Chicago

Lifelong native here. You want an Italian beef sandwich.

Architecture tour is well reviewed ( go to )

There's fireworks every Wednesday and Saturday night at the Navy Pier ( go to )

If you want to swim at a beach, Oak St, North Ave, and Ohio St beaches tend to overcrowd ( avoid )

Make sure you're taking the L, it's the safest and least stressful way to get around. Google maps should route you through it pretty intuitively along with the signs. I'd recommend getting out of the loop. Wicker Park and Chinatown are fun places to walk around, eat, drink, etc. Rent a bike or just walk the lake front trail and hang out at the beach for a bit. I personally prefer Lou's for deep dish. Enjoy the event, I'm curious to see how it plays out.

Firstly, have fun! That's awesome you're gonna see the first race here!

If you're staying inside the city limits, you won't need a car. Take CTA and buy a daily or weekend pass.

Lou's is one of the most popular deep dish pizzas, but it's my least favorite. Pequod's is where my heart is, but you'll need a reservation or face a 2 hour wait. Chicago Pizza Oven Grinder Co is unique, and their Mediterranean bread is amazing, but also a major wait (and cash only!)

Take a walk on the lakefront path. It's open all night for walking/running and biking.

Chicago is a city of neighborhoods, so few actually hang out "downtown" after work. Some people live in the Loop, so they do. Things shut down early there. Many neighborhoods have a "main area" that rivals other cities downtowns.

Avoid Giordano’s & portillos, they are both terrible. If you’re around the loop for the nascar thing…Luke’s is a good ‘Chicago sandwich shop’ & as much as Lou Malnati’s sold out it is still decent and easily accessible given where you’ll be at. Also another +1 on the architecture tour..and the Art Institute is well worth it if you’re into that.

Not a native, but have done trips for touristy things.

I like Giordano's for deep dish pizza. The museums are all great, so you could pick any of those that have an exhibit you want to see and have a good time in them. (The Art Institute of Chicago, Shedd Aquarium, Field Museum, and Museum of Science and Industry are my personal favorites). If you're bringing kids, I'd recommend the Museum of Science and Industry over the others as a place to start.

Navy Pier is kind of meh to me, but we have gone in one of the tall ship tours from there and that was fantastic.

You can also check out the CityPASS as a way to get discounted tickets to multiple attractions.

As a note from CityPASS's site, it looks like Shedd Aquarium is closed on July 1-2 due to the NASCAR event you're likely attending, so depending on how long you're staying, that might be a no go.

Any specific interests you have? Food, drinks, museums, sightseeing, etc? There's a ton to do in Chicago and it's hard to give a comprehensive list.

If you are planning the find stuff near downtown, go hang out in the Museum Campus and check out the museums.