I’ve lived in cities as large as London and as small as Asheville, North Carolina (the latter of which packs a punch of flavor that hits harder than many major cities twice its size). Suffice it to say, I would have never anticipated landing in a tiny college town in the cornfields, but I’m only an hour from the Second City, and Chicago enthralls me every time I hop on the Metra and ride into the city.
This guide to Chicago contains 10 stops that you might not have already thought about, with destinations both in the city and within a 45 minute Metra ride, for those of you who are bold enough to hop on a train. I know you will likely go to the Bean and the Shedd Aquarium or check out a game at Wrigley Field. But many of the locations in this guide are very close to typical tourist spots like these, so you can also add them to a “by the book” Chicago vacation.
A fun guide to Chicago shopping spots
Milk Handmade
Andersonville
If you’re looking for sustainable, handmade fashion, be sure to check out Milk Handmade in Andersonville, otherwise known as the “Buy Local” capital of Chicago. Its clothing offerings include a variety of options from local designers, and it also offers apparel from its in-house brand, Milk Private Label. Milk carries accessories as well, and its apothecary features soaps, candles and perfumes from local brands.
Milk Handmade works exclusively with independent designers, which ensures that you’ll leave with a unique product that shows you’re in the know. Check out its sister bridal shop, Honey Bridal, for handmade, slow fashion wedding gowns.
The Silver Room
Hyde Park
An intentionally curated space for global fashion with a focus on African American jewelry, The Silver Room also hosts art shows and music parties. Its mission is to create a global community through art and culture. The store often hosts pop-ups with Black-owned brands to keep its collection fresh and eclectic.
Before you go, check out what events are happening on the venue’s Linktree. You might be able to catch a poetry reading or another cultural event.
Great places to eat in Chicago
Proxi Chicago
West Loop
If you’re looking for a combination of global street food and sexy cocktails, as well as a comfy front lounge to linger in, head to Proxi. The Michelin Guide Restaurant offers a chef’s menu with shareable starters and individual entrees, and it also has a nonalcoholic cocktail list that is as glamorous as its full-proof options.
I tried the Python Boot, a mocktail that contains papaya, ginger, cilantro stem and salt. It had a spicy bite, and I liked it so much that I ordered a second. The tempura elotes were the perfect starter, and the Thai yellow curry with bass, shrimp and mussels rounded out dinner.
All Chocolate Kitchen
Geneva, IL
We’re going to send you out of the city for this one, but we promise it’s worth it. Hop on the Metra from Ogilvie and take the Union Pacific West to Geneva, Illinois, to taste some goodies dreamed up by celebrity chef Alain Roby at the All Chocolate Kitchen. When my partner and I went, we had dessert first and later marveled at the intricate details on the sugar sculptures, which include an iguana, an astronaut and a castle with little edible bricks. We also tried the chocolate gelato, and I’ve heard great things about their truffles and baked goods as well.
Geneva is worth visiting for a full day trip, as it boasts a variety of shopping options and enough restaurants for a roundup of its own. The Fabyan Japanese Garden near the river is a nice spot for a walk. There are lots of enticing options nearby (The Burger Social is great), but if you can go ten minutes out of your way, check out Sword Fish Sushi in Batavia as well.
Chicago entertainment you can’t miss
The Salt Shed
Salt District
Located in the former Morton Salt factory, the Salt Shed hosts a variety of music events, both indoors and outdoors. Their acts have included the Flaming Lips and Death Cab for Cutie. The venue was constructed to preserve the building’s architectural integrity, which is a Chicago icon in itself.
One word of advice: Find out what the food situation is in advance. Although the venue often hosts food trucks and is connected to the new Goose Island Pub, it can be busy. When I went for an indoor show, the on-site food options were sparse, and the restaurants within walking distance were booked solid.
Kit Kat Lounge and Supper Club
Northalsted (aka Boystown)
You can’t write a guide to Chicago without mentioning a fun visit to Boystown. The Kit Kat Lounge and Supper Club is a twofer because it has excellent food and hosts drag shows every night—as well as a Sunday drag brunch. The venue is home to the iconic Kit Kat Divas and has a menu with standard fare that includes many vegan, vegetarian and gluten-free options.
Walking around the neighborhood is also an entertaining experience, and if you like to shop secondhand, there are some excellent charity shops nearby. I found some shockingly cheap designer handbags at Out of the Closet Thrift Store.
Chicago art and design to appreciate
The South Side Community Art Center
Bronzeville
The oldest African American art center in the United States, the South Side Community Art Center, is located right in Bronzeville—a neighborhood with a rich history of being an African American cultural center and the home of Ida B. Wells, Louis Armstrong and Richard Wright, among other notable and influential Black figures.
The art center boasts an enviable permanent collection and hosts exhibitions as well. If you have kids in tow, you can take them to the Bronzeville Children’s Museum afterward as a prize for patiently looking at art with you.
The Merchandise Mart
Downtown
The Merchandise Mart, or THE MART, is the world’s largest commercial building and design center and was the largest building in the world when it was built in 1930. If you’re into architecture and interior design, the 4.2 million square foot, 25-story art deco building is a great place to get lost in with its commercial and residential design showrooms.
Stop by at night to see Art on THE MART, one of the largest permanent digital art projections in the world. Its lineup of artists rotates annually. It’s a very quick walk from the Theatre District, so if you have tickets to one of the many Broadway shows that visit Chicago, you can pop over to THE MART beforehand to visit the showrooms or afterward to view the art installation.
Good hotels in Chicago
Acme Hotel
River North
If you’re looking for a boutique hotel with a counterculture vibe, the Acme Hotel is an ideal place to stay. According to its website, the hotel has partnerships with local music venues, and it also features on-site art exhibits, including a mural, graffiti art in the stairwells and an outdoor installation of painted mannequins. Acme also has a hotel bar with a craft cocktail menu and a variety of antique whiskeys. The famous Pizzeria Uno is steps away as well, so you can easily get your Chicago deep dish pizza fix.
Have a private party planned? Inside the Acme Hotel is the Bunny Slope, an intimate bar with a hot tub that is only available for private parties of up to 20 people.
Hotel Versey
Lincoln Park
Don’t want to stay in the Loop? Neither do I, most of the time. Hotel Versey is situated in Lincoln Park and is only a 21-minute walk from Boystown and a 32-minute walk from Wrigleyville. The hotel is located in a fun commercial neighborhood with a variety of places to eat and unpretentious retail options. For a laid-back, inexpensive lunch, stop by 5411 Empanadas, which is a two- to three-minute walk away. There are many other places to eat as well, with a variety of cuisines. And if you’re in town for a concert, The Vic Theatre is about a 15-minute walk from the hotel.
The hotel was recently acquired by NexGen Hotels, so some things about it may change, but its iconic status as a destination for rock bands (the hotel boasts that it has hosted Radiohead, Alanis Morrisette and Nirvana, among other A-list bands) and tight operations were part of what attracted the hotel management company to the deal. Hopefully this means that NexGen will leave Hotel Versey’s artsy aesthetic intact.
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