chicago itinerary

The “Bean” (c) ABR 2014

Chicago has to be one of the most exciting and culture-rich cities in the United States. It is also likely to be one of the most well-known Midwest cities. As such, Chicago is a great place for both domestic and international travelers. If I am being honest, the nature enthusiasts out there might find that there is something left to be desired (although I have it on good authority that there is some good hiking just outside of the city at Starved Rock State Park and Waterfall Glen). But almost any other traveler preferences can be found in the city. People watchers will likely find no where better in the US, besides NYC. Shoppers can find everything from big, brand names to small businesses with finds that you can get no where else. Selfie pros and adrenaline junkies will enjoy the views of the tall buildings that welcome visitors, and fishers and boaters will of course be entertained by one of the largest lakes in the world. In short, if you are considering Chicago, the city likely has something to offer you. This guide will help you design your perfect Chicago itinerary.


There are TONS of museums in Chicago, many of which are world class. No matter your interests, I would highly suggest visiting at least one of the city’s museums. If you want to my absolute favorites, you can check out the Shedd Aquarium, Field Museum, and Adler Planetarium all in one beautiful, lake-side complex.

chicago itinerary

The Field Museum (c) ABR 2014

The Field Museum is highly immersive, which is my favorite kind of museum. You can waltz yourself through past versions of the Earth, learn about the history of Chicago and the many cultures of the planet, while also visiting grand rooms showcasing models and skeletons of some of the world’s most fantastic, inspiring animals. Whatever you are learning about, however, you will often find yourself feeling transported and surrounding by the different themes of the halls.

chicago itinerary

The Shedd Aquarium (c) ABR 2014

The Shedd Aquarium caters to anyone interested in learning more about and enjoying the marine world. A basic ticket will get you in to see all kinds of beautiful fish from around the planet. The place is so big it’s easy to get lost in wonder as you wander its halls, and there are plenty of ticket additions if you want to see more. There are also special exhibits, movies, and even small cetacean shows.

These two amazing museums are also really close to eachother, making them the perfect day trip, particularly when coupled with the Adler Planetarium. After all that, if you still have energy, you can also explore Northerly Island for some perfect views of Lake Michigan.

Museum Info

chicago itinerary

(c) ABR 2014

Here is a short list of the top museums in the city for you to consider for your Chicago itinerary.

(1) The Field Museum: Natural and Human History
1400 S Lake Shore Dr, Chicago, IL 60605
Open seven days a week 9am-5pm
Ticket information: All-access: Adults $38, Basic Access: Adults $24
All ticket types have options for children (3-11), seniors (65+), and students with IDs.

(2) Shedd Aquarium
1200 S Lake Shore Dr, Chicago, IL 60605
Open seven days a week from 9am-6pm
Ticket information: General admission for adults is $39.95, with options for children and Chicago residents.

(3) Adler Planetarium
1300 S Lake Shore Dr, Chicago, IL 60605
Open seven days a week from 9am-6pm
Ticket information: All-access: Adult $34.95, General admission: $12
With ticket options for children (3-11)

(4) The Art Institute of Chicago
111 S Michigan Ave, Chicago, IL 60603
Open seven days a week 10:30am-5:00pm
Ticket information: General admission: $25 for adults with options for Chicago and Illinois residents, as well as teens (14-17), students, and seniors (65+). Kids get to come in for free!

(5) Museum of Contemporary Art Chicago
220 E Chicago Ave, Chicago, IL 60611
Monday: Closed
Tuesday: 10am-9am
Wednesday-Thursday: 10am-5pm
Friday: 10am-9pm
Saturday-Sunday: 10am-5pm
Ticket information: General admissions is $15 for adults, with options for students, teachers, seniors and IL residents.


chicago itinerary

(c) ABR 2014

The Magnificent Mile is a great place to go if you are looking for the high-end Chicago experience. Not only will you be able to shop and eat in style, but many of the city landmarks are easily accessible from this area. It’s a great place to start if you want to spend some time walking the city and packing in all the main sights.

If you have the time to explore a bit more, be sure to consider some other parts of the city for your Chicago itinerary, however.

chicago itinerary

Chicago Chinatown (c) ABR 2019

Chicago’s Chinatown isn’t particularly big or flashy, but it’s easily accessible by train and there is some absolutely AMAZING food to be had here. Our recent favorite is Strings Ramen at 2141 S Archer Ave, Chicago, IL 60616, right near the heart of the area. In between delicious meals from around the Asian continent, the street is lined with shops full of just about anything you could want for a souvenir.

chicago itinerary

Spicy ramen (c) ABR 2019

Boystown is another one of my favorite areas of the city for shopping, particularly at smaller businesses. For LGBTQ+ travelers and allies, this area of Chicago is also a great place for history, nightlife, and it hosts an amazingly vibrant Pride Parade every year as well.

Adrenaline and Views of the City

chicago itinerary

(c) ABR 2014

For the adrenaline junkies among you the Skydeck Ledge and 360 Chicago are two must-haves for your Chicago itinerary. The Skydeck Ledge is a little subsection of the upper floor of the Willis Tower (formerly the Sears Tower). For this one, you get to stand out over the city in a transparent, three sided box. It’s the kind of thing that puts me on edge (lol), because I really don’t like seeing my feet floating high, high up in the air by any account. This isn’t something that you have to do, however. If you just want to take pictures, you can stay on solid ground and capture some great views of the city. General admission is $25 for adults.

chicago itinerary

(c) ABR 2014

The other option is the 360 Chicago Observation Deck which is in the John Hancock Building. You can go up there to just get great pictures of Lake Michigan and the city (they are also open at night). But they have their own adrenaline fix called the Tilt. This is a glass wall that will slowly tilt you out over the city for the experience of being leaned out over a huge drop. Tickets are $22 for adults during the day and $26.50 at night. For the Tilt you will need to pay an extra $8, but you cannot get a reservation ahead of time.

Navy Pier and Wrigley Field

I’ve been to Navy Pier only a couple times over the course of the many years that I have visited Chicago, and while I think it isn’t really worth a repeat visit, it is a great stop for your Chicago itinerary if you enjoy rides, carnival food, or just want to walk out over the water. If anything, riding the Centennial Wheel is a great way to spend time with friends and get more great pictures of the city.

Another major landmark in Chicago is Wrigley Field. Whether you are a baseball fan or not, if you have the chance to visit, do it. There is so much history here, and going to a game at Wrigley will be like no where else.


chicago itinerary

City streets (c) ABR 2014

Parking in Chicago can honestly be a nightmare, particularly if you are in the heart of the city. Being good at parallel parking will come in handy, but you will also need to budget for parking if you bring a car, because basically all parking is paid.

For more info on garages and meters and have good information to help you plan.

Alternatively, Chicago has a great train system, so you can avoid driving and parking downtown altogether. All you need to know about this can be found here:

Where to Stay

chicago itinerary

(c) ABR 2014

There are tons of places to stay in Chicago, and if you are planning on spending lots of time downtown, you can save some money by lodging elsewhere and then taking the train into town. However, be sure to read reviews for anywhere that you stay carefully. There are some areas of Chicago that are not safe for visitors. Don’t risk your safety to save a few bucks.

If you do want to stay downtown and have some extra cash, I would suggest checking out the Drake. The rooms are lovely and you are right in the center of the city’s action when you stay there. It is a little sad that this is just a franchise hotel now, but it’s still a historic site and a great experience.

Where to Eat

chicago itinerary

Chicago hotdog (c) ABR 2019

Pretty much anywhere with good reviews. Chicago has something for everyone in terms of food. Definitely give a Chicago hotdog a try with all the toppings at least once. When looking for a good place to get these, pick smaller restaurants. In particular, the ones with no seating appear to be the best.

Deep dish pizza is another must try, and there are some great options downtown. Finally, there is an Italian restaurant that my whole family loves called Orso’s. The food is amazing and the story behind it is so quintessentially Chicago that it’s well worth the journey out of downtown.

Should You Consider the CityPass?

Based on the prices above, what you want to see, and how long you will be in the city should determine whether or not the CityPass is worth it for you. I personally think it is good for people visiting the city for the first time, and who want to pack a lot into their itinerary.

Generally speaking, the CityPass is $108 for adults and $89 for children (3-11) and it will work for a 9-day period. Basically, if you are going to visit more than 2 or 3 of the attractions in the following list, it is likely worth while. In many cases you will get to use a shorter line as well, which is a nice perk.

CityPASS Admission Includes

  • Shedd Aquarium – Priority Entry
  • Skydeck Chicago – Day/Night Admission
  • Field Museum – All-Access Pass
  • Adler Planetarium – Premium Pass   OR   Art Institute of Chicago – Fast Pass
  • Museum of Science and Industry – Entry +1 Ticketed Experience   OR   360 CHICAGO Observation Deck – Express Entry

Safety Considerations

chicago itinerary

(c) ABR 2014

When it comes to safety in Chicago, I think being very respectful, staying aware of your surroundings, and staying out of bad neighborhoods will go a long way. I am not enough of an expert to tell you exactly where not to go, but if you stick to these tourist spots, you will likely be fine. If you need more information, check out this post on the safest and most dangerous neighborhoods in the city.

As always, remember that your safety is always your own responsibility. Be smart, and learn more before you go. Let friends and family know your plans.

Learn More About Illinois

If you want to learn more about exploring Illinois and get inspired for your next trip, be sure to look at our Guide to Illinois.

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