Chicago Race Weekend Travel Guide: Where to Stay, Eat, Drink & Explore
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Whether you’re visiting the Chicagoland Speedway or in town for the NASCAR Chicago Street Race (anticipated to return in 2027), this guide will easily help you to fill up a long-race-weekend itinerary with hearty Midwest eats and fun activities in the heart of the Windy City.
NASCAR in Chicago also means it’s summertime in Chicago! In addition to the roaring hum of race cars, get ready to experience activities like watching fireworks at Navy Pier, spending 4th of July at Wrigley Field for a Cubs game, and eating an ice cold Original Rainbow Cone to cool off in the weather.
An exciting long weekend in Chicago awaits!
Where to Stay in Chicago for Race Weekend
Our top pick of where to stay at in Chicago is the Hyatt Regency – the hotel we based ourselves at during our first trip to Chicago for the NASCAR street race. It’s very centrally-located to all the main Chicago sights, has several dining options, and is a great spot to use Hyatt points to help cover your stay!
Pros of the Hyatt Regency
- Excellent central location right across the street from the Chicago River
- 12-min walk to Cloud Gate (aka “The Bean”) at Millennium Park
- 8-min walk to the Architecture River Tour boat stop (included with the Chicago City Pass)
- 20-min walk to Navy Pier
- Less than 15 mins to walk to the NASCAR street race entrance
- Countless restaurants within walking distance
- Great for Hyatt loyalists to use points/award redemptions
- Several onsite bars and restaurants
- SIXT Rental car kiosk inside the hotel! This is perfect for day-rentals to drive out to a Chicagoland race. Exploring the city otherwise doesn’t require having a car, so it’s very convenient to have this option for race-day transportation.
Book the Hyatt Regency on Hotels.com, Booking.com, Expedia or Direct
Off Track Exploration in Chicago
As I mentioned above, Chicago is packed with things to add to your NASCAR race weekend itinerary – especially if it’s your first time visiting the city! Here’s a list of some of the main attractions that are worth adding to your list.
Chicago City Pass – Worth It?
Firstly, let’s talk about the City Pass, which you will undoubtedly come across when researching travel to Chicago. Is it really worth it? Honestly, their cost savings numbers posted on their site are a little inflated. We priced what we wanted to do/see and it actually came out to around equal what we would have paid separately for each activity.
However, it is very convenient to have the app with all your selected activities in one place. Because of this, I do recommend getting the City Pass if you’re thinking of doing four to five main activities on their list.
Millennium Park & The Cloud Gate (aka “The Bean”)
You can’t go to Chicago and not see “The Bean.” This work of art known as The Cloud Gate is pretty impressive and located right in the middle of Millennium Park. Walking around the sculpture is more than just seeing reflections of yourselves, it’s also about admiring the reflection of the city skyline. It’s cool at any time of day!
Note: During 4th of July weekend, there may be special events or concerts in the park, which require you to pass through security screening to get into the park. Entry to the park is free though.
Architecture River Boat Tour
Chicago is a city filled with beautiful buildings and the best way to see them is actually from the Chicago River. There are several boat companies offering tours, but we booked with the company that was included in the Chicago City Pass – Shoreline Sightseeing. It was a highlight of our time in Chicago!
For the best light, a lot of people recommend earlier mornings or around golden hour/sunset. I can tell you in the middle of summer (when you’d be visiting for the NASCAR race) it can be hot in the city and you don’t want to be sitting in the sun. We did the 10 a.m. tour and it was already very warm.
Book your architecture tour with Chicago City Pass or Viator
Field Museum
We aren’t big on history museums when we travel, but the Field Museum is truly impressive! The Field Museum is a natural history museum with a collection of millions of artifacts. Only a fraction of the collection is on display and it will still take hours to wander through.
Our favorites at the Field Museum were the animal specimens (collected from all over the world) and the dinosaur fossils, including Sue the T-rex, one of the largest T-rex fossils ever discovered.
Plan to spend at least three to four hours in here to try and cover everything.
We booked our tickets with the Chicago City Pass but you can also walk in and get tickets or purchase online ahead of time.
Art Institute of Chicago
I say we aren’t big on museums, but when it comes to art museums, I (Moani) am more of a fan. However, I am very particular about the kind of art I like – generally impressionist and post-impressionist art from painters like Seurat, Van Gogh, and Monet.
In fact, the main reason why we visited the Art Institute of Chicago was to see one of Georges Seurat’s most famous paintings Sunday Afternoon on the Island of La Grand Jatte, which many people might recognize from the movie Ferris Beuller’s Day Off. It happens to be one of my all-time favorite paintings, so we got to check that off the bucket list!
This art museum is full of paintings and art works from all eras and is massive. It’s another one you want to dedicate a few hours to if this type of museum is of interest.
We booked our tickets with the Chicago City Pass but you can also walk in and get tickets or purchase online ahead of time.
360 Chicago at John Hancock Tower
With Chicago being a city full of skyscrapers, you’ve got to pick a tower to see the city from above! There are two main towers that are deemed “tourist attractions” – the John Hancock Building with its 360 experience and the Willis Tower’s Skydeck (formerly known as Sears Tower).
If you only have time for one tower, we preferred the 360 experience at John Hancock. We enjoyed the views more (including of Navy Pier and the city’s coastline) and they have the Cloud Bar where you can grab a drink (albeit an expensive one) to linger and admire a 360-degree view of Chicago.
The 360 experience does have an optional add-on called The Tilt if you’re looking for an adrenaline-inducing experience where a small portion of the building tilts above the city while you hang on and peer through the glass. We didn’t do this (hello, fear of heights), but we did watch others. Some chickened out as it started to move, but it only lasts for a minute or so!
Also, if you plan to visit on a Wednesday or Saturday, you could consider a nighttime visit to see the fireworks at Navy pier at 9:00 p.m. on Wednesdays or 10:00 p.m. on Saturdays. It has the perfect view of the pier for this!
We booked tickets online ahead of time, which I highly recommend doing especially during busy summer months. This experience is also in the City Pass if you have room to select it.
Skydeck at Willis Tower
Even though we preferred the 360 experience at John Hancock slightly more, Willis Tower, formerly known as Sears Tower (and still the locals’ preferred name), is an iconic skyscraper to add to your visit list.
Once the tallest building in the world from 1973 to 1998, it now sits in 26th position – though it is still the 3rd tallest building in the United States.
Aside from the city views, the big draw here is The Ledge – several glass window pods that stick out from the building that have become a popular photo op. Depending on the size of your group, you only get a limited amount of time here in order to cycle through the groups quicker.
If you have a fear of heights, don’t look down! Otherwise, The Ledge is definitely a must-do when visiting the Skydeck.
We booked our tickets with the Chicago City Pass, which comes with Expedited Entry, special VIP elevator access, and an expedited line for The Ledge. You can also walk in and get tickets, or purchase them online ahead of time. I highly recommend Expedited Entry tickets, especially when it comes to standing in line for The Ledge.
Catch a Cubs Game at Wrigley Field
If you’re a baseball fan (actually, even if you aren’t) catching a game at Wrigley Field is a quintessential Chicago experience. It was probably our favorite off-track activity we did in Chicago!
The NASCAR race in Chicago is typically scheduled around 4th of July weekend and I highly recommend going to a game on the actual 4th if possible. The vibe is incredibly patriotic, there’s pre-game events like a parade with appearances by clydesdales horses, and even a jet flyover.
Going to a ballgame at such an iconic stadium is just plain cool.
Wrigley Field Tips
- Take the Red Line “L” train from the city center up to Wrigleyville and get off at Addison
- There are a bunch of bars and restaurants in the Wrigleyville area you can visit before or after the game as well (I recommend grabbing donuts at Do-Rite pre-game).
- Get a DIY Chicago dog to enjoy at the game!
Fireworks at Navy Pier
In the summer, catch a free fireworks show at Navy Pier every Wednesday at 9:00 p.m. and Saturday at 10:00 p.m. from Memorial Day to Labor Day. The best place to watch the fireworks is at Navy Pier itself, or you can go up the John Hancock Tower and watch them at 360 Chicago from above!
Harry Potter Chicago
If you’ve got kids in tow, or hey – even if you’re big kids like we are, the Harry Potter Shop in the Magnificent Mile is pretty epic! Truth be told, we happened up on this by accident and I (Moani) am a big Harry Potter nerd. I had to drag my entire crew through the store for nostalgia-sake.
Not only is it a gift shop, they also have a Butterbeer bar and Chicago-exclusive Butterbeer popcorn. Had we not just stuffed ourselves to the brim with deep dish pizza at Gino’s, we would have been right there.
Our Chicago Restaurant Picks
Chicago has a solid list of iconic eats to have when visiting the city, from hearty deep dish pizzas and Italian beef sandwiches drenched in jus, to Chicago hot dogs, specialty ice creams, and even donuts!
Be sure to pack lots of stretchy pants for this trip.
Chicago Deep Dish Pizza
Deep dish pizza is a signature Chicago food and there are a handful of popular restaurants specializing in this overindulgent dish scattered about the city.
Our Pizza Picks
- Gino’s East: If you only go to one spot in Chicago, let it be Gino’s East at their Magnificent Mile location! They excel in all categories from crust and sauce to the perfect toppings ratio. Get the Gino’s Supreme with sausage and the antipasti salad.
- Lou Malnati’s: Our second place pick is Lou’s for their ultra buttery crust. While Gino’s edges out Lou’s slightly, it’s still a good pick. Lou’s also sets up shop at the NASCAR Chicago Street race if you need a pizza fix on race day.
- Giordano’s is a solid alternative to Gino’s and Lou’s, known for their pizzas being generously stuffed with cheese.
There is also Pequod’s – another Chicago favorite, which we haven’t been to so we can’t accurately rank it. However, we hear it’s delicious!
Pro Tip: Try to get reservations at these restaurants or go during off-peak hours to avoid long waits.
Italian Beef Sandwiches
Another hearty favorite in Chicago is the Italian beef sandwich – a savory and sometimes lil spicy sandwich depending on the peppers you add. Our order at each spot: dipped with both sweet and hot peppers!
Our Italian Beef Sandwich Picks:
- Portillo’s: A Chicago staple, Portillo’s is an excellent choice for Italian beef sandwiches right in the heart of the city.
- Johnnie’s Beef: It may be a bit of a trek, but Johnnie’s in Elmwood Park has the best Italian beef in the Chicagoland area (at least according to us). We actually ate five different Italian beefs in one trip to find the best in Chicago. Johnnie’s is worth the trip! Note that Johnnie’s is cash only.
- Chef Ciccio: For a non-traditional Italian beef sandwich, head to Chef Ciccio at Navy Pier for an Italian beef served in artisan bread with a rich and flavorful jus.
Chicago Dogs
Calling all hot dog lovers – you need to have a traditional Chicago dog when in Chicago!
Known for their “drag it through the garden” style, Chicago dogs are topped with mustard (never ketchup – don’t even ask), white onions, relish, pickle slices, tomatoes, sport peppers, and celery salt and stuffed into a poppyseed bun.
Our Favorite Chicago Dogs:
- Portillo’s: Aside from their delicious Italian beefs, Portillo’s has killer hot dogs. The best part? You can get a jumbo dog here, which we highly recommend for more of that hot dog flavor.
- Wrigley Field: Hot dogs and baseball go hand in hand, and at Wrigley Field, their Chicago dogs are DIY style. This means you can put as much of each topping on your dog as you want (in our case, extra sport peppers please!).
- The Northman: While The Northman doesn’t have the best dog in the city, they do have one of the best views to enjoy a Chicago dog! Located right on the River Walk, this is the perfect spot to grab a hot dog, sip a beer or cider, and take in city views.
Sweet Treats
When you need a break from all the hearty savory foods in Chicago, turn to some Chicago favorites to help give you a little balance.
- The Original Rainbow Cone: With several locations in the city (though I recommend Navy Pier), pay a visit to The Original Rainbow Cone and get the OG with chocolate, strawberry, Palmer House, pistachio & orange sherbet. It is the best treat for that Chicago summer heat.
- Stan’s: Chicago is a great donut city but our top pick goes to Stan’s, which has several locations scattered all throughout the city. Get one of their croissant donuts or their Biscoff Pocket and thank me later.
- Do-Rite: Another prime spot for donuts in Chicago is Do-Rite, also with many locations in the city. We recommend the Wrigley Field location for a pre-game snack. Get the buttermilk old fashioned or the raspberry Bullseye (seasonal). They also serve fried chicken for something savory!
Other Chicago Foodie Spots
While Chicago is known for their staple foods of pizza, Italian beef, and Chicago dogs, the city is an all-around great place to be for a foodie. If you have time to fit in a meal outside of its iconic foods, here are some more recommendations:
- The Dearborn: For a nice dinner out, make a reservation at The Dearborn. Some things to get: the Midwest fried chicken, fish and chips, and do not skip the Parker House rolls.
- Garrett Popcorn: If you’re a popcorn lover, Garrett is a Chicago institution. Our favorite is the caramel corn, but many swear by the sweet and savory “Garret Mix” of cheddar + caramel corn.
Did you find this NASCAR Chicago race weekend guide helpful? What will you be putting on your Chicago itinerary?
