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

Writing a Chicago Travel Guide came pretty easy to us after living downtown for 10 years! Many Chicago travel guides feature the same few tourist hot spots, but we want to feature a few things off the beaten path that are local favorites!

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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. Our favorite places to grab a bite to eat on the riverwalk include The Northman (beer garden vibes with great beer, pretzels, brats and vegetarian brats!), Taco Rio (Mexican food with great margaritas!), Chiya Chai (incredible Indian-Nepali food with delicious chai, more of a grab and go but can sit anywhere on the river and enjoy!)

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. You can rent a Divvy Bike on the path for only a few dollars to cover more distance. One of our favorite stops for food along the path is Caffe Oliva at Ohio Street Beach and Boat Drinks near Burnham Harbor (awesome live music!)

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 (our favorite is called Triple Crown) 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! 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: Of the most popular deep dish pizza chains, Lou Malnati’s is our go-to! 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: If you’ve never had Portillo’s, you have to try it! 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.

If you are looking for more of local hot dog spot, we LOVE Devil Dawgs. They have the staple Chicago dog but they also have tons of fun topping combos too. Bonus: they can make any dog into a vegetarian hot dog!

Best Steakhouse and Italian: Chicago has no shortage of steakhouses or Italian food and it’s hard to name just a few. But here is a couple spots that we frequent with friends and other locals.

Gene & Georgetti’s 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.

Gibsons is popular for a reason, it’s one of the staple Chicago steakhouses. It’s old school, it’s white table cloth and is delicious. If you want a good classic Chicago steak, this is your spot.

Bavette’s Bar & Boeuf is very well known but nearly impossible to get a reservation to and it’s going pricey (think $500+ for dinner and drinks for 4 adults). But people consistently say this is the best steakhouse in the city.

Club Lucky is traditional Italian with a fun cocktail lounge and outdoor patio. Not only is the food fantastic here but they are very well known with locals for their martini selection! It’s a great option for a large group and definitely not stuffy.

Alla Vita is upscale Italian in a beautiful dining room (very picturesque) with homemade pizza and pasta. Fun for a group but can be tricky to get a reservation if you don’t book in advance. Don’t come here without trying the Wood Fired Table Bread

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 Has one of the most beautiful lobby’s we’ve ever seen. Fun fact about this hotel is that it is the birthplace of the brownie desert! Even if you don’t stay here, you can visit the lobby bar and order a brownie to try out the original recipe.

The Godfrey is in a great location and has a fun rooftop with a variety of cocktails.

Sheraton Chicago Riverwalk is located directly on the riverwalk with incredible city and lake views in the lakefront rooms. This is a great location for being central downtown to everything.

Hyatt House West Loop is a fantastic location in the west loop and walkable to a lot!

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 an island destination is more your style, check out our Guide on How to Get to Mackinac Island.

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!