Chicago is one of the largest cities in the US, and is incredibly popular with tourists.

Many flock to see the famed Cloud Gate, Millennium Park and more. 

While its known for its bold architecture and museums, it also has a remarkable culinary scene. 

From having breakfast while marvelling at the Chicago skyline to heading on an underground donut tour, there are plenty of options to cater to different tastes.

To get you started, we’ve done some research and curated 19 of the best dining experiences to whet your appetite. 

1. Breakfast in the Sky

There’s no better way to start your day in Chicago with amazing views paired with a hearty breakfast. 

In this dining experience, you’ll head to the tallest building in the Western Hemisphere, and take a seat 103 stories above Chicago. 

This experience allows you to be taking in the breathtaking views of Chicago before the general public. 

Best of all? Besides the views you’ll get to choose from five different breakfasts ranging from an American Breakfast to a Skyline Breakfast and more. 

Once you’re done enjoying the views and savouring your breakfast, you can browse the Skydeck’s interactive exhibits and learn more about Chicago’s history and culture. 

You’re sure to start your day right with this unforgettable experience. 

  • Departure Point: Skydeck Chicago, 233 S Wacker Dr, Chicago, IL 60606, USA
  • Departure Time: 7am to 8am
  • Duration: 1 hour 30 minutes

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2. Chicago Pizza Tour

Chicago has some of the best pizzas in the world, and this tour will take you to the best pizza spots in the area. 

You’ll travel off the beaten path to sample pizza in the various Chicago neighborhoods. 

While tasting these delicious pizzas are certainly a highlight, you’ll also learn more about the science behind ingredient selection and the history behind some of these pizzerias. 

By the end of it all, you’ll understand why pizzas are such an integral part of Chicago’s culture. 

While your itinerary may vary, you’ll typically get to start off at Pizano’s Pizza before ending off at Piece Pizza. 

Come hungry as you’ll be sampling over five different pizzas!  

  • Departure Point: 61 E Madison St, Chicago, IL 60603, USA
  • Departure Time: 11:00 AM
  • Duration: 3 hours 30 minutes

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3. Gold Coast and Old Town Escape

The Gold Coast neighborhood is a historic district with plenty of upscale shopping and dining options. 

The Old Town district on the other hand has plenty of Victorian-era buildings coupled with quaint streets and shops. 

This Chicago Food tour will take you to both districts to sample their delicious foods.

Along the way, your guide will also delve deeper into the architecture and history of these neighborhoods before you stop by at some delectable restaurants. 

As part of this tour, you’ll get to sample a classic deep dish pizza, some of the best tea, and even head to Chicago’s oldest chocolate confectioner and fudge shop. 

This is the perfect tour for foodies that are also looking to learn more about the history and architecture of the area. 

  • Departure Point: 1120 N State St, Chicago, IL 60610, USA
  • Departure Time: 11am to 12pm
  • Duration: 3 hours

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4. Famous Tastes of Chicago

Looking for a tour that has all of Chicago’s staples in one experience? 

You’re in the right spot as this food tour will cover it all. 

Immerse yourself in a 3-hour group walking food excursion in Chicago.

Along the way, you’ll try out five to six of Chicago’s staples, while learning more about the different sights of the city. 

Start off at Pizano’s Pizza and Pasta for a delicious deep dish pizza before enjoying a local chocolate dessert, delicious Chicago Style popcorn, and more.

You’ll even get to visit the famous Billy Goat Tavern that’s made famous from one of the Saturday Night Live’s skit. 

This is one tour that’s covers all the famous Chicago foods, and is sure to satisfy your hunger. 

  • Departure Point: 61 E Madison St, Chicago, IL 60603, USA
  • Departure Time: 11am
  • Duration: 3 hours

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5. Chicago Favorites

When you’re in Chicago, there are some eats that you absolutely must have. 

This extremely popular tour will take you to some of Chicago’s best eats. 

From the quintessential deep-dish pizza to a Chicago-style hotdog, this tour will cover it all. 

You’ll even get to take a look at some of Chicago’s landmarks from Millennium Park to Chicago Riverwalk and more. 

Start off at the world-famous Giordano’s Pizzeria before enjoying a Chicago hot dog, along with numerous other eats. 

You’ll also get to make plenty of stops along the way to take some gorgeous photos with incredible backdrops. 

  • Departure Point: Park Grill, 11 N Michigan Ave, Chicago, IL 60602, USA
  • Departure Time: 11:30am
  • Duration: 2 hours 30 minutes

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6. Underground Donut Tour

Unbeknownst to most, Chicago has some of the best donuts in the US.

This unique underground donut tour will take you to some of the best donut spots, and is a great treat for those with a sweet tooth.

Some of the donuts you’ll get to visit include Dapper Doughnuts, Firecakes, and Doughnut Vault.

Make sure you have plenty of room in your tummy as you’ll be making stops at over four separate donut places.

Your tour will either begin at the French Market or at Do-Rite Donuts and will take place over the course of two hours.

While donuts are included in the cost of the tour, you’re more than welcome to purchase additional donuts to take home as well.

  • Departure Point:
    1: Chicago French Market, 131 N Clinton St, Chicago, IL 60661, USA
    2: Do-Rite Donuts & Coffee, 50 W Randolph St, Chicago, IL 60601, USA
  • Departure Time: 9am or 12pm
  • Duration: 2 hours

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7. Chicago Loop Secret Food Trip

Want to know where all the secret food spots are in Chicago? 

This three-hour tour has you covered and will take you to some hidden gems around the city. 

Your knowledgeable guide will also share with you some fantastic stories about the city, and you’ll get some special insider tips. 

Learn more about how the famous Italian beef sandwich was invented, and how immigrants helped to build up the vibrant food scene. 

You’ll start off at The Loop before heading to the Chicago Riverwalk while also passing by the famous Cloud Gate structure. 

Then, take in views of the Chicago Skyline before passing by the Chicago Cultural Centre and the popular Millennium Park. 

You’ll get several menus to choose from in this tour, while visiting some incredible spots. 

  • Departure Point: 521 S Dearborn St, Chicago, IL 60605, USA
  • Departure Time: 11:30am
  • Duration: 3 hours

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8. Chinatown

You can’t visit Chicago and not head to Chinatown.

This three-hour tour will take you through one of the oldest Chinatown neighbourhoods in America. 

There’s plenty of food on this trip to tantalize your tastebuds and keep you satiated. 

Your guide will also give you a great overview and orientation of the city as you explore the local streets on this walking tour. 

You’ll have tastings from five different restaurants ranging from dim sum to Chinese-style baked goods, Sze Chuan style cuisine, and more. 

By the end of this tour, you’ll be an expert of the different restaurants in the area along with the history of the neighbourhood. 

  • Departure Point: 2217 S Wentworth Ave, Chicago, IL 60616, USA
  • Departure Time: 11:00 AM
  • Duration: 3 hours

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9. Experience Navy Pier Signature Food

The Navy Pier neighbourhood has some of the richest diversity and culinary traditions.

This is an amazing tour that will take you to a variety of authentic food while also visiting some of Chicago’s most iconic landmarks.

On this two-hour walking tour, you’ll learn more about the history of the Navy Pier while also enjoying the delectable food that this neighbourhood has to offer.

You’ll get to sample some stuffed pizza from a pizzeria that started over 200 years ago, try out America’s Dog, enjoy delicious sweets from Brown Sugar Bakery and more.

You’ll even get to savour popcorn from Garrett’s popcorn that opened their first Chicago shop in 1949.

  • Departure Point: 600 E Grand Ave, Chicago, IL 60611, USA
  • Departure Time: 1pm
  • Duration: 2 hours

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10. Chicago Chocolate Tours

There are plenty of chocolate tours to dig into depending on what tickles your fancy.

Valerie’s Chicago Chocolate Tours for example, are a popular tour that takes you around some of the top chocolate shops, bakeries and cafes in Chicago. 

On the two-hour tour you’ll visit a total of four different chocolate shops, bakeries, and cafes. 

You’ll even learn interesting facts about the history and health benefits of chocolate while admiring the architectural sights along the way. 

Alternatively, the chocolate, cupcakes and sweets tour is also a sugar filled tour that will take you to well-known spots such as Ghiradelli and Candyality. 

With five to seven spots to visit, you’re sure to have a sugar rush by the end of this tour. 

This tour even includes a gourmet cupcake at Sacred Grounds Bakery Cafe, and you’ll also get to sample donuts at Do-Rite Donuts.  

  • Duration: 1 to 2 hours

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11. Duneland Wine Country with Gourmet Lunch

Travel to the Duneland area for an unforgettable afternoon of wine tasting along with a luxurious lunch. 

Discover some artisan wineries as an experienced winemaker takes you to three different tasting rooms and provide insight about the area. 

Take some time away from the hustle and bustle of the city and learn from local winemakers about the hybrid grapes grown here. 

End off your relaxing afternoon with a gourmet lunch at Chesterton.  

This is the perfect tour for those looking to know more about wine in the mid-west region while being amongst nature. 

  • Departure Point: InterContinental Chicago Magnificent Mile, 505 N Michigan Ave, Chicago, IL 60611, USA
  • Departure Time: 10am or 11am
  • Duration: 7 hours

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12. Pizza and Cocktails

Everyone knows that Chicago is famous for their pizzas.

Enjoy Chicago’s evening pizza scene like a VIP while also enjoying some drinks.

This bus guided evening tour will take you to visit Chicago through the eyes of a local.

You’ll get to stop at three top-rated pizzerias with either a craft beer or a glass of wine.

Some of the stops includes Exchequer Pizza and Pub with their deep dish and thin crust pizza, and Labriola with their burnt cheese caramelized crust pizza.

By the end of this tour, you’re sure to be an expert on the different pizzas in Chicago.

  • Departure Point: 226 S Wabash Ave, Chicago, IL 60604, USA
  • Departure Time: 7:00pm
  • Duration: 3 hours

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13. Bacon & Brews

What could be better than bacon and beer?

You’ll get to sample both local and international beer on this three-hour walking tour while checking out Chicago’s iconic neighbourhoods.

As you explore Lakeview and Lincoln Park, you’ll also stop at various bars and other places to sample some Midwestern craft brews.

To top it off, three of your beer tastings will also come with three different types of bacon.

Some of the beers you’ll get to sample include local beers at a self-serve beer pub, a British pint, and more.

  • Departure Point: 2816 N Halsted St, Chicago, IL 60657, USA
  • Departure Time: 3:30pm
  • Duration: 3 hours

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14. Bikes, Bites, and Brews

Taste all that Chicago has to offer on a special bicycle guided tour.

On this 14-mile trip, you’ll get to learn more about the history and secrets of this windy city while enjoying some tasty bites along the way.

Some examples of treats you’ll get to savour include a gourmet cupcake, a Chicago-style hot dog and a slice of deep dish pizza.

Travelling on bike means you’ll get to pass through a few different neighborhoods including Wrigleyville, the Lakefront Trail and more.

Don’t forget to snap some pictures when you pass by the beautiful South Pond, North Avenue Beach and Oak Street Beach.

  • Departure Point: 540 N Lake Shore Dr, Chicago, IL 60611, USA
  • Departure Time: 12pm or 5:30pm
  • Duration: 4 hours

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15. Craft Brewery Barrel Bus Experience

This tour is great for craft beer fans and you’ll even get to sit in a special brewery barrel bus. 

You’ll get to visit a total of four different craft breweries on this 3.5 hour tour. 

At the breweries, you’ll also get to tour the various production facilities and enjoy sampling the different local brews. 

Visit a range of breweries from big names like Lagunitas to several smaller breweries. 

All in all, you’ll be consuming about 50 ounces of beer during the tour – which adds up to about four bottles. 

Enjoy the experience, and learning all you need to know about Chicago’s craft beer industry. 

  • Departure Point: 600 N Clark St, Chicago, IL 60654, USA
  • Departure Time: 12am to 8pm
  • Duration: 3 hours 30 minutes

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16. Spirit of Chicago Sunset Dinner Cruise with Buffet

Enjoy a night out in Chicago with a luxury cruise on Lake Michigan. 

You’ll have a splendid time with a delicious buffet dinner, sightseeing, and you can even cap off your night with some dancing.

The cruise will take you through some of Chicago’s iconic sights from Soldier Field to Navy Pier, and even Buckingham Fountain. 

As you marvel at the beautiful Chicago skyline, enjoy your lavish buffet dinner before putting your dancing shoes on as a live DJ spins your favourite tunes. 

  • Departure Point: Navy Pier
  • Departure Time: 6pm to 8pm
  • Duration: 3 hours

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17. Odyssey Dinner Cruise

This dinner cruise is an exceptional experience that will take you through the shores of Lake Michigan. 

You’ll feel like royalty with the newly furnished rooftop lounge and gorgeous interior. 

Your cruise even comes with a three-course plated meal with dishes inspired by celebrity chefs. 

As you enjoy your meal, you’ll have a view of the illuminated Chicago skyline and pass by the Willis Tower and Shedd Aquarium. 

Before your evening ends, you’ll have live DJ entertainment as you continue to dance the night away. 

This is a great dinner experience for those looking to have a relaxing evening while admiring the amazing Chicago views. 

  • Departure Point: Navy Pier
  • Departure Time: 6:30pm to 8pm
  • Duration: 3 hours

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18. Tommy Gun’s Garage Dinner and Show

Looking to be transported back to the roaring twenties? 

Be prepared to be entertained by gangsters and flappers at Tommy Gun’s Garage dinner and show. 

Dance the Charleston to the music of Cole Porter and George Gershwin and prepare to have a fantastic time. 

Start off with a great dinner that includes a wide variety of choices from steak to fish. 

Then, it’s time for for some non-stop comedy and dangerous fun. 

You might even get invited up on stage, so be prepared! 

  • Departure Point: Tommy Gun’s Garage
  • Departure Time: 5:30pm to 7pm
  • Duration: 3 hours

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19. Learn to Make Deep-Dish Pizza

It’s a well-known fact that Chicago is famous for their deep dish pizza. 

Instead of just eating a slice, what if you could make your own pizza and level up your culinary skills? 

In this three-hour intimate group cooking class, you’ll learn how to make an amazing deep-dish pizza from its crust all the way to its core. 

After you’ve completed your masterpiece, you’ll get to taste your own creation and wash it down with a local PBR beer. 

This class is perfect for foodies and those itching to know the secrets to making a deep-dish pizza correctly. 

You can even choose your own toppings ranging from sausage to various veggies and more. 

  • Departure Point: Lawndale Avenue, Lawndale Ave, Chicago, IL, USA
  • Departure Time: 6pm
  • Duration: 3 hours

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These are just some of the top food tours in Chicago. 

If you still have trouble making up your mind, there are plenty more food experiences to discover. 

You can wander through the other neighbourhoods such as Wicker Park and Naperville, or go on a Chicago wine walk. 

Also read:

Find More Food Tours in Chicago

For all new cities, I go overboard on my itinerary, just to see every major attraction. Countries I've visited include New Zealand, Singapore, Hong Kong, China, Cambodia, Japan and Thailand. Mostly Asian countries. Next target - Europe!