Chicago is officially my favorite city in the United States! It’s filled with stunning skyscrapers, fun nightlife, great food, gorgeous views of the Chicago River that runs through the heart of downtown, outgoing people, and lots of activities.
First time in Chicago? No worries, I’ve got ya covered! There are a couple of things you must do like eat Chicago-style pizza, see the iconic “Bean,” take a river cruise tour, and so much more!
Here are my top recommendations of things you can’t miss your first time in Chicago.
Where to Stay
Accommodations in Chicago are VERY expensive.
The best places to stay for first-timers that make it easy to walk to most attractions are:
Chicago Loop
River North
Magnificent Mile
We stayed at the Acme Hotel Company in River North because it was in a great location. It was also the most reasonably priced hotel we could find at the time. The hotel has a cool and funky vibe, and the room was very comfortable. We’d stay there again.
Getting Around
Chicago is an extremely walkable city. We stayed in River North and only had to hire an Uber to get to and from the airport. The rest of the time, we walked to all the attractions listed on this bucket list for first-timers in Chicago. Except for Wrigley Field. We rode on the L train to get to Wrigley Field from downtown.
Public Transportation
The Chicago Transit Authority services the bus system and train lines known as the “L” train lines. The “L” is short for elevated.
As with any big city, there are sketchy neighborhoods and crime. I would try to avoid traveling on the L train late at night if you don’t have to, IMHO. There are always people riding the L train at all hours of the day, but obviously, the daytime will be safer.
Full disclosure: my husband and I saw a guy get punched in the face multiple times when we were trying to purchase our train passes. We were also approached by a guy asking for money. When we said we didn’t have cash, he insisted that we use the ATM that was near us.
If you’re like me, and this type of public transportation stresses you out (I realize some people have gotten used to this type of stuff and it isn’t a big deal to them), have someone with you. That way, you don’t feel so vulnerable, or try to avoid it altogether. Because sometimes you do come across shady people and strange situations. At least that’s been my experience in big cities.
Aside from those few scenarios, the L train routes were easy to figure out. It was also super easy to purchase the train passes from the vending machines.
Bike/Walk
There are many bike lanes and sidewalks in the city. Most people walk a lot or ride their bikes.
My husband and I noticed that cars don’t like to stop when pedestrians walk on crosswalks. We had to dodge out of their way sometimes, even when we had the green light to walk. We even talked to some locals about this, and it seems to be a common occurrence in the city. Many of them have been hit by a car when they were either walking or on their bike. Not just once… multiple times.
Just be mindful of cars as you walk and look up at the architecture or when you’re looking down at your phone for directions.
Uber/Lyft
Very easy to use this kind of transportation in the city and it’s my preferred method of traveling, if I can’t walk somewhere. Just keep in mind that prices increase during times of high demand.
Car Rental
Not worth it in Chicago, in my opinion, unless you plan on taking day trips outside the city.
Best Time to Visit
Summer (June-August): Summer is the peak season in Chicago. Accommodation prices will be at their highest. The weather is hot, but it’s the best time for hanging out at the beach and doing outdoor activities.
Fall (September-October): Cooler weather and fewer people. During our trip, It was warm during the day, but we needed a sweater/hoodie in the mornings and evenings.
Winter (November-March): Extreme cold and snow. If you’re brave enough, you will find some of the lowest hotel rates during this time. Just bring your warmest layers!!
Although the Fall weather (end of September and first week of October) was amazing because I love sweater weather, I’m eager to return to Chicago in the summer! All the locals rave about how the city comes the most alive with the great weather.
Cruise Down the Chicago River
My #1 recommendation for fun things to do in Chicago is to take an Architectural Boat Tour on the Chicago River. It’s the best way to see and learn about Chicago’s most iconic and historic buildings. You can’t visit Chicago and not get on the water!
This activity was the highlight of the trip, hands down.
There are many boat tours for you to choose from, but we went with Chicago’s First Lady Cruises. There wasn’t a bad seat in the house, the tour guide was very knowledgeable, and the views were phenomenal!
Pro tip: If you are visiting during the colder months, it can get REALLY cold up on the deck, so bundle up!
Address: 112 E Wacker Dr, Chicago, IL 60601
Visit an Observation Deck
Head to Skydeck Chicago for some of the best panoramic views of Chicago from the 103rd floor in the Willis Tower!
It’s a great place to see views over the city. You can also step out on The Ledge, a glass box/balcony that extends four feet outside of the Willis Tower. It’s pretty epic and a fun thing to do in Chicago.
There is a lot of debate over which is the best observation deck in Chicago. Skydeck Chicago or 360 Chicago. They each have pros and cons, but after visiting both, I recommend Skydeck Chicago over 360 Chicago!
You could also do as we did and visit both. Maybe one during the day and the other at night? But if you only have time or budget for one, I would skip 360 Chicago and check out Skydeck instead.
Pro tip: Arrive early when it’s not crowded. The amount of time you can spend on The Ledge is limited and timed by the staff so that everyone gets a fair chance on The Ledge. However, if there isn’t a wait to take pictures, they let you be there longer.
Address: 233 S Wacker Dr, Chicago, IL 60606
Walk Through the Parks
Chicago is known for its many lush green areas and public art. Grant Park’s main features are Buckingham Fountain and Millennium Park.
Millennium Park is where you will find the famous Cloud Gate (the bean) and Crown Fountain.
The most iconic sculpture in Chicago is called Cloud Gate, but it’s more commonly known as The Bean. (Let’s be honest, the shape does look like a bean!)
Yes, it’s touristy and always crowded, but you can’t visit Chicago for the first time and NOT take a fun picture at The Bean!
After you have your picture, walk to the nearby Crown Fountain to see another well-known public art installation in Chicago.
Buckingham Fountain is another famous landmark in Chicago that is easy to walk to from either Cloud Gate or Crown Fountain. It’s one of the largest fountains in the world! I also know it from the intro to the show Married with Children!
Want to walk and explore a bit more? Then head across the street toward the water to walk or bike the Lakefront Trail, a path that follows Lake Michigan’s shoreline.
Address to Cloud Gate: 201 E Randolph St, Chicago, IL 60602
Try Deep-Dish Pizza
Chicago is famous for its deep-dish pizza, so trying it for the first time was high on our list of fun things to do while visiting Chicago. Hey, eating counts as a full-on activity in my book.
I’ve always heard the debates as to which is the better pizza, Chicago’s deep dish versus New York style pizza, and now after having both, my favorite is still New York pizza. They are both tasty, but nothing beats NY pizza.
We tried deep-dish pizzas at the two most famous places, Giordano’s and Lou Malnati’s. My husband and I agreed that Giordano’s was better for the best deep-dish pizza.
We ordered the small pie, and it was enough for the two of us. The slices are very filling! The deep-dish pizza has a high, thick crust, maybe about 1 inch deep, and has a generous amount of tomato sauce and cheese (plus various additional toppings). Because of its thickness, it does take longer to cook.
Tip: Deep dish pizza takes about 45mins to come out, so try not to go when you’re starving and hAngry. If you absolutely must have something to eat, have a VERY light salad while you wait for the pizza.
Address: various Giordano’s locations
What to order: deep-dish pizza with your favorite toppings!
Have Drinks on a Rooftop
Checking out the views of the city from a rooftop is a must on my list. Having a yummy drink in hand while on a rooftop in Chicago, well, that’s just a fun bonus!
My favorite rooftop to grab a drink is the LondonHouse Rooftop. I recommend going to LH Rooftop to watch the sunset because it is so magical. The views of the Chicago river, the skyline, and all the magnificent buildings are stunning.
LondonHouse rooftop
Address: 85 E Wacker DR 22ND Floor, Chicago IL 60601
What to order: guava margarita
Another great restaurant with amazing views is Cindy’s Rooftop. It has stunning views of The Bean and other landmarks in Millennium Park. We also tried some items from their brunch menu, and they did not disappoint. I always worry that places with amazing views are overpriced solely because of their location and not because the food is good. I was pleasantly surprised at all the yummy dishes!
Cindy’s Rooftop
Address: 12 S Michigan Ave, Chicago, IL 60603
What to order: Chilaquiles, Buttermilk Pancakes, and the “Not so Secret” Secret Burger
Pro Tip: These popular rooftops book up quickly! Try to make reservations as early as possible. If not, you can always walk in and try to snag a good seat.
See the Cubs Play
My husband is a huge baseball fan, so we visited Wrigley Field TWICE during our trip! The first time we visited Wrigley Field was on a non-game day to tour the stadium and go to spots that aren’t accessible to visitors, like the dugout and the press box. We even got to step out on the field!
The tour was so much fun, we learned a lot, and we experienced the stadium without the crowds, which felt serene and magical!
During our second visit, we were lucky enough to catch the Chicago Cubs playing and watched them win the game.
I recommend that you visit this incredible baseball stadium. This stadium will make anyone a cubs fan!
Address: 1060 W Addison St, Chicago, IL 60613
Go Shopping on The Magnificent Mile
If shopping or window shopping interests you, taking a stroll on The Magnificent Mile is perfect for doing just that. The Mag Mile, as some call it, is a 0.8-mile upscale section of Michigan Avenue in downtown Chicago.
I won’t lie; most of the stores along The Magnificent Mile are pretty expensive. There are a few stores that are not high-end, but I wish they had local shops or boutiques; something different than what I would find at home in Texas.
The highlight for us was walking around the area to check out the sights and impressive buildings; like the iconic Wrigley Building skyscraper pictured above. :)
Address: Michigan Avenue
Take a Stroll through The Riverwalk
The Chicago Riverwalk is a nice 1.25-mile-long path that many people use for running or taking a stroll along the water.
There is also: a winery, cafe, restaurants, and bars lined up along the Riverwalk. You can grab food or drinks while enjoying the gorgeous views and atmosphere.
The Riverwalk is where you find guided boat tours and kayak rentals, in case you’re looking for fun outdoor activities in Chicago.
Address: Riverwalk, Chicago, IL 60601 – There are several entrances to Chicago Riverwalk
Go to the Beach & Navy Pier
Even if you aren’t visiting during the warm months, you can still spend a fun day seeing a beach in the middle of downtown Chicago. You may still catch people sunbathing or playing fetch in the water with their dogs. The views of the water against the city’s beautiful skyline are breathtaking!
If you don’t mind doing something a bit touristy, walk over to Navy Pier for more awesome water views. I wouldn’t go out of my way to drive there and pay for parking and the attractions, though. To ride the Ferris wheel, one of the main attractions of the Navy Pier, will cost you $15-$18 per person, depending on the age. But there is no admission fee to enter and walk around.
If you have children and are looking for ways to keep them busy, this is a fun place to take them.
On our last day in Chicago, we wanted to go at a slow pace and explore, so we walked to Ohio Street Beach.
From there, we continued walking to the Navy Pier. We took our time and walked to the pier and just enjoyed the peaceful water and stared at the boats passing by or at the lighthouse seen at a distance.
OHIO STREET BEACH
Address: 600 N Lake Shore Dr., Chicago, IL 60611
Navy Pier
Address: 600 E Grand Ave, Chicago, IL 60611
Catch a Concert or Broadway Show
There are numerous theatres and concert venues in Chicago, which makes it a great place to catch many fun Broadway shows, musical acts, and comedy performances.
Our trip coincided with the opening week of the Broadway show Wicked. We hadn’t planned on doing this, but we stumbled upon it as we walked through the Chicago Theater District and saw posters of the show at Chicago’s James M. Nederlander Theatre (that’s the beauty of leaving some space in your trip to do something spontaneous). We were so glad we got to experience Broadway in Chicago; it was one of the best shows ever!
Hopefully, you’ll plan on catching a fun show while you’re in Chicago. Or better yet, hopefully, you haven’t planned out every second on your itinerary and have left time open for impromptu experiences!
Address: Chicago Theatre District – 2 W. Randolph St., Chicago IL 60602
Other Places to Eat in Chicago
Breakfast & Coffee:
- Yolk – The Red Velvet French Toast is amazing.
- Stan’s Donuts – The Biscoff Pocket was my favorite!
- Foxtrot – The Pumpkin Pie Latte was the perfect fall drink!
- Goddess and the Baker – The Strawberry Matcha and Honey Wildflower Lattes were delicious.
Lunch & Dinner:
- Portillo’s– Known for Chicago-style hotdogs. Pair it with the chocolate cake shake!
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