Best Things to Do in Chicago for First Timers: The Ultimate Bucket List

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So you’ve booked your first trip to Chicago and are probably wondering just how much you can fit into your trip. The answer is – a lot! Downtown Chicago is filled with so many great things to do, from admiring the city’s incredible architecture to stuffing yourselves silly with the heartiest foods you can imagine.

The best things to do in Chicago for first timers are mostly all located in a relatively compact area too. We were able to get around to most things on foot with a few Ubers and an “L” Train ride.

We spent five nights in the city on our first trip, but one of our days was mostly dedicated to the NASCAR Street Race. So, in theory, you could really pack all these things on my list into a four-night trip with some strategic planning.

We had a blast fitting in all of the city’s highlights from this guide in one trip and I’m sure you will too!

Where to Stay in Chicago

For our first visit to Chicago, we stayed at the Hyatt Regency, which has the perfect location right in downtown Chicago. Truthfully, I chose this hotel because we could use Chase points that easily transfer to Hyatt. After staying here on points, I can confirm it was an excellent choice that I’d pay cash for too.

The Hyatt Regency is located right across the street from the Chicago River and the Riverwalk, which is the best place to spend an evening in the city! If you can, ask for a room with a river view.

With a central location, walking is a breeze to neighborhoods north of the river, including River North, Streeterville, Magnificent Mile, and Navy Pier. It’s also just as easy to get to areas south of the river, including Millennium Park and South Loop. The Field Museum area might be a bit of a stretch on foot at close to 40 minutes, but it is doable if you like to get your steps in.

The Hyatt Regency also has several bars and restaurants onsite if you don’t feel like venturing out. Although, there are a ton of restaurants in the immediate area or within a decent walking distance.

How to Get Around Chicago

Chicago is a pretty big city, but if it’s your first time visiting, public transportation and taxis/rideshares will serve you just fine. Most activities best for first-timers in Chicago are going to be condensed right in the downtown area!

Uber/Lyft/Taxis: Taxis and rideshares are easily available to/from the airport. Be aware that during rush hour times, it can take up to 2 hours to get to/from the O’Hare airport (speaking from experience). Once in the city, this is an easy way to get around for places that are a little too far to walk to.

Train: If you love train travel, you can take the “L” train’s Blue Line between O’Hare and downtown Chicago. It will also take you to some prime locations from downtown, like Wrigley Field, with less hassle than going by car.

Walking: Pack your comfy shoes because exploring Chicago by foot is my favorite mode of transportation! And you’re gonna want to burn as many calories as possible after consuming all the delicious food the city has to offer.

Water Taxi: These typically only operate in warmer months (i.e May through Labor Day), but are a fun, alternative way to get from place to place via the river. Shoreline and Chicago Water Taxi are two options that provide this service.

Chicago CityPASS – Worth It?

Before we dive into all the best things to do in Chicago, you’re probably going to come across the Chicago CityPASS a lot when planning your trip. You might wonder – is the cost is worth it?

For my group, I priced out each activity we wanted to do and compared it to the pricing on the CityPASS and it came out to about even (even though the CityPASS website will claim a higher dollar amount in savings).

That being said, the convenience of the CityPASS is definitely beneficial and why I recommend getting the pass if you want to do four to five activities. The app includes the ability to make reservations for each attraction and stores your tickets for your whole party. This could not be any easier!

The Chicago CityPASS comes with two options – the C3 and the full CityPASS. With the C3, you can pick three attractions whereas the full CityPASS includes entry to five attractions. The full pass also comes with upgraded experiences like Fast Pass entry to Skydeck at Willis, which I think is a must.

If you have a few days to explore Chicago, I’d definitely go for the full pass.

Book your Chicago CityPASS direct or on Viator

Best Things to Do in Chicago

Now you’re ready to figure out what to fit into your itinerary! From feasting on famous foods and admiring the city from above and below, to museums and visiting the historic Wrigley Field, here are all the things I recommend for first timers visiting Chicago.

We took our tour with Shoreline booked with our Chicago CityPASS (reservations are a must for this activity), but cruises can also be booked as a standalone activity.

Our cruise started from Michigan Ave, which I chose as a closer starting point near our hotel. Shoreline also has cruises boarding at Navy Pier, which is convenient if you already have plans to visit the pier.

For just over an hour, the boat cruises along the Chicago River passing under bridges and floating by the city’s most iconic buildings. Our guide regaled us with punny jokes and gave a lot of information on the buildings as well as the city’s history.

On board, drinks (waters, sodas and alcoholic beverages) and light snacks are available for purchase during the cruise. We snagged some waters and chips to stay hydrated and stave off the hunger until our big lunch at Portillo’s!

What’s the best time of day for an architecture boat tour?

If you’re visiting in the summer, stick with early morning hours or evening when the sun starts to set to shield yourself from the sun. It can get quite warm and humid in the Midwest in the summer! We did the 10 a.m. tour on July 4th weekend and it was already sweltering.

If you want to get a shaded seat, get in line early so that you can snag a good spot when boarding (at the back of the boat or on the lower deck if doing a Shoreline cruise). However, be aware that some of the shady spots will obstruct your view of the buildings. I stood at the back of the boat most of the time so I could get great views behind the boat while still being in the shade.

I do think seeing the city at golden hour or even just after sunset is a great alternative. There’s still daylight and the city starts to light up. I’m absolutely going to book an evening tour next time we’re in the city!

Ticket & Reservation Notes

Even though the 360 Chicago is included in the CityPASS, I ended up booking our tickets separately as we were going to use up our slots with three other activities (the Art Institute, architecture cruise, and the Field Museum). Again, I did price things out individually to pretty much break even on the costs with the CityPASS.

With the CityPASS, you do still need to reserve your 360 time slot ahead of time. If booking separately, buying online in advance saves you the wait time of purchasing tickets onsite. We went with the General Admission since it was an off-peak time (4:30 p.m.) and weren’t too concerned about wait times. However, the CityPASS option does include Fast Pass Entry.

CloudBar Tips

There are different ticket packages available if purchasing direct with 360 Chicago: General Admission, admission with TILT, and admission that comes with a drink (and optional TILT). You are limited to a special drink menu if you purchase a package though.

Where it’s worth it: If you want a cocktail ($23 a piece otherwise!) or glass of wine (starting at $16), the Sip & View package is worth it. However, if you just want a beer, get a GA ticket and purchase a beer separately.

Zero Proof drinks and choices for kiddos are available too, like strawberry lemonade and Shirley Temples.

It was lovely to have a drink at the bar during our 360 experience and be able to linger a bit while enjoying the views from the observation deck. Highly recommend!

TILT Experience

If you’re adventurous, you can add on the TILT Experience, which is essentially a glass box that tilts out of the building, offering views of the city below.

I personally am not into thrills like this, but we watched others do it! Some people chickened out right as it started and others seemed to really enjoy it. The whole experience only lasts a couple of minutes from load time to tilt and finish.

What’s the best time of day for the 360 Experience?

I think the views from 360 would be stunning at any time of day! We went in the late afternoon (4:30 p.m.) on a beautiful, clear summer day and had amazing skyline views, coastline views, and a clear view of Navy Pier.

If you can swing it, time your visit to go up just before sunset to catch the city at Golden Hour and linger with a bevy while the city starts to light up at night. Keep in mind, this time of day is peak – meaning you’ll likely encounter more crowds and a higher ticket price for entry.

Skydeck at Willis Tower

Formerly known at Sears Tower (but really, still known to locals as such), Willis Tower is a legendary Chicago skyscraper. It previously held the title of tallest building in the world from 1973 to 1998, though it’s now relegated to the 26th position. It is still the 3rd tallest building in the United States though!

Ticket & Reservation Notes

We booked our tickets with the Chicago CityPASS, 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 for the Skydeck, especially for when it comes time to standing in line for The Ledge. That line can get pretty long for general admission and wait times can be lengthy, even though there is a time limit in The Ledge.

The Ledge Experience

Aside from city skyline views, The Ledge is the biggest draw at Willis Tower. The Ledge experience consists of several glass boxes that stick out of the building that people can stand in (or sit in – whatever you feel comfortable with).

Not being a big fan of heights, I was hesitant to do this but knew we just had to get in there for the sake of saying we did. My legs were shaking the entire time!

Some things to note about The Ledge:

• If booking with the CityPASS, you’ll get expedited entry for both elevators to the observation deck as well as the line for The Ledge. The fast pass line for The Ledge is worth the expedited entry alone!
• There is a time limit in The Ledge boxes depending on the size of your group (i.e. groups of 3 or less get 60 seconds; groups of 4 get 90 seconds). It is worth noting you can go into The Ledge boxes multiple times – you’ll just have to wait in line each time.
• Professional photos are available if you don’t want to rely on your cell phones/personal cameras. These, of course, are a bit pricey but I do think they are pretty good quality.
• Visit on a weekday for less crowds.

What’s the best time of day for the Skydeck?

Much like the 360 Chicago Experience, I don’t really think there’s a bad time to go up to the Skydeck. However, we did the 7:00 p.m. time slot and were able to catch the sun setting over the city!

The Bean at Millennium Park

The Cloud Gate sculpture, affectionately nicknamed “The Bean,” is one of the most visually-identifying landmarks in Chicago these days. Located in the bustling Millennium Park, it’s on almost every first timer’s bucket list!

The Bean is a really cool piece of artwork and it’s pretty incredible that there are no visual seams despite it being made of 168 stainless steel plates welded together.

Aside from it being a great spot for a photo op, make sure you take the time to walk around the entire sculpture and admire the city’s reflection from all the different angles.

When you’re done at The Bean, if visiting in May through October, head over to Double Clutch Beer Garden at the edge of Millennium Park for a break. It’s a great spot to grab a drink and people watch.

Catch a Cubs Game at Wrigley Field

Established in 1914, Wrigley Field is one of the most historic baseball stadiums in America! It is also the second oldest, just behind Boston’s Fenway Park.

This stadium exudes old baseball charm both in physical appearance and in spirit. The scoreboard is still hand-turned and the marquee sign out front is the same sign (repainted/refurbished throughout the years) that’s been there since 1934.

Even if you aren’t a big baseball fan, a visit to Wrigley Field is a must for a visit to Chicago in my opinion.

We went to a game on the 4th of July and I gotta say, it was one of the best baseball games I’ve ever been to! The stadium was packed with fellow ballgame goers and for the holiday, they had special events like a parade featuring the Budweiser Clydesdales and a jet flyover after the national anthem.

Chicago dog in hand, we watched the Cubs score numerous home runs to rile up the crowd. I’ve never felt more patriotic than watching people come together to enjoy an American pastime while celebrating the birthday of our country.

Tips for Visiting Wrigley Field

Transportation: The easiest way to get to Wrigley is to take the L Train from a downtown station and get off at Addison. You’ll know you’re going in the right direction when you start spotting other baseball fans in transit.

Make time for Wrigleyville either before or after the game. Wrigleyville is the neighborhood surrounding Wrigley Field essentially dedicated to baseball fans with shops, bars, and restaurants. We arrived a couple hours before the game and hit up Do-Rite Donuts for breakfast and found a bar to have a drink and watch the festivities below.

Beware of “Charity” Photographers: We encountered guys at the front of the stadium being quite aggressive about taking your photos with your own phone. Just ignore them and go on taking your selfies or find a nice family to help you instead. These guys are out there hustling to make money by doing you this “favor” and then demanding a tip.

Navy Pier

Navy Pier is a popular destination for visitors to Chicago with tons of foodie spots, shops, games and rides, and is a docking location for Lake Michigan and Chicago River boat tours.

We visited Navy Pier in the summer to check out the views of the city and lake and try some of Chicago’s iconic eats. One of my favorite Italian beef sandwiches was had at Chef Ciccio, and AB&D is dishing out decent Chicago dogs.

And don’t forget to pick up an Original Rainbow Cone for a cool ice cream treat to beat the heat!

Navy Pier also hosts summer fireworks shows from the end of May through Labor Day every Wednesday at 9:00 p.m. and Saturday at 10:00 p.m. Of course, this is a prime location for fireworks watching but you could also go up to the 360 deck in John Hancock Tower at night for incredible city views along with the fireworks!

Best Things to Do at Navy Pier

• Rides and games, including Flyover Chicago and the Centennial Wheel
• Architecture boat tour
• Shopping and restaurant hopping
• Summer fireworks from end of May through Labor Day on Wednesdays at 9:00 p.m. and Saturdays at 10:00 a.m. (weather permitting)

Art Institute of Chicago

if you’re an art lover (or even a Ferris Bueller fan), you’re going to want to wander through the Art Institute of Chicago, which houses countless works from numerous centuries.

For me, I came to see one very specific piece and the rest were a bonus: A Sunday Afternoon on the Island of La Grande Jatte by George Seurat. For years, this has been one of my favorite paintings and I always find it so relaxing to look at (so much so that I have a print in my house). If you’ve seen the film Ferris Bueller’s Day Off, you might recognize this one!

I did also particularly enjoy the medieval armor exhibit showcasing swords and other weapons and body armor from that period. There are also Van Goghs, Monets, Picassos, and another highly recognizable painting called American Gothic. This museum is huge and you’ll definitely want to dedicate a few hours to explore.

Tickets & Entry

• We used our Chicago CityPASS for entry into the Art Institute and no reservations were required, even on a bustling 4th of July weekend.
• You can also purchase tickets at the museum in person, or book ahead online.
• Take note of the museum’s hours on the day you want to visit and keep in mind it is closed on Tuesdays.

Stroll Along the Riverwalk

The Riverwalk is a 1.25-mile stretch of pedestrian area located on the south bank of the Chicago River. Lined with cafes, restaurants, and boat docks, this is the best spot to spend a warm summer night in the city!

My pick: stroll down to The Northman Cider & Beer Garden to grab a bite to eat with a pint of beer or cider. There are picnic-style tables and benches set up under string lights, making is the perfect spot to relax and watch boats float by while admiring the city’s twinkling lights.

Make a Harry Potter Chicago Pit Stop

While this isn’t a quintessential Chicago thing, this Harry Potter store in the Magnificent Mile neighborhood is huge and such a fun stop for all Harry Potter fans (even for the big kids like me)! I didn’t even realize it existed until we passed by on our way back from dinner at Gino’s East and I had to make an immediate detour.

Along with shopping opportunities galore, Harry Potter Chicago also has a Butterbeer Bar, drawing on inspiration from the Chicago speakeasy scene, serving Butterbeer and Butterscotch Popcorn.

Harry Potter nostalgia will be unlocked right here in the Windy City.

Visit the Field Museum

I’m not typically a big history museum fan, but a natural history museum – sign me up! The Field Museum has over 40 million artifacts (not all on display at the same time) from Native American artifacts and animal specimens from around the world, to dinosaur fossils and relics from ancient Egypt.

We spent about 3.5 hours here and I still feel like we rushed through some parts!

My favorite section of the museum was definitely the dinosaur fossils, including Sue – one of the largest T-rex fossils discovered in the world (and the most photographed artifact in the museum).

I was also fascinated by all the different species of animals on display (especially the birds), though it did make me wonder about how they were all collected…

Tickets & Reservations

We used our Chicago CityPASS for entry and no reservations were required. You can also book tickets ahead online or upon entry to the museum in person.

There is a cafe onsite if you’re looking to get a snack or light meal. They do also have drinks available, including alcohol. Wandering around a museum can get overstimulating and a small break is needed!

And there’s more!

If you’re traveling with kids, you might shift your focus to a few other family-friendly activities. Some additional things you can do on a first visit to Chicago include the Shedd Aquarium (included in the CityPASS) and the Adler Planetarium, next to the aquarium.

Are you a baseball super fan? The Chicago White Sox stadium might be on your bucket list too (though I would definitely say to prioritize Wrigley Field).

Feeling a little overwhelmed? Consider a comprehensive tour of the city where someone does the planning for you and you can just kick back, relax, and enjoy:

• Take a Chicago food tour to sample some of the city’s famous foods
• Get the lay of the city from history to architecture (plus food!) with this all-encompassing downtown Chicago tour

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Chicago is a lively and beautiful city and there’s so much to see on a first-time visit. What will you be adding to your itinerary from this list?