Everything you need to know for a weekend in Chicago

By Audrey Tuttle | Posted: April 18, 2025

I got to spend a few days in Chicago over a long weekend and I loved every minute! The vibes there were much friendlier than I’ve experienced in other major U.S. cities, and that started before we even arrived, with us meeting a friendly Chicagoan on our flight who gave us some great recommendations! 

Throughout the weekend I got the sense that the people of Chicago were proud to be from there, and after visiting I can see why! It’s a super fun place and I would recommend it to anyone looking for a city with friendly people, delicious food, interesting history, and exciting energy!

Places to see and things to do

I recommend the Go City Chicago pass if you want to hit some of Chicago’s most popular attractions. Many activities listed below were included on this pass, so if they interest you, you can save hundreds with the pass!

You still have to make a reservation/choose a time slot for some of the Go City pass activities. Make sure you check this ahead of time to make the most of your pass and fit in as many activities as possible. 

Millennium Park 

This park is home to the iconic Cloud Gate sculpture, better known as “The Bean.” I can’t explain why I was so excited to see The Bean but it’s been on my bucket list for ages. The park is free to enter, so grab your deep-dish pizza to go or get a meal from one of the vendors at the park, and enjoy a nice picnic while people-watching at the park.

Skydeck Chicago

Skydeck is located at the top of the Willis Tower (formerly the Sears Tower). This is the tallest building in Chicago, and was at one point the tallest building in the world. We booked a time slot in the evening, allowing us to watch the sunset from this amazing viewpoint. On your way up to the Skydeck, there’s a cool museum full of immersive exhibits. You can learn about Chicago’s origins, the Great Chicago Fire, the architectural history, the culture, and more!

360 Chicago

This observation deck is located on the 94th floor of the John Hancock Center, another of Chicago’s famous skyscrapers. At the top, you can visit the CloudBar to grab a cocktail, mocktail, or snack and enjoy the incredible views of the city. 

River architecture cruise

This was one of my favorite things we did in Chicago! Several companies offer tours like this, but we went with the company included in the Go City pass. The guide on the boat was funny and informative, and we could admire the skyline and learn about the iconic Chicago architecture as we cruised the river.

Adler Planetarium

This probably wouldn’t have been on my radar if it hadn’t been included on the Go City Chicago pass, but I’m glad we went! It has some cool exhibits and interesting shows throughout the day.

Ferris wheel on Navy Pier

Navy Pier is a spot that draws tourists from all over the world, and for good reason! There are great views of the city and a fun atmosphere that reminded me of going to the carnival as a kid. Our riverboat tour departed from Navy Pier, so when we got back, we decided to hang around and take the ride on the Ferris wheel, which was also included in our Go City pass. On the pier, you can also get the original Rainbow Cone ice cream, visit the Chicago Children’s Museum, go shopping, and more. The food is definitely tourist-priced, but it’s a fun place to spend an evening. They also have a lot of fun events like dance performances and fireworks shows throughout the year, so check out the calendar on their website to see what’s going on when you’re in town! 

Flyover Chicago

Flyover Chicago (also located on Navy Pier) was so cool. If you’ve ever been on the Soarin’ Around the World ride at Disneyland, it was similar to that, but specific to Chicago. Not to be dramatic, but I want something like this created for every city in the world. It was such a cool way to see Chicago’s sights and to learn about the city’s history and culture. 

Riverwalk stroll and restaurants

If you stroll along the Chicago River, you can find plenty of cute cafes. Even if you’re not stopping for food, you can sit on the steps along the river to relax and enjoy the views of the city’s skyscrapers and the boats floating past. 

White Sox or Cubs baseball game

Chicago has two major baseball teams, and you’ll want to catch a game if you’re in town during the season! I had originally hoped to see a Cubs baseball game because I’ve had friends recommend visiting the famous Wrigley Field, but the team was away the weekend I was in town. We ended up going to a White Sox game and it was so much fun! It was an exciting evening surrounded by delicious food, good vibes, and passionate fans.

Magnificent Mile

Chicago’s famous Magnificent Mile is Chicago’s shopping district. This impressive stretch is full of opportunities for luxury shopping and fine dining. But even if those aren’t your thing, it’s still fun to walk around, take in the exciting energy, and admire the architecture!

Hop-on hop-off bus

A hop-on hop-off bus is a classic tourist activity, but if you’re only in town for a couple of days you might as well embrace that and have some fun riding around on these double-decker buses! They have stops at most of the city’s major sights, and it’s a fun and different way to observe the city while driving around!

Food to try

If you’re like me and one of your favorite parts of traveling is trying all the different foods, then Chicago will NOT disappoint. I was worried the food there might be a little heavy for me because deep-dish pizza and Italian beef sandwiches aren’t my everyday diet, but almost every single meal I had there was a 10/10!! Here are some restaurants and meals I would recommend while you’re in town:

Lou Malnati’s and Giordano’s deep-dish pizza

These two pizza places are both great spots to try the famous Chicago-style deep-dish pizza. The winner between the two is a hot topic debate, so I won’t get all political on you by saying which one is best. You can do your own delicious research by trying these two or another one of the countless deep-dish pizza spots in Chicago to find your personal favorite! Both restaurants have many locations throughout the city, but lines can be long so either make a reservation or plan on spending some time waiting.

Chicago-style hot dog 

Normally, I’m not a hot dog girlie but this is definitely one worth trying. Chicago-style means an all-beef hot dog on a poppy seed bun topped with mustard, white onions, relish, a pickle spear, tomato slices, sport peppers, celery salt, and NEVER ketchup. I got mine while attending a White Sox baseball game and I felt like I was having a classic American experience. 

Italian beef sandwich

Another famous Chicago meal that exceeded my expectations was the Italian beef sandwich. I tried mine at Giordano’s and it was probably my favorite meal in Chicago! If you’re a fan of the TV show The Bear, the restaurant in the show was based off a little sandwich shop in the city called Mr. Beef. Sadly I didn’t have time to make it there while I was in town, but I’ve heard their Italian beef sandwich is worth trying!

Chinatown

We spent a while one afternoon exploring Chinatown, and we sampled dishes from a few of the different restaurants and dessert shops. Chicago’s foodie scene doesn’t just apply to pizzas and hotdogs since there were tons of restaurants in the neighborhood with amazing ratings! 

Flights tips

There are two major airports in Chicago (MDW and ORD), so check both options to see which will be the better deal and have the better itinerary for you!

The cheapest flights will likely be with a budget airline, but it’s definitely worth it for such a short flight! If you’re just taking a quick weekend trip, you might be able to pack light enough to avoid any extra baggage fees the budget airlines might have. If you are planning to check a bag, pay for it when you book the ticket! It will be much cheaper if you pay for it upfront instead of adding it later.

We ended up booking an Allegiant flight from PVU to MDW. It was my first time visiting the Provo airport, and I loved it!

Accommodations

I initially planned on getting a hotel in downtown Chicago, but we were in town the same weekend as a large national conference so things were pretty booked out. I’m sure there are some great options for staying in the city, but we booked an Airbnb in the nearby neighborhood of Bridgeport and loved it! Bridgeport had some great restaurants, felt very safe, and we were within walking distance of bus stops and train stations making it easy to get into the city. 

Tip: If you plan to use public transit, use the map feature on Airbnb to see where the nearby subway stations and bus stops are. This will help you to find a place to stay where you can easily travel into the downtown area. 

Transportation

The public transit ran frequently and it was easy to get around on. If I went back I would do the same thing again.

You can buy a transit pass called a Ventra Card and can load on individual rides, or get a pass for unlimited rides! They have a 1-day, 3-day, 7-day, or 30-day unlimited ride pass. We got the 3-day pass for just $15! You can also add your Ventra card to your Apple or Google wallet so it’s super easy to tap on and off the buses and trains.

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