Are you looking for unique things to do in Chicago? This list is full of Chicago hidden gems, small businesses, independent designers, music venue rebels, and dives that are some of the best places to visit in Chicago!
Looking for unique Mexican food in Chicago? Head to Birrieria Zaragoza in Archer Heights! This Chicago restaurant might seem small due to its tucked-away feel and limited seating, but locals will assure you it packs a big punch! This hidden treasure has been honored with claims of “best tacos around,” and it’s no wonder why. All of the dishes feature tender, juicy birria (goat meat). In other words, it’s not the same-old ground beef or shredded chicken. And good news for travelers—Birrieria Zaragoza is just a hop, skip, and a jump from Midway Airport!
The Book Cellar
Located in the heart of Lincoln Square, The Book Cellar is one of the best bookstores in Chicago. With a great selection, a cozy cafe, and plenty of places to sit down with a cup of coffee, a beer, or a glass of wine, The Book Cellar is an escape for many Lincoln Square neighborhood residents. The Chicago bookstore also hosts local author readings and can provide excellent recommendations based on your reading preferences!
Cafe Jumping Bean
With reliable coffee, fresh bakery items, and delicious specialty sandwiches like molletes, Cafe Jumping Bean in Pilsen is one of the Chicago coffee shops you must visit! It’s a quaint spot with an inviting atmosphere, friendly staff, and brightly-colored walls that will pull you out of your morning funk. That’s why the University of Illinois Chicago students and Lower West Side, Chicago residents keep coming back for more. Pop in for a quick Iced Mocha and muffin, or hang out for a while with a cappuccino to people-watch.
Getting to Calumet Fisheries in South Chicago is a hike for many Chicagoans, but this little smokehouse shack next to the Calumet River is a Chicago seafood lover’s paradise! Family-owned and operated since 1948, it’s known for having the best fried fish in Chicago. Take your pick from Fried Shrimp, Smoked Salmon, Fried Catfish, Oysters, and so much more—you won’t be disappointed! Calumet Fisheries is cash only, doesn’t have bathrooms, and only has a few picnic tables outside (It’s mostly a carryout or eat-in-your-car kind of place). But don’t let that deter you from going! It’s more than worth it for some of the best seafood in Chicago.
Challengers Comics + Conversations
Challengers Comics + Conversations in Bucktown isn’t one of your typical comic shops in Chicago. This comic book store is well-organized from A to Z with clear markers so you can find that Dark Horse comic or Manga you’re looking for without trouble. More importantly, the staff doesn’t just stand behind a counter waiting for you to check out. They’re the “Conversations” aspect of the store’s name. These knowledgeable and attentive people will not only help you find the comic you need (or even something new), but they’ll be there to strike up conversations about comics.
Chicago’s Home of Chicken & Waffles
Soul food takes root in Chicago in the form of Chicago’s Home of Chicken & Waffles. This restaurant is best known for its namesake dish—perfectly seasoned fried chicken paired with a warm, golden waffle and maple syrup. But that’s not the only good cookin’ you’ll find at one of the best restaurants in Chicago! You can also get Grits, Southern Fried Catfish, Sweet Potato Pie, Mac & Cheese, Red Beans and Rice, and much more! The best part? You can get breakfast, lunch, and dinner all day at Chicago’s Home of Chicken & Waffles—and if you go to the Oak Park location, you can BYOB from 5 p.m. to 9 p.m. (with a $10 corking fee).
For some of the best donuts in Chicago, you need to check out Dat Donut in Chatham! This little mom-and-pop shop has been around since 1994 and serves Chicago donuts that are “too good to dunk.” Owners Darryl and Andrea are dedicated to serving the best donuts in town with friendly service—and if you ask anyone in the neighborhood, they’ll tell you Dat Donut delivers on both fronts. You have to try the famous Big DAT, a donut so big that it makes your hands look small!
The Driehaus Museum
Take a trip back to America’s Gilded Age (1870s to early 1900s) with The Driehaus Museum. This is a Chicago attraction you can’t miss, just off the Magnificent Mile was the home of banker Samuel Mayo Nickerson and was later turned into a museum in 2003 by philanthropist Richard H. Driehaus, who preserved and refurbished the home. For $20 (adult pricing), you can explore the entirety of The Driehaus Museum and examine intricate details, such as The Gallery’s stained glass dome and the Main Hall’s 17 different types of marble. This museum isn’t just an architect’s dream—it’s a view into the history of Chicago.
Fat Johnnie’s Red Hots
North Side hot dogs have nothing on South Side, especially if those hot dogs come from Fat Johnnie’s Red Hots! Fat Johnnie’s serves up high-quality “eat on the sidewalk” dogs for cheap. And they have a slightly different take on the traditional Chicago dog: a cucumber instead of a pickle. It might not seem like that big of a difference, but locals will tell you this messy, chili-covered dog is one of the best they’ve ever had. Fat Johnnie’s little roadside shack might not be much to look at, but who cares when the Chicago hot dogs are this good? Be sure to bring cash if you visit!
Want to kick back with a beer and a delicious meal? G&O has you covered. Just off Grand and Ogden avenues (which give G&O its name), this Chicago gastropub features local beers, craft cocktails, wine, and in-house liquor infusions. The bar also has an excellent patio that can seat around 30 to 40 people, so it’s a great spot for sunny days and cool nights. And you can’t forget the food! The Mac & Cheese, Pomme Frites, and Crab Fondue make for excellent starters while the Burger and the Steak will fill you up for dinner. G&O also serves brunch on Saturdays and Sundays from 10:30 a.m. to 3:30 p.m.
Go 4 Food
Looking for Chinatown Chicago restaurants? Check out Go 4 Food! This Chinese fusion restaurant on 23rd Street serves lunch and dinner and offers dine-in, takeout, and delivery. Locals recommend you go bold with your meal choices when you visit Go 4 Food rather than stick to the “traditional” dishes you can find at other Chinese restaurants in Chicago. Try the Sweet and Sour Chinese Style Ribs, the succulent Walnut Shrimp, or the spicy Chili Fusion Dungeness Crab with some Millionaire Style Fried Rice. You won’t be disappointed at one of the best Chinatown restaurants in Chicago!
Green Mill Cocktail Lounge
Uptown Chicago is home to Green Mill Cocktail Lounge, one of the best bars in Chicago! Originally called Pop Morse’s Roadhouse, the lounge opened in 1907 and was later renamed Green Mill Gardens. It was a hangout of Al Capone (His favorite booth is still there to this day) and hosted jazz musicians like Franz Jackson and Von Freeman. Today, Chicago jazz still influences the ambiance of the Green Mill. In fact, there’s an unspoken rule that you don’t talk when performers are on stage at this Chicago jazz club. It’s the kind of dark, smokey place with music and cocktails that will transport you back to the days of yore.
Gullivers Pizza & Pub
Everybody’s got their favorite pizza joint. Giordano’s, Lou Malnati’s, Gino’s East, Pequod’s Pizza. The list goes on and on. But if you’re looking for a new place to get Chicago-style pizza, check out Gullivers Pizza & Pub in West Ridge! Home to the “pizza in the pan,” this spot for Chicago pizza has been around since 1965 and has some of the best deep dish pizza in Chicago. They’ve been using the same recipe since opening and bake every pie in a brick oven to ensure the crust is cooked to perfection. You can get pizzas from 9″ up to 16″, as well as pasta, ribs, fajitas, and more. Gullivers Pizza also has a great outdoor patio if you want to sit outside. And they deliver deep-dish pizza in Chicago!
The Hideout in Chicago is a hidden treasure with the most literal name. It is, in fact, a hideout for those seeking creative freedom and artistic rebellion—and has been since 1934! This Chicago dive bar hosts musicians and bands known for their alternative styles, whether that’s country, punk rock, or indie. Tucked back in an industrial area between Noble Square and West Town, The Hideout is one of those Chicago bars that looks sketchy from the outside (or like it could be somebody’s house). But the drinks are good, the bartenders are fast, and the bar frequently hosts events to support the local community. What’s not to love?
With retro furnishings, low lighting, and a great stage, Hungry Brain in Roscoe Village has a chill, vintage vibe that meshes well with its intimate live music and spoken word performances. The bar has a good selection of canned and bottled beer, and the cocktails are known for being extra strong. Though the venue shut down for a brief period and re-opened with new ownership, it hasn’t lost its original charm. It’s still a BYOF establishment (meaning you can bring in whatever food you want), and it’s still a haven from mainstream entertainment. Be sure to stop by this Chicago neighborhood gem on Sundays for live jazz!
La Casa de Samuel
With a building designed to resemble rustic Mexican architecture, La Casa de Samuel in Little Village feels authentic. It’s family-owned and operated, features handmade tortillas and exotic Mexican dishes, and even has live music on Sundays. A lot of first-timers mistake the service for being slow, but locals will tell you that’s just because La Casa de Samuel is all about providing a relaxing experience with good Chicago food and a comfortable atmosphere. So kick back with a Michelada and truly savor your food! Not sure what to get? La Salsa de Molcajete, Cabrito Estilo Monterrey, and Cordonizes en Salsa Verde come highly recommended!
Eclectic and adorable gifts made by local Chicago artists are what you’ll find at Komoda. Owner Sherri Gregorczyk tries to curate the most unique knick-knacks for women, men, and children, and it’s what makes Komoda a favorite among small Chicago boutiques! Whether you’re looking for something for yourself or something for someone else, you’ll find the perfect item here. Jewelry, household décor, soaps and lotions, coffee table books, toys, scarves—whatever you need, Sherri can help you find it!
Community is at the heart of Kusanya Cafe in Englewood. Even its name means “to gather, collect, accumulate” in Swahili. This Chicago cafe strives to be a place of empowerment and encouragement for local residents, whether that’s creating somewhere people can go to meet their neighbors for Chicago coffee or playing host to an evening poetry reading for community youth. Of course, the food also draws locals to Kusanya Cafe. Give the Chance the Veggie Wrap a try. Or go for the Funkadelic Chicken Sandwich. Regardless of what you order, don’t sit there by yourself. Get to know the people around you!
Music Box Theatre
Music Box Theatre in Wrigleyville has an old-timey cinema feel with its creaky but comfortable seats, its stage in front of the screen, and an Art Nouveau-style interior. And while everything in the world of film and movie theaters has changed dramatically since its opening in 1929, Music Box Theatre still keeps the glamour of “going to the movies” alive. It helps that it’s one of the few movie theaters in Chicago that uses real butter on popcorn! You can catch everything from foreign films and documentaries to Oscar-nominated movies and cult classics like The Rocky Horror Picture Show. Also, be sure to join the theater for its annual Christmas Sing-A-Long & Double Feature!
Searching for a good Creole restaurant in Chicago? Norman’s Bistro in Kenwood is exactly what you’re looking for! This modern take on American Creole with a Brazilian flair means not only amazing food but also an innovative menu with high-quality ingredients and just enough spice to keep you coming back for more. Try the tender St. Louis Spare Ribs, succulent Caribbean Flame Grilled Lamb, or soulful Shrimp, Chicken, and Lobster Gumbo! And don’t forget to stop by for live jazz on Sunday nights at one of the best Chicago restaurants!
In the back of a Wabash Avenue jewelry mall in The Loop, you’ll find one of the best spots in Chicago! Mediterranean restaurant Oasis Cafe is the go-to for Chicagoans who need fast, cheap lunches. Shawarma, Falafel, Hummus and Pita, Cucumber Salad, Shish Kebab, Lentil Soup—all of your favorite Chicago Mediterranean food picks are here, and you can eat them at Oasis Cafe or carry them out! While the restaurant itself might not be much to look at, the staff is super friendly, and the food is outstanding. This may very well become your new lunch spot in The Loop!
Just a short walk from the Magnificent Mile, you’ll find one of the quaint Chicago shops called P.O.S.H. in River North. Since 1997, this little home décor shop has been providing Chicagoans with unique, authentic, and vintage pieces they won’t find anywhere else! There’s an ever-changing mix of European flea market finds at P.O.S.H. with everything from china and silver to jewelry and seasonal decorations. Every item has a story and a personality, too, and that’s what owners Karl Sorensen and Stephen Weigel love about their finds! Perhaps it was a tea set used in the English countryside or dinnerware used by a famous hotel. Like the items they sell, this Chicago boutique is one-of-a-kind!
Trying to find that Mid-Century Modern buffet you’ve always wanted in your kitchen? Or perhaps an antique mirror for your entryway? Or maybe a funky armchair for your reading nook? Praha in Roscoe Village is the Chicago hot spot to visit! This antique store in Chicago has a new selection of interesting pieces in store every week, and the prices are fairly affordable compared to most furniture shops, the latter of which is a huge bonus for thrifters! If you need a suggestion or help finding a specific style of furniture, don’t hesitate to ask owners Todd Nyenhuis and David Foster, who are always around.
Are you looking for a Chicago business where you can get unique gifts at an affordable price? Stop by ShopColumbia in South Loop! This Chicago small business features artwork, prints, stationery, photography, jewelry, clothing and accessories, knick-knacks, and much more. And all of the items are created by the students at Columbia College! It’s a great way to support young artists.
Skylark in Pilsen is one of those Chicago dive bars that might look rough on the outside, but on the inside, it’s friendly and totally chill. With a killer jukebox, laid-back service, and an ambiance that somehow feels as comfortable as your living room, Skylark could very well become your new favorite hangout. Did we mention that the Chicago craft beer selection is excellent? And we can’t forget the amazing food, like Mac & Cheese, Tater Tots, and Burgers!
SPiN in River North is one of the best Chicago bars. Sure, it has flat-screen TVs so you can catch your favorite games, and there are plenty of beer, liquor, and cocktail options. But what separates SPiN from other clubs in Chicago is that it’s dedicated to ping-pong. As in, you can reserve a table ($39/hour) and play with friends! Paddles and balls are included, and you get enough balls that you don’t need to chase after them. You also get table-side drink service while you’re playing so you don’t have to postpone the game every time someone needs a drink. Be sure to check out SPiN’s special events for DJ showcases, ping-pong pro matchups, and unlimited play nights!
Stanley’s in Back of the Yards is a Chicago classic! This restaurant and bar was established in 1924 and moved around a few times before finally settling down at its 4258 S. Ashland Ave. location, where it’s been since 1935. This local spot serves up some of the best food in Chicago with old-fashioned lunches like Meatloaf and Turkey Dinners with corn, mashed potatoes, and mixed vegetables—that are a hit with the working crowd during the day. At night, Stanley’s becomes one of the most fun places in Chicago with a Cheers-like neighborhood hangout where the drinks are cheap and the staff knows your name.
If quirky shirts and funny gifts are your thing, then Strange Cargo in Lakeview, Chicago is going to be your new favorite place for unique Chicago shopping. Find throwback Chicago sports jerseys, pop-culture prints, and more in adult sizes all the way down to infant sizes! Not to mention, if you’re looking for high-quality, custom-printed t-shirts for a group or an event, Strange Cargo can help you out! The awesome staff behind Strange Cargo will make sure you don’t go home disappointed!
Streeter’s Tavern in Near North Side, just down the street from the intersection of Chicago Avenue and Michigan Avenue, is the perfect place to stop after a long day of exploring the Magnificent Mile. This Chicago dive bar has an excellent outdoor patio, a great selection of craft beers on tap, indoor games like pool and giant Jenga, and a menu full of greasy bar favorites like burgers, wings, and rings (from neighboring Downtown Dogs)! As for clientele, it’s a unique mix of college students, downtown execs, and blue-collar workers. The drinks are cheap and the servers are extremely friendly, which is why locals love coming to Streeter’s.
Locally-designed, handcrafted clothing and accessories are what you’ll find at Squasht Boutique in Ukrainian Village. Lesley Timpe, the independent designer and owner of Squasht Boutique, offers a great variety to her clientele with each seasonal collection from her in-house brand, as well as the collections from other Chicago designers. From vintage-modern dresses and handmade hats to sophisticated European-influenced tops and bottoms, it’s easy to find something that fits your personal style. Most of the items in the shop are under $150 as well, which is a good bargain for Chicago shoppers on a budget!
Tufano’s Vernon Park Tap
Want good Italian food in Chicago? Head to Tufano’s Vernon Park Tap in Little Italy! This mom-and-pop restaurant has been passed down through the Tufano family since its opening in 1930 and is one of the best Italian restaurants in Chicago. But even though faces may have changed throughout the years, the dedication to making Italian cuisine the whole family can enjoy has been a constant. Locals love the Sinatra-like ambiance of the joint, and they highly recommend the fried calamari. Of course, you can’t go wrong with any of the traditional pasta dishes. Just be sure you pair it with a glass or bottle of Chianti! (Note: this is a cash-only establishment.)
Windy City Hot Dogs
“I just keep coming back” is how every South Side local talks about Windy City Hot Dogs in West Lawn. This family-owned restaurant just down the street from Midway Airport is keeping the tradition of good food and good service alive. It might be a cash-only joint with limited seating, but the menu is enormous, the prices are cheap, and the food is to die for! Don’t be fooled by the name—Windy City Hot Dogs doesn’t just serve Chicago-style hot dogs. You can also get Italian sandwiches, cheeseburgers, and gyros! And don’t forget about the “secret menu” (which is, more or less, whatever you can dream up using what Windy City Hot Dogs has among its ingredients).
Wolfbait & B-girls
Looking for an independent boutique that supports local Chicago artisans? Pop by Wolfbait & B-girls in Logan Square! Owned and operated by Shirley Kienitz and Jenny Stadler—who also create their own collections in-house—Wolfbait & B-girls is all about showcasing the work of more than 170 local designers and Chicago businesses. Find beautifully handcrafted jewelry, candles, vegan soaps, artwork, clothing, and Windy City memorabilia all in one place! If you love buying local, or if you’re looking to purchase a unique gift from a small business in Chicago, this hidden gem is one of the best places to go in Chicago.
Woolly Mammoth Antiques, Oddities, & Resale
You won’t find another Chicago vintage store as unique as Woolly Mammoth Antiques, Oddities, & Resale. This antique store in Andersonville has a little bit of everything—vintage furniture, eclectic artwork, wacky books, road signs, antique medical supplies, etc. But it’s best known for its collection of beautifully kitschy and sometimes creepy taxidermy (hence the “oddities” aspect of Woolly Mammoth’s name). We’re talking everything from bones and skulls to fetal pigs and bats in mason jars full of formaldehyde. If you’re looking for conversation pieces for your home, this store in Chicago should be #1 on your list.
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