Exploring the Windy City: A Two-Day Itinerary in Chicago

Oh, Chicago. The city known for heavily topped hot dogs, gooey deep-dish pizzas, and being full of windbags (hence its Windy City moniker) is hard to do in just a couple of days. But fear not. As a Chicagoan who loves showing folks around town, I’ve curated a two-day itinerary to make your visit unforgettable. 

Here is an overview of what you’ll do with your short Chicago trip:

Day 1:

• Breakfast at Wildberry Pancakes & Cafe
• Visit the Museum of Science and Industry
• Lunch at Valois Restaurant
• Take a Chicago Architecture Tour along the Chicago River
• Go shopping along the Magnificent Mile
• Dinner at Exchequer Restaurant & Pub
• See a show

Day 2:

• Breakfast at Kanela Breakfast Club 
• Explore Navy Pier
• Lunch at Harry Caray’s Tavern on Navy Pier
• Wander the Lincoln Park Zoo
• Dinner at Geja’s Cafe
• Enjoy music at Winter’s Jazz Club

Day 1 in Chicago

Breakfast at Wildberry Pancakes & Cafe (on Randolph)

When I stay downtown or in the River North neighborhood, I love going to Wildberry for breakfast. There are two Wildberry locations in Chicago, one downtown and one in the Water Tower Place mall off of Michigan Avenue (the Magnificent Mile). My personal favorite dishes here are the to-die-for Cinnamon Roll pancakes and the Breakfast Burrito. 

Visit the Museum of Science and Industry

Although it is a short drive away, I insist that first-time visitors to Chicago see the Museum of Science and Industry in Hyde Park. Not only is this one of the foremost science museums in the world, but it also gives an unparalleled look into Chicago’s past. MSI is housed inside the Palace of Fine Arts building from the 1893 World’s Columbian Exposition, one of only two buildings left from the World’s Fair. 

Lunch at Valois Restaurant

A favorite restaurant of former Hyde Park resident former President Barack Obama, Valois Restaurant is an institution of the neighborhood. Opened in 1921, it is one of the oldest cafeteria-style restaurants in the country. As such, this is an unfussy but delicious comfort food spot. Think Reubens, baked chicken, and lots of mashed potatoes.

Take a Chicago Architecture Tour along the Chicago River

When the weather is right, you’ll see many tour boats tootling along the Chicago River near the Chicago Riverwalk. Don’t be fooled, though; the best one is the Chicago Architecture Center River Cruise. I have taken several tour cruises in the city and this one always takes the cake. This 90-minute tour gently careens along the river, giving incredible insight into the city’s storied history. 

Go shopping along the Magnificent Mile

As you depart the river tour, you’ll be a short walk away from the heart of the Magnificent Mile. This stretch of Michigan Avenue is known as a shopping haven with over 450 stores and countless restaurants. 

Dinner at Exchequer Restaurant & Pub

Chicago’s mobster history remains a big part of its story even a century after prohibition. Exchequer is part of that history as it occupies what was once The 226 Club—a known hangout for gangster Al Capone and his crew. If you want to try deep-dish pizza (a personal favorite), I recommend ordering one here and a cocktail or two. This remains the only place in Chicago I’ve found that makes a decent Brandy Old Fashioned. 

See a show

Often not given the credit it’s due for its role in the performing arts world, Chicago is a city of stages. It is largely known as the birthplace of modern improv but also houses a robust theater community with over 250 companies. No matter what time of year you visit, there is always something incredible to see. 

Day 2 in Chicago

Breakfast at Kanela Breakfast Club 

There are four Kanela locations around the city. The one you want for day two is the Streeterville location, north of Downtown. This casual breakfast spot is a short walk or bus ride to your next stop at Navy Pier. I highly recommend the Kanela French Toast (with lemon créme fraiche) or the Goat Cheese Omelet. 

Explore Navy Pier and grab lunch

Navy Pier is one of those quintessential Chicago attractions that you have to visit. Not only does it offer some of the best views of the city, but it’s also home to the Chicago Children’s Museum, Chicago Shakespeare Theatre, the Centennial Wheel with a bunch of other carnival rides, and dozens of shops/eateries. You don’t have to spend a whole day here, though the variety offers everyone a mix of eats, treats, and things to do. 

Wander the Lincoln Park Zoo

Grab a ride or take public transportation up to the Lincoln Park neighborhood. Here resides the Lincoln Park Zoo, one of the oldest public zoos in the country. LPZ is one of my favorite places in the city because, like Navy Pier, it has incredible views. It also provides serenity in one of the many quiet garden areas, and admission is free!

Dinner at Geja’s Cafe

Just a few blocks away from the zoo is Geja’s Cafe, one of my favorite Chicago gems. In a sort-of wine cellar setting, this is one of the more romantic places in the city, though it is enjoyable for anyone (ages ten and up). This fondue-style restaurant is a great way to end a magical two days in Chicago. 

Practical Tips for Visiting Chicago

If this is your first time visiting the city, I highly recommend staying downtown in The Loop. This will give you a terrific vantage point for not only this itinerary but almost anything you want to enjoy in the city. 

Midwestern weather is unpredictable. That said, your best bet for good visiting weather is to come in April/May or September/October. The temperatures are not too humid, and there shouldn’t be any freak snowstorms. 

Two-Day Itinerary in Chicago Wrap-Up

While two days isn’t enough time to really get to know Chicago, it is a nice introduction to this incredible city. I hope when you fall in love with it as I have that, you come back and get to know its 77 neighborhoods a little better. Feel free to use this as a guide or add to it; there are countless ways to enjoy Chicago. Until then, cheers to good times and deep-dish pizza!

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