10 Bucket List Things to See and Do in the West Loop

It’s time to take another look at West Loop.

This vibrant Chicago neighborhood has undergone many changes throughout the city’s history. Originally serving as a center for manufacturing in the 1800s, the West Loop has grown to be one of the trendiest areas in Chicagoland, full of restaurants, shops, and plenty of unique things to see and do.

The West Loop is a neighborhood with something new to experience around every corner. Ready to start exploring this bustling area? Here are ten West Loop gems to put on your bucket list:

1.) Browse the Randolph Street Market

Home to hundreds of unique vendors, the Randolph Street Market is a sprawling, indoor-outdoor festival that runs every month. Full of one-of-a-kind clothing, accessories, home goods, and art, the Randolph Street Market is sure to have something that catches your eye, whether your style is classical, quirky, or more cutting edge. Even if you’re not looking to buy, the Market is a vibrant place to wander around, grab a bite to eat, and enjoy the sights and sounds of Chicagoland.

For more information on dates and admissions, check out Randolph Street Market’s official site, here.

2.) Marvel at Mary Bartelme Park

Mary Bartelme Park is an oasis of green space in the bustling West Loop, with a quirky character all its own. For starters, Bartelme Park welcomes visitors with its iconic stainless steel gates – a popular spot for a perfect Chicago Instagram moment. Inside the park, you can take your dog to play in the sunken play area, complete with ramps, ledges, and a giant dog bowl. Or, lounge around on the viewing hill to soak in an unparalleled view of the Chicago skyline.

For more on Mary Bartelme Park, visit its Chicago Park District site, available here.

3.) Explore the Chicago French Market

Want the feeling of being whisked away to Europe – without having to book a flight out of Chicagoland? If a Paris getaway sounds like the thing for you, then the Chicago French Market should be on your West Loop “to-do” list. This charming indoor market is open year round, and hosts a a variety of different vendors selling fresh ingredients to cook at home, or prepared foods ready to enjoy for breakfast, lunch, or dinner.

To learn more about the Chicago French Market, take a look at its official website, here.

4.) Discover Something New at City Winery

Whether your passion is wine, art, music, or food – or some combination of all of the above – you’ll find something to enjoy at City Winery. In addition to serving as a world class bar and restaurant, City Winery also hosts musical performances from national touring acts, as well as Chicagoland locals about to make it big. Local artisans also produce their own wine on-site, making City Winery a great place to visit whether you’re looking to tour a winemaking facility, taste test some new vino, or even help create a wine of your very own.

For more on all that City Winery has to offer, visit their official website, here.

5.) Indulge in Decadent Desserts at BomboBar

Nestled on a side street next to Bar Siena, BomboBar has earned a glowing reputation for its breathtakingly extravagant sweets, including towering scoops of gelato and decadent milkshakes. Whatever you order, be sure to top it off with this spot’s signature treat, the bomboloni, a hole-less dougnut that diners can inject full of chocolate, fruit, caramel, or any number of other fillings.

With BomboBar, you’ve got to see it to believe it. Check out pictures and get a look at the menu on this sweet spot’s website, here.

6.) Find a New Favorite Artist at a West Loop Gallery

The West Loop area is home to some of Chicagoland’s top art galleries and displays. An afternoon in a West Loop gallery might be all that it takes to discover your next favorite artist or exhibition.

Fortunately, there is no shortage of options! When you’re looking for the best that the Chicagoland art scene has to offer, consider popping into the Mars Gallery, which hosts the works of pop artist Peter Mars, as well as exhibits and events showcasing other art world luminaries. For displays of cutting edge modern art from many disciplines, you may also want to pay a visit to Kavi Gupta, the Carrie Secrist Gallery, or the Andrew Rafacz Gallery.

7.) Eat Your Way Down “Restaurant Row”

Cutting through the heart of the West Loop’s old industrial area is Randolph Street. Once the home to the core of Chicago’s produce and meatpacking industries, today this strip is known for its bevy of world-renowned restaurants, which locals lovingly call “Restaurant Row.”

Whatever you have a taste for, there’s bound to be a spot on this world-famous road that will satisfy. From the upscale diner classics at Au Cheval, to Iron Chef Stephanie Izard’s thoughtful fare at Girl & the Goat, to the mouth-watering Mexican cuisine of Cruz Blanca and Leña Brava.

8.) Glimpse Chicago History at Union Station

Every day, countless commuters make their way through Chicago’s Union Station, zooming in and out on a Metra or Amtrak train. While it is still an active transportation hub, Union Station is also a window into Chicago’s legendary past. First envisioned by architect Daniel Burnham in his 1909 Plan of Chicago, Union Station is a monument to the city, and is home to some of the most impressive architecture you’ll see anywhere in the country. To get an insider’s look, consider signing up for a tour with the Chicago Architecture Center or Chicago History Museum.

Want to get a feel for Union Station before you visit? You can find photos, facts, tickets, and more on the station’s website, here.

9.) Sneak Into a Speakeasy In One of the West Loop’s “Secret” Spots

For many people, talking about Chicagoland history instantly calls up thoughts of the Prohibition era, when secret bars and restaurants popped up in spots all around the area. Today, there are plenty of watering holes around Chicagoland keeping the feeling of the speakeasy alive, including a few spots in the West Loop.

Two spots putting a distinctly modern twist on this 20s-era trend are Booze Box and Blind Barber. With a secret entrance in an alleyway next to Sushi Dokku, Booze Box is sleek and secluded, serving up drinks and tasty Japanese snacks in an underground setting. Blind Barber, meanwhile, is a fully functioning barbershop – which just happens to have a backroom that opens up into a funky lounge after the sun goes down.

10.) Update Your Wardrobe at a West Loop Clothier or Boutique

Whether you’re looking for an outfit for your next night out, a funky piece of jewelry, or accessories you won’t find anywhere else, the West Loop has plenty of clothing shops ready to deck you out in style. For those looking for a sharp, expertly-tailored suit, BLVDier offers custom suits and shirts. Or there’s Live Grit, a one-stop shop for fitness nuts looking for clothes made for running, swimming, or biking. For fashionable flair, find time to poke around Tribeca Boutique or Soñador Boutique.

Have any more questions about the West Loop? Be sure to take a look at our neighborhood guide video, available right here.

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