Chicago is my second favorite city in the US after New York City. It has a similar vibe to NYC with lots of skyscrapers, but it has wider sidewalks and you don’t see as many people on the street. If it wasn’t for the long and harsh winters I would consider living there. One of my good friends lives in Chicago, so I visited a bunch of times and I’m familiar with the city. This Chicago 4 day itinerary has everything you need to know to plan your visit to the windy city. This post contains affiliate links. When you make a purchase I may get a small commission at no extra cost to you. Find out more here.
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Chicago itinerary: Day 1
Grant Park
I love Chicago’s parks. They are big, have a lot of green space, and are surrounded by skyscrapers. Grant Park is one of the most iconic parks in downtown Chicago and the perfect place to start your 4-day Chicago itinerary. It’s such a big park that it includes other parks haha. No, I’m not kidding. Millennium Park and Maggie Daley Park are part of Grant Park.
Besides the parks, it has a lot of other attractions, such as museums, fountains, and the iconic Bean sculpture. There are a lot of things to do in Grant Park, so you should spend at least half a day in this area.
If you visit in August, you can also go to Lollapalooza, a four-day live music festival where you can see famous artists, held every year in Grant Park.
Millennium Park
The northwestern side of the park is Millennium Park, where the iconic Cloud Gate sculpture (or The Bean) is located. You can’t say you visited Chicago if you didn’t stop by The Bean, looked at your reflection and tried to snap a Bean selfie.
Buckingham Fountain
Besides the many parks within Grant Park, you can also find Buckingham Fountain here, located in the center of the park. It’s an impressive fountain and the perfect spot to snap a picture.
Agora Big Feet
My favorite section of Grant Park is the Agora Big Feet. It’s a set of 106 big sculptures of legs located at the south end of the park. I love street art and I really liked these sculptures. It was a gift from the Polish Ministry of Culture.
Museum Campus
The Museum Campus, which consists of Adler Planetarium, Field Museum of National History, and Shedd Aquarium, is also located in Grant Park.
Art Institute of Chicago
The Art Institute of Chicago is also in Grant Park. It’s an art museum that has an impressive collection of American art, and it is also one of the top arts schools in the United States. Definitely worth a visit if you like museums.
Navy Pier
The Navy Pier is one of my favorite spots in Chicago. It’s a long pier by Lake Michigan and it has a Ferris Wheel, shops, restaurants, and many other attractions. You could spend a few hours here and not get bored.
Chicago itinerary: Day 2
Willis Tower (Skydeck Chicago)
Willis Tower, originally named Sears Tower, is a skyscraper in the Loop area in Chicago. For me, this building is the most iconic skyscraper in Chicago. It has those two antennas on top, so it’s always easy for me to recognize it. It used to be the tallest building in the world back in the day.
Skydeck is an observation deck at the top of Willis Tower. It’s the tallest observation deck in the United States, located on the 103rd floor. It has four glass boxes nicknamed “The Ledge” on the 103rd floor, so you can see the street below. If you are scared of heights do not look down.
Chicago Theatre
The Chicago Theatre was built in 1921 and it’s an iconic venue for movies and live entertainment. You can get tickets to see a show there or you can opt for a tour instead where you can learn more about the building’s history.
Magnificent Mile
The Magnificent Mile is Chicago’s most famous shopping area. It’s the equivalent of Fifth Avenue in NYC. You can find a lot of shops, restaurants, and hotels on Magnificent Mile. If you want to do some shopping while you’re in Chicago this is the perfect place for that.
Chicago Riverwalk
I love the fact that Chicago has a walkable path by the river. It’s such a great spot for a stroll in between sightseeing. You can find small parks along the way, as well as cafes, restaurants, and bars. If you like scenic walks you must take a stroll on the Chicago Riverwalk.
If you want to learn more about the stories of Chicago’s gangsters and ghosts, then this walking tour that starts near Chicago Riverwalk might be for you.
Architecture River Cruise
The architecture river cruise is my favorite Chicago activity. You’ll cruise on the river for an hour and a half and can see all of Chicago’s iconic buildings. You can do this during the day or during the evening.
It’s similar to Paris’s Bateaux Mouches, but instead of architecture from a few centuries ago you’ll see skyscrapers. I highly recommend this cruise. It’s a lot of fun and it’s a great way to get familiar with Chicago’s architecture.
Chicago itinerary: Day 3
John Hancock Center (360 Chicago)
This is another iconic Chicago skyscraper. It’s located in the Magnificent Mile area. It is 3 stories shorter than Willis Tower, but it offers a great 360 degree view of the city.
It also has the TILT experience, where you can lean over the edge of the building at a 30 degree angle. There is a restaurant on the 95th floor if you want to dine with a spectacular view of Lake Michigan.
Lincoln Park
Lincoln Park is Chicago’s largest public park. Besides walking trails, there are many other recreational facilities such as soccer fields, basketball courts, baseball courts. There are also two museums and a zoo in the park. There are so many things to do here, it’s worth spending some time exploring this amazing park.
Wrigley Field
Wrigley Field is the baseball stadium that is home to the baseball team Chicago Cubs. If you’re a baseball fan you can catch a game while you’re in Chicago or you can just take a tour of the field.
Chicago itinerary: Day 4
Chicago Botanic Garden
The Chicago Botanic Garden is such a great place! It’s an oasis of peace where you can admire a lot of species of trees and plants. It’s located a bit outside of the city, so you’ll have to drive to get there, but it’s so worth it.
Pro tip: if you visit during the winter holiday period, you will be able to go to Lightscape. Lightscape is an immersive experience with illuminated trails, sound installations, and spots to make s’mores. It’s one of the coolest immersive art installations I’ve been to.
I’ve also been to Lightscape in Brooklyn, but the Chicago one is superior since the Botanic Garden is larger than the Brooklyn one. I highly recommend you check it out.
Milwaukee Mitchell Park Domes Horticulture Conservatory
After spending a few hours at the Botanic Garden, hop back in the car and continue driving to Milwaukee to see the Mitchell Park Domes Horticulture Conservatory. These domes are basically smaller versions of a botanical garden and they also include exotic species of plants. They are not very large, so you can plan on staying there for only 1-2 hours. That way you can drive back to Chicago to eat dinner or fly out.
I’m going to be honest, I would have never gone to Milwaukee if it wasn’t for this day trip from Chicago. I just think that there are a lot of other places that are more appealing to me than Milwaukee (sorry Milwaukee folks!). But I wanted to cross Wisconsin off my list of states I visited, so I decided to do this day trip.
Chicago CityPASS
If you plan on visiting at least 5 attractions in Chicago, then Chicago CityPASS is the best bang for your buck. It includes entry to the Shedd Aquarium, Skydeck Chicago, and 3 other attractions of your choice.
You can choose 3 of the following attractions: an architecture river cruise, Field Museum, 360 Chicago Observation Deck, Museum of Science and Industry, Art Institute of Chicago, and Adler Planetarium. By buying a CityPASS you save 48% compared to buying individual tickets.
What to eat in Chicago
Deep-dish pizza
Deep dish pizza is a traditional Chicago dish and you must try it when you visit. The best places in town for deep dish pizza are Lou Malnati’s, Giordano’s, and Pequod’s. You could try all three or just pick one that’s closest to where you’re staying. They are all good, so you won’t be disappointed.
Now the question is will you like deep dish pizza? Your mileage will vary on this one. Since I’ve lived in NYC for so long, I am a fan of NY pizza. In my opinion deep dish is not really a pizza. You can’t just grab a slice and eat it like you would regular pizza. It feels like it’s more of a pot pie.
The taste is ok, but I’m not a fan of the texture and the fact that you have to cut it with a fork and knife to eat it. I don’t know, it doesn’t do it for me. But don’t let that discourage you. You might love it and you should definitely try it while in Chicago.
Pot pie pizza
While I wasn’t a huge fan of the deep dish pizza, I loved the pot pie pizza. You can get it at Chicago Pizza and Oven Grinder Co. At least this version is called what it actually is: a pot pie. It’s an individual serving pot pie made from scratch.
It’s made with a special tomato sauce, sausage, and mushrooms. When they bring it out it’s actually upside down, so you basically see the dough of the pie on top. And then they turn it upside down so it becomes a bread bowl and you have the melty cheese on top. It’s delicious!
Chicago hot dog
While a NYC hot dog is usually served in a plain bun with your choice of ketchup and/or mustard, a Chicago-style hot dog comes with many more toppings. It’s served on a poppy bun and it is topped with mustard, relish, white onions, tomato slices, a dill pickle spear and pickled peppers.
The NYC version of the hot dog is my winner. For me personally the Chicago hot dog has way too many toppings and it makes eating it a mess. But it’s definitely worth trying it once for the experience.
Stan’s Donuts
Stan’s Donuts is a paradise for donut lovers. They have so many flavors and they are all delicious. The perfect breakfast along with a cup of coffee. I got the biscoff and banana donut and it was 10/10.
Brunch
Brunch is always a good idea, especially when you’re traveling. Yolk is a very popular spot for brunch in Chicago. When I went there with my friends, we had to wait about 20 minutes to be seated. Other popular choices are Batter & Berries and Wake ‘n Bacon.
Dinner
There are plenty of very good restaurants where you can get dinner in Chicago. I recommend Girl & The Goat, Boka, Monteverde Restaurant & Pastificio, and The Purple Pig. If you’re looking for a fancy, 3 star Michelin experience, you should go to Alinea.
Where should I stay in Chicago?
Mid-budget hotels
Chicago has a lot of great mid-budget options for hotels, such as: The Gwen – a Luxury Collection Hotel, Sofitel Chicago Magnificent Mile, and LondonHouse Chicago – Curio Collection by Hilton.
Luxury hotels
If you have a higher budget and are seeking a more luxurious option in the city center, then The Peninsula Chicago, The Langham, and Four Seasons are all great options.
Hostels
Unfortunately, I am not the right person to recommend you any hostels. I am in my 30s and I value comfort, so I will always choose to stay at a hotel vs a hostel. I can see how a hostel is a great option for younger people, but I’m at a different stage in life, so I prefer hotels.
Airbnb
I also tend to pick hotels over Airbnbs because I feel like it’s less of a risk and it’s a more reliable option. One time when I visited Miami with my friends we booked an Airbnb that looked great in pictures but looked really bad in reality. We ended up going to a hotel instead. After that experience I tend to avoid Airbnbs altogether.
Best time to visit Chicago
It’s best to visit Chicago during the warmer months. That way you can spend time outdoors to explore the city. Chicago gets very cold during the winter, and winter lasts about 6 months. This is the main reason why I could never live there. I love visiting the city when it’s warm outside, but enduring the strong winds and cold temperatures every winter is not for me.
How to get cell phone data when visiting from abroad
The cheapest and most convenient way to get data while visiting from abroad is to buy an eSIM. An eSIM is a digital SIM that lets you activate a data plan from a provider without having to use a physical SIM card. They are super easy to use. I use Nomad eSIMs (use code IOAN43TM for 25% off your first purchase).
You can go to their website, select the country you’re traveling to, select how many GB of data you want, and how many days you want the eSIM to be active for. After you pay you will receive a confirmation email with instructions on how to activate the eSIM. You can activate it on your phone and the process takes under 1 minute. Once the eSIM is activated you don’t have to do anything else. When you’re at your destination you will automatically get data.
How to get to the city center from the airport
Train
You can take the L train to get to downtown Chicago from both O’hare and Midway airports. It takes about 45 minutes to get downtown from O’Hare and 25 minutes from Midway. The tickets cost around $5. You can get the tickets from the Ventra card machines at the airport.
Taxi / uber
This is the most convenient option since it leaves you right in front of your hotel. Taxis cost about $40. Ubers cost between $35-50, depending on traffic. Alternatively you can also schedule a private transfer.
Is Chicago safe for a solo female traveler?
Chicago has a bit of a reputation as a not so safe city. I’ve been to Chicago close to 10 times and I always felt safe. As long as you don’t venture into neighborhoods that have a bad reputation and plan on visiting just the central neighborhoods where most tourist attractions are it will be fine.
How can I get around Chicago?
Chicago is a pretty walkable city by US standards. A lot of attractions are a short walk from each other in the downtown area. Chicago also has a great subway system, the Chicago L. Two lines offer 24 hour service. Chicago, along with NYC and Copenhagen are the only 3 cities in the world that have 24 hour subway service for some lines. If you don’t like to take the subway you can always take an uber.
Do I need to book tickets for attractions in advance?
I highly recommend you book all the tickets online in advance of your trip. Chicago is a very popular destination so it’s very likely that tickets will sell out. Especially if you visit during the summer months. Booking in advance will give you peace of mind.
Do you recommend Chicago as a solo destination?
Yes, I recommend Chicago as a destination for solo female travelers. It’s a great city, it offers plenty of things to do, and the food scene is fantastic.
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