favorite Beer at Hopleaf

Chicagoland is home to plenty of places to get a beer and a bite to eat. But Hopleaf, an Andersonville staple, isn’t your ordinary beer bar. Since 1992, Hopleaf has been serving up a diverse array of craft brews, making it a famous gathering spot for serious beer fans and locals looking for a fun night out. The bar routinely hosts events highlighting certain styles of beer or local breweries, and the kitchen serves up a rich and filling menu that changes with the seasons, all designed to pair perfectly with your favorite pint.

To learn more about the history of this beloved neighborhood joint, you can visit Hopleaf’s official site, here.

8.) Take a Stroll Through the Andersonville Galleria

Nestled in the heart of Andersonville’s bustling retail corridor, the Andersonville Galleria is a unique, multi-level space home to more than 100 vendors. Pay a visit to this sprawling marketplace, and you’ll come across everything from home goods, to jewelry, to food, to clothing, to one-of-a-kind artwork, all presented by a local artisan or vendor with a story to share.

To take a digital tour of the Galleria or see what vendors have set up shop, you can visit the market’s official site, or check out its Facebook page for updates.

9.) Experience Live Theater, the Neo-Futurists’ Way

The Neo-Futurists have been bringing funny, shocking, sad, absurd, and thought-provoking theater to Chicagoland audiences for more than 20 years. Today, visitors flock to their permanent theater, sometimes known as the Neo-Futurarium, for an ever-changing list of performances. This includes the company’s signature weekend show, Infinite Wrench, which the group describes as “a barrage of two-minute plays for a live audience.”

To learn more about the philosophy of the Neo-Futurists or plan your visit, you can check out the group’s official site, here.

10.) Discover Art and Culture at the Haitian American Museum of Chicago

Founded in 2012, the Haitian American Museum of Chicago is an institution dedicated to showcasing works from emerging global artists, while serving as an event space and meeting room for cultural groups and performers from across the city. Spend your day at HAMOC browsing the ever-changing exhibitions on display, picking a book up from its donation-driven library, joining in a community dialogue, or catching a special film screening.

To learn more about the Haitian American Museum of Chicago, its official web page is available here.

Want to Explore Uptown and Andersonville Even Further?

To discover even more about the unique neighborhoods that make up Uptown and Andersonville, please visit our official guide to the area’s real estate market, available here. 

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