10 Things You must HAVE to Try in Chicago Before You Go Home

10 Things You HAVE to Try in Chicago Before You Go Home

You came to Chicago for the marathon. But if all you see is the start line, finish line, and your hotel room, you missed most of the reason to come here.

Chicago is the kind of city where the race can become the excuse for the trip rather than the entire trip. You can run through neighborhoods on Sunday, then come back later to actually explore them. You can pass the skyline during the race, then see it from the river. You can spend one night eating deep dish and another discovering food in Chinatown or Pilsen.

We already have the practical race information covered in our Chicago Marathon Course Guide 2026, Chicago Marathon Prohibited Items Guide, and Chicago Marathon Street Closures and Spectator Guide. We also have a full Chicago Marathon Food Guide and a Chicago Race-Cation Things to Do Guide. This list is different: these are the Chicago experiences we think are worth putting on your personal 'I actually did Chicago' checklist.

Choose Chicago's current bucket list similarly emphasizes iconic food, neighborhoods, architecture, the lakefront, museums, observation decks, and local experiences. So instead of giving you another 30-item tourist list, here are ten that can make a marathon trip feel like a real Race-Cation.

1. Eat Chicago Deep Dish — But Make It an Experience

Yes, we are starting with pizza. You cannot come to Chicago for a marathon and leave without trying the city's most famous pizza style.

For the classic version, put Lou Malnati's on the list. Other established names include Gino's East and Giordano's. If you want a different style of Chicago pizza, try Pequod's Pizza for its caramelized crust or seek out a tavern-style pie.

The important part is timing. Deep dish does not have to be your first meal after the marathon. Save it for later that day or the next day, sit down with your people, order a pie for the table, and make it part of the celebration.

2. Try an Italian Beef and Learn How Chicagoans Order It

An Italian beef is not just something to eat. It is one of those Chicago experiences where knowing the vocabulary makes the meal more fun.

Start with Al's Italian Beef or Mr. Beef on Orleans. Choose Chicago's current guide explains the classic ordering language: sweet peppers, hot giardiniera, dry, wet, or dipped. A dipped sandwich gets the entire thing dunked into the jus.

If you have never had one before, go for the full Chicago experience. Order it how you want, grab plenty of napkins, and accept that this is not a clean food.

3. Eat a Chicago-Style Hot Dog — Without the Ketchup

Chicago has strong opinions about hot dogs. A traditional Chicago-style dog comes with an all-beef frank on a poppy seed bun, yellow mustard, chopped onions, sweet pickle relish, dill pickle, tomato, sport peppers, and celery salt. Ketchup is famously not part of the equation.

For an easy downtown option, Portillo's is one of the recognizable names. Choose Chicago also points visitors toward neighborhood options such as The Wieners Circle in Lincoln Park and Redhot Ranch in Bucktown and Lakeview.

This is a perfect 'quick Chicago moment' between bigger activities. You do not need to build an entire afternoon around it.

4. Walk the Chicago Riverwalk

You should experience the city from the river level, not just from the sidewalk above it.

The Chicago Riverwalk runs through the center of downtown and gives you views of the city's architecture, riverfront restaurants, public art, and bridges.

For marathon travelers, this is one of the easiest items on the list because you can make it as short or long as you want. Grab coffee, find a bench, take skyline photos, and walk only as far as your legs feel like walking.

5. See Chicago From the Water

If you have never been on an architecture cruise, make this the one paid sightseeing experience you prioritize.

Chicago's architecture looks completely different from the river. A boat cruise gives you the skyline without requiring you to walk through every downtown block, which makes it a particularly good post-marathon activity.

Choose Chicago lists architecture river cruises among the city's essential first-time experiences. Book in advance if your trip falls around marathon weekend because popular departure times can fill up.

6. See the Skyline From Above

You have two easy bucket-list choices: Skydeck Chicago at Willis Tower or 360 CHICAGO on Michigan Avenue.

Skydeck is known for The Ledge, its glass viewing boxes extending from the building. 360 CHICAGO gives you views over Lake Michigan and the city from the former John Hancock Center.

You do not need to do both. Pick one based on where you are staying and which view sounds more like you.

7. Explore One Chicago Neighborhood Properly

Do not spend your entire Chicago trip inside the Loop.

Chicago's neighborhoods are a huge part of the city's identity. Pick one and give it a few hours instead of trying to collect five neighborhoods in one afternoon.

For murals and Mexican American culture, choose Pilsen. For Chinese American history, food, shops, and riverfront views, choose Chinatown. For restaurants and nightlife, explore West Loop. For lakefront, parks, and a more relaxed neighborhood day, choose Lincoln Park.

The marathon already gives you a glimpse of several neighborhoods. Coming back afterward lets you see the city without a race clock attached to it.

8. Get the Chicago Mix

Grab a bag of Garrett Popcorn before you leave.

The famous Garrett Popcorn Chicago Mix combines cheese and caramel popcorn. Choose Chicago includes it among the city's iconic must-try foods, and it is one of the easiest Chicago souvenirs to take home.

It is also one of the few things on this list that requires almost zero recovery effort. Pick up a bag, sit down, and snack.

9. Spend Time Somewhere That Feels Like Chicago, Not Just Somewhere Famous

This one is less about checking an attraction off a list and more about getting the feeling of the city.

Spend an afternoon in Pilsen looking at murals. Sit along the lakefront. Wander Chinatown after lunch. Browse shops in Wicker Park. Have coffee in a neighborhood café. Watch people along Michigan Avenue. Go into the Chicago Cultural Center and look up at the architecture.

Choose Chicago's current first-time visitor guide recommends exploring the city's vibrant neighborhoods alongside the major attractions. That is important because Chicago's personality changes dramatically from neighborhood to neighborhood.

You do not need to prove that you 'did Chicago' by visiting every attraction. Pick one neighborhood that makes you curious and actually experience it.

10. Stay Long Enough to Have a Day That Isn't About Running

This might be the most important one.

If your schedule allows, give yourself at least one full day in Chicago where there is no bib to pick up, no start-line transportation to plan, no pace to hit, and no alarm set for a race.

Sleep in. Get breakfast. Drink coffee. Eat something you have never tried. Take a boat cruise. Visit a museum. Explore a neighborhood. Have a long dinner. Talk to the people you came with. Do absolutely nothing for an hour.

That is the part of the trip you are most likely to remember years later.

The Chicago 'I Can't Leave Without Doing This' Checklist

☐ Eat Chicago deep dish.

☐ Try an Italian beef.

☐ Eat a Chicago-style hot dog.

☐ Walk the Chicago Riverwalk.

☐ Take an architecture river cruise.

☐ See Chicago from above.

☐ Explore one neighborhood outside the Loop.

☐ Try the Garrett Chicago Mix.

☐ Experience the lakefront or another local Chicago spot at a slower pace.

☐ Give yourself one full day that is not about the marathon.

How This Fits Into Your Race-Cation

The beauty of doing the Chicago Marathon as a Race-Cation is that none of these experiences has to compete with the race. They can happen before, after, or around it.

You can arrive early and explore. You can race Sunday and spend Monday eating and sightseeing. You can stay an extra night and turn the marathon trip into a mini vacation. Or you can meet other runners through the Sevenly community and build your own group itinerary.

That is why we think about Race-Cations differently at Sevenly. The race gets you there. Your people make it better. The city gives you something to remember.

If you are planning your next race trip, explore Sevenly Travel Race-Cations and start building the whole experience around your race, not just the finish line.

Before You Go Home

Chicago does not need to be rushed.

You do not have to eat every iconic food, visit every museum, climb every observation deck, or walk every neighborhood. Pick the experiences that sound most like you.

Maybe your perfect Chicago trip is deep dish, a river cruise, and a steak dinner. Maybe it is Chinatown, coffee, murals, and the lake. Maybe it is a group of runners sitting around a table after the marathon talking about the race until someone realizes it is almost midnight.

There is no single right way to do a Chicago Race-Cation. The goal is to leave knowing you experienced more than the race.

FAQs

What are the must-try foods in Chicago?

Deep-dish pizza, Italian beef, a Chicago-style hot dog, Garrett Popcorn, and jibarito are among the city's iconic foods. Steakhouse dining and international neighborhood food are also worth adding if you have more time.

What is one Chicago experience I should not miss?

For a first-time visitor, an architecture river cruise is one of the strongest choices because it combines Chicago's architecture and skyline with a relatively low-effort sightseeing experience.

Should I stay after the Chicago Marathon?

If your schedule allows, staying at least one extra day gives you time to experience Chicago without trying to fit sightseeing around race-day logistics.

What Chicago neighborhood should I visit?

Pick based on what interests you: Pilsen for murals and Mexican American culture, Chinatown for food and history, West Loop for restaurants and nightlife, or Lincoln Park for parks and lakefront experiences.

What should I bring home from Chicago?

Garrett Popcorn is an easy edible souvenir. You can also bring home Chicago-themed items from the neighborhoods and attractions you visit.