Chicago is an ideal city to try new foods and drinks. Natives and out-of-towners alike will find something to please their inner foodie. We’ve gathered a few of the most unusual and fun places to eat in the Windy City.


Signature Brunch Cruise on Lake Michigan

Want the best seat in the house? Every table offers this when dining on Lake Michigan. Take a panoramic brunch cruised paired with world-class cuisine and you can’t go wrong. Spend your afternoon on the water with picturesque views while enjoying DJ entertainment and an assortment of games. Feast on a chef-prepared brunch buffet, and a fully stocked bar, and celebrate in style with open-air rooftop decks with sweeping skyline views. Imbibe with bottomless mimosas or creative cocktails available for purchase and grab a window table with reservations for the ultimate experience. 

If you need help deciding which one to visit, consider a food tour. You’ll get to sample dishes from several establishments, learn more about Chicago’s rich (and tasty) heritage, and have a memorable experience with your group.


Chicago deep-dish pizza


West Loop Pizza Walk

The West Loop is a thriving foodie haven. It’s home to the best of Chicago’s pizza parlors—and this tour takes you on a walking tour to sample them all. Learn about the city’s ten styles of pizza and its history from a dough-centered guide. You’ll also get caught up on the history of the West Loop and some of its colorful characters.


Signature Lunch Cruise on Lake Michigan

Looking for something for the entire family? A small gathering of friends? Perhaps, a romantic afternoon for two? A lunch cruise is a perfect way to see Chicago from the water! Glide along Lake Michigan while enjoying DJ-curated music and let the breeze take you away. If you’re celebrating a special occasion, check out the packages that are available to toast the event. 



Alinea is a Michelin-starred restaurant that serves molecular gastronomy and experimental cuisine–which means they use cutting-edge scientific techniques to improve traditional cooking methods. It’s a popular destination for locals and tourists alike. Alinea also offers cooking classes where you can learn how to recreate their signature dishes at home.


Superdawg Drive-In

Superdawg Drive-In is a classic for Chicagoans. It’s been around since 1948, and to this day, it’s still packed with people who come to eat and hang out. The hot dogs are delicious, the burgers are good, and the shakes are amazing.


A beer tap with a beer glass being filled

Kaiser Tiger

If you love German food and beer, Kaiser Tiger is the place for you. This offbeat restaurant serves traditional fare (schnitzel, sauerbraten, and sauerkraut) in a casual, festive setting with more than 100 varieties of beer on tap. The space is extensive—with a capacity of 250—and there’s a small craft cocktail list if that’s more your thing.

Kaiser Tiger opened in 1986 as a bar with a few tables near Chicago’s Lincoln Park neighborhood. Today it has three locations: Lincoln Park, Old Town, and River North. All three serve the same menu and have similar decor. Still, each has unique features, like outdoor seating at the River North location.


Girl & The Goat

If you’re looking for unique, look no further than the West Loop to check out Girl & The Goat. This is Stephanie Izard’s first restaurant with Boka Restaurant Group since winning Top Chef Season 4. The family-style restaurant has seating for 122, and the menu is divided into meat, fish, and vegetable categories and offers wine selections from around the world. The menu features globally influenced bold flavors in a fun and lively setting with banquettes, dimly lit corner nooks, and elevated platform seating. Munch on pull-apart pretzels or chickpea fritters before trying some of their most unique dishes such as goat belly, liver mousse, sticky glazed pork shank, or the green beans in a fish sauce vinaigrette. If you’re feeling especially adventurous, try the roasted pig face, and don’t be afraid to ask your server questions! 


Kit Kat Lounge & Supper Club

Kit Kat Lounge & Supper Club is a restaurant and bar with an upstairs speakeasy.

The Kit Kat Lounge & Supper Club has been around since 1934 when it was known as the Kegel Tap Room. The bar closed during Prohibition and reopened after the law was repealed in 1933—but this time as a speakeasy.


Closeup of the Chicago Theatre sign



Carnivale is a Brazilian steakhouse on Montrose Avenue that has everything you desire in a restaurant: great food, excellent service, and a fabulous atmosphere.

The restaurant’s menu offers all kinds of meat cooked to perfection by their expert chefs. Carnivale is also known for its delicious caipirinhas—a potent drink made with cachaça (Brazilian rum) mixed with fruit juice.


The Wiener’s Circle

The Wiener’s Circle, located in Chicago’s Ukrainian Village neighborhood, is a hot dog joint that has been around for decades that’s popular for its Chicago-style hot dogs. It has a relaxed and casual atmosphere where you order food at a counter and then find a seat inside or outside. If you go on the weekend, expect to share tables with other customers who are just as enthusiastic about their dogs as you are.

If you want a different experience than just eating one type of hot dog, The Wiener’s Circle also serves up vegetarian options, such as veggie dogs and fries. There are also several beer choices available at this restaurant if you want something other than soda with your meal.


Why Chicago is Home to So Many Fun Places to Eat (2024 & 2025)

Chicago, renowned for its architectural marvels and vibrant cultural scene, also boasts an incredibly diverse and dynamic culinary landscape that makes it a paradise for foodies. The city’s reputation as a hub of gastronomic delights is well-earned, with its myriad of fun places to eat spanning a vast array of cuisines, atmospheres, and dining experiences. Here’s why Chicago is celebrated for its entertaining and eclectic dining options.

At the heart of Chicago’s culinary appeal is its rich multicultural heritage, which is reflected in the breadth of its food offerings. From the authentic Mexican taquerias in Pilsen to the aromatic Indian restaurants in Devon Avenue’s Little India, the city is a mosaic of global flavors. This cultural melting pot allows diners to embark on a culinary world tour without leaving the city, making each dining out experience a unique adventure.

Chicago’s innovative dining scene is another reason the city shines as a foodie destination. Local chefs are known for pushing boundaries and experimenting with flavors, techniques, and presentation, turning meals into memorable experiences. Whether it’s the avant-garde dishes served at high-end restaurants or the creative twists on classic Chicago street food, the city’s culinary offerings are as diverse as they are innovative.

The city’s food scene is also characterized by its fun and laid-back dining atmospheres. From rooftop bars offering panoramic views of the skyline to cozy, underground speakeasies, Chicago’s restaurants and eateries provide settings that enhance the dining experience. Seasonal food festivals, open-air markets, and neighborhood food tours add to the city’s lively food culture, offering both locals and visitors endless opportunities to explore and indulge.

Chicago is home to some iconic dishes that have become integral parts of its identity. Deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches are just a few of the must-try local specialties that draw people into the city’s eateries. These beloved dishes are not just food; they’re an experience, often served in bustling, jovial environments that embody the spirit of Chicago.

Chicago’s status as a foodie haven is due to its diverse culinary offerings, innovative dining experiences, and the fun, engaging atmospheres of its restaurants. The city’s blend of cultural influences, coupled with its adventurous chefs and iconic dishes, makes dining out in Chicago an endlessly exciting adventure. Whether you’re in the mood for a gourmet meal, a casual bite, or a unique culinary experience, Chicago’s dining scene promises to deliver, making it a true playground for anyone who loves to eat.


FAQs – Fun Places to Eat in Chicago

Why is dining with City Cruises a unique experience in Chicago?
City Cruises offers a distinctive dining experience by combining gourmet cuisine with stunning views of Chicago’s skyline from the Chicago River or Lake Michigan, making it a memorable way to enjoy the city’s beauty.

What types of dining cruises are available with City Cruises in Chicago in 2024?
City Cruises in Chicago offers a variety of dining cruises, including brunch, lunch, and dinner options. They also provide themed and holiday cruises for a unique dining experience on the water.

How does a dining cruise on the Chicago River differ from Lake Michigan?
A dining cruise on the Chicago River offers a close-up view of the city’s famed architecture, while a cruise on Lake Michigan provides broader, panoramic views of Chicago’s skyline and the lakefront.

What kind of menu can I expect on a City Cruises dining cruise in Chicago?
City Cruises’ dining cruises in Chicago typically feature a variety of menu options, from casual fare to gourmet meals, including seasonal and locally-sourced ingredients.

Can City Cruises accommodate dietary restrictions for dining cruises in Chicago?
Yes, City Cruises can accommodate various dietary restrictions. It’s advisable to inform them of any dietary needs in advance when making your reservation.

Are City Cruises’ dining cruises in Chicago suitable for celebrating special occasions?
Of course, City Cruises provides an elegant and unique setting for celebrating special occasions, complete with exceptional food, stunning views, and a festive atmosphere.

What types of fun dining experiences can I find in Chicago?
Chicago offers a diverse range of fun dining experiences including rooftop restaurants with city views, themed diners, eateries with live entertainment, and unique spots like riverfront cafes and bistros.

Are there any iconic foods I should try in Chicago?
Definitely! When in Chicago, try iconic dishes like deep-dish pizza, Chicago-style hot dogs, Italian beef sandwiches, and Garrett Popcorn.

Can I find international cuisine in Chicago?
Yes, Chicago’s culinary scene is diverse, offering a variety of international cuisines including Mexican, Italian, Asian, Middle Eastern, and more, reflecting the city’s rich cultural tapestry.

Are there family-friendly fun dining spots in Chicago?
Chicago has many family-friendly restaurants that offer fun atmospheres and menus suited for children, such as themed restaurants and places with interactive dining experiences.

What are some unique dining locations in Chicago for a special occasion?
For special occasions, consider dining at one of Chicago’s upscale steakhouses, a restaurant with a view of the skyline, or a historic Chicago establishment like The Berghoff.

Original post date: November 16, 2022