Chicago Travel Guide: What to Do, Where to Eat & Stay

Here’s a Chicago travel guide from us, we lived there for 10 years and recently returned from traveling around the world so we see the city with new eyes. Many Chicago travel guides feature the same few things, but we want to add some things that might be off the beaten path, as well as some of the tried and true favorites.

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Go To Where to Stay Here →

Best Activities in Chicago

Let’s start with some of our favorite activities to do in Chicago. Because of the size of Chicago, there are always so many things going on and so many things to do. This Chicago travel guide was written in late 2026 but we tried to pick some timeless activities. These are just some of the things we’d recommend for someone visiting the city for the first time, or looking to try something new if they’ve been to the city and want to change things up.

Chicago River Architecture Boat Tour: There are many companies that do a boat tour on the Chicago River explaining the different historical periods and buildings in the city. It takes about 90 minutes and is available rain or shine, though it’s much better when it’s sunny and you can grab a spot on the top deck. We’ve done this tour more than 5 times and each time we learn something new, because every tour guide has their own interesting facts about the buildings or the city.

The Riverwalk: Before going on the boat tour mentioned above, we absolutely recommend walking down the Riverwalk along the banks of the Chicago River downtown. The Riverwalk starts at Lake Shore Drive and you can walk it all the way through to the south branch of the river, with many bars, restaurants, and shops along the way. This is also a great way to see some of the city’s most iconic buildings if you don’t end up taking the architecture tour. There is a walking historical tour offered here if you don’t want to take the boat tour.

Lakefront Trail: If you want to continue being outside and exploring the city, you can continue from the Riverwalk onto the path along the lakefront and either head south towards some of the museums and Grant Park, or head north and end up at Oak Street or North Avenue Beach. This is a great activity when the weather is nice in the summer or spring/fall.

Chinatown Karaoke: This one is probably not on most people’s lists, but Chicago has a large and bustling Chinatown located south of downtown. There are tons of great Chinese food options, and that is a great meal choice, but one of our favorite activities here is renting a room and singing karaoke with friends! No. 18 karaoke is our favorite place to do karaoke at! There are many private rooms great for renting with a group, and each room has TVs with full internet so you can search for any song you want!

Best Restaurants in Chicago

Now, Chicago has so many different restaurants and so many different cuisines that choosing a few was tough, but we wanted to pick some across the most popular cuisines in Chicago. Here’s our best pizza spots, our best hot dog place, and our best steakhouse. I should note that these are more well known spots but I think you should start here if you’ve never had these cuisines in Chicago.

Best Deep Dish Pizza: Lou Malnati’s. If you’ve never had Chicago deep dish, you have to try it from here. Just make sure to get it for dinner, if you get it for lunch, don’t make too many plans afterwards, because it is heavy and filling! Now, Chicagoans don’t eat deep dish every day, it’s more of something that we get when people are in town visiting, but rest assured that this is the spot to get it from. Pro tip: get the Buttercrust, it’s so flaky and good!

Best Thin Crust Pizza: Robert’s Pizza & Dough Company. This place is more of a place that locals know and has a great location tucked away on an offshoot of the river. It is known for their thin crust pizza, which we absolutely love. Their patio in the summer is fantastic but the rustic brick inside is good any time of the year.

Best Hot Dog: Portillo’s. They’re known for their Chicago dogs and Italian beefs, but the menu has a little bit of everything. This place is a Chicago staple and no Chicago travel guide would be complete without mentioning it! Our recommendation for a first-time visitor is the Chicago dog with all the fixins (mustard, relish, onions, tomato, dill pickle, sport peppers, and celery salt). You absolutely cannot get ketchup on it, Chicago law! and, if you have enough stomach space, You should also order an Italian beef sandwich with giardiniera. These are two Chicago classics and you can’t go wrong with either.

Best Steakhouse: Gene & Georgetti’s, because if there’s something Chicago is known for besides hot dogs, Italian beefs, and pizza, it’s steak! Our favorite is an old-school classic Italian place with a wide variety of steaks and some Italian dishes if you’ve had too much meat at this point! It’s very much a white table cloth kind of place, but doesn’t feel stuffy or too formal. You can’t go wrong with either the bone-in ribeye or the filet, depending on your preference for fattiness on steaks.

Where to Stay in Chicago

If you’re looking at where to stay in Chicago, the neighborhoods closest to the Loop are your best bet. The loop is the central location of downtown and where most of the activities and attractions are. Note that if you’re staying in the loop itself, most everything in the loop closes early and it’s not too lively outside of 9-5 Monday-Friday.

West Loop is full of incredible restaurants and bars, plus easy access to the interstate and public transit, so it’s very convenient to get around. The same can be said about River North, both neighborhoods are walkable to the Riverwalk and the restaurants mentioned above. Some of our favorite hotels are below:

The Palmer House Hotel (One of the most beautiful lobby’s we’ve ever seen and birthplace of the brownie desert)

The Godfrey (Great location and great rooftop cocktails)

Sheraton Chicago Riverwalk (Located directly on the riverwalk with incredible city and lake views in the lakefront rooms)

Hyatt House West Loop (Fantastic location in the west loop)

Final Thoughts

There are so many things to do and see in Chicago, so it was tough to narrow it down to a few places for our Chicago travel guide, but we think these are some of the best things we could think of! Chicago is such a great destination and we recommend spending at least 2-3 days if you’re going on vacation but you could definitely spend much longer and not run out of things to do!

Planning Other Midwest US Adventures?

Check out our loop around Lake Michigan road trip or if you’re looking for a beach destination near Chicago, check out our New Buffalo, Michigan travel guide.

If you have questions about our Chicago travel guide, reach out to us on Instagram @checkedouttocheckin, we’re happy to help!

P.S. – This post contains affiliate links for the hotels we love. If you book directly through these links, we may earn a small commission at no extra cost to you. This helps us keep the blog running!