Last Updated on 01/02/21 by quiltripping
Frank Sinatra said it best when he sang “My Kind of town Chicago is”. If you are planning a first trip to Chicago, there are a wide range of sights and activities to choose from. Here is a list of my 25 top things to do on a Chicago 4 day itinerary (though I suggest spending more time in my favorite city if you can).
I grew up in Chicago and spent my formative years there. Even though I have been away for half my life now, I still think of it as home and go back to visit a few times each year. There is always plenty for me to do and see on my visits, whether it’s going back to some of my favorite sights or trying something new.
For the visitor, Chicago is an easy destination to tour. You can easily get from the airport to the downtown “Loop” area on inexpensive public transportation and then many of the most popular attractions are within walking distance.
How to get from the Chicago airport to downtown
Chicago’s O’Hare airport (ORD) is about a 30 minute drive from downtown under good traffic conditions on I-90 (which isn’t often). You can take a taxi or a ride-share vehicle, but it is just as easy to take the train from the airport into the city. The blue line train terminus is at O’Hare Airport. Just follow the well marked signs to get from baggage claim to the station. You can buy a one way ticket at one of the kiosks or if you have a tap-and-pay credit card, just use that to go through the turnstiles.
Chicago’s blue line has undergone a recent multi million dollar renovation, which means the stops along the route are clean, well lit and accessible. Depending on where you are staying downtown, you may want to change trains at the Clark/Lake or State/Lake stops to one of the other lines if you do not want to walk a few extra blocks.
If you are flying into Chicago’s Midway Airport, then take the orange line into downtown which terminates at this airport. Use this handy CTA map to help you navigate.
Where to stay in Chicago
Chicago has a dizzying array of accommodation options, especially in the downtown area. The choice depends on your budget, the types of services you want from a hotel, how much space you need and the location. There are historic options like the Drake Hotel (where I have stayed a few times), the Palmer House or the Blackstone. There are also many new high end choices as well as the many less expensive chain hotels. It really all comes down to your own personal preferences.
I suggest staying in the downtown-loop area so that you do not have to spend as much time in transit. If the majority of the activities you want to do are along the lakeshore, then I recommend staying within walking distance. It’s about a 3 mile walk from the north end of downtown at Oak Street to the Adler Planetarium on the south end museum campus. Staying at a hotel near the Chicago River or Millennium Park will put you midway and will make it easy to walk to the majority of the sights of interest.
How long should you stay in Chicago
Ideally, I would recommend staying in Chicago no less than 4 days, though if you can stay longer that would be better. There are no lack of things to do and see. The museums are world class and deserve at least a half day each. You’ll want to also stroll the Magnificent Mile and explore Navy Pier, look out over the city from one of the signature skyscrapers, take in a show and have a few good meals.
With 4 days you can explore the heart of the city and enjoy it at a leisurely pace. To see some of the sights beyond the downtown area, like the Frank Lloyd Wright studio and houses, Wrigley Field or the Museum of Science and Industry, you will most likely want to have more time. I recently spent a week in Chicago playing tourist, and did not get to do everything on this list.
Ideas for a Chicago 4 day itinerary in the Downtown-Loop area
My list of 25 Chicago activities includes many of the most popular and “must-see” sights, as well as some of the ones that I think make Chicago unique. Narrowing down this list to just 25 was a challenge. You will want to pick and choose what you want to do based on your interests, budget and the amount of time you have.
Escape our planetary confines for a little while as you explore the universe in the US’ s first planetarium which was built in 1930. The Adler Planetarium is one of the three museums that make up the Museum Campus and offers a wide selection of shows, including one with Big Bird and Elmo for the littlest family members. There are also many great exhibits that span all aspects of star gazing and exploration. Growing up, seeing a star show here on a school field trip was one of my most memorable museum experiences.
Buddy Guy’s Legends Bar
Chicago Blues music had a big influence on the evolution of early Rock and Roll. One of the easiest and most pleasant ways to experience Chicago Blues music is to spend an evening at Buddy Guy’s Legends Bar in the South Loop. You can enjoy acoustic performances during lunch and dinner for free, or, for a small fee, stay after dinner to watch the nightly show.
Chicago Art Institute
At the Chicago Art Institute you will find a world class collection that spans 5000 years of human creativity. If you love impressionism, plan to spend quite a bit of time here studying the many works by Monet, Cezanne, Renoir, Van Goh and others. Go early or just before closing to avoid the crowds.
Chicago Cultural Center
Across the street from the Cloud Gate sculpture is another historic Chicago building, the Chicago Cultural Center. Stop in and take a peek at the world’s largest Tiffany stained glass dome and at all the beautiful inlaid marble surrounding it. The Cultural Center also offers many free performances all throughout the year.
Chicago River Architecture Tour
Chicago is known for its photogenic lakefront skyline and unique and diverse architecture. The 1871 Great Chicago Fire laid waste to most of the city which then created an opportunity for creative new buildings to rise up out of the ashes. Experimentation and innovation became the standard and resulted in some of the world’s tallest buildings at the end of the 19th century.
One of the best ways to see Chicago’s unique and diverse historic architecture is on a Chicago River architecture boat tour. There are many to choose from but I like the one offered by the Chicago Architecture Foundation aboard the Chicago First Lady. You’ll get a fun and in depth commentary of the history of the many buildings, both old and new, as you cruise up and down the Chicago river.
Another cruise that I really enjoyed was the combination river and lake cruise offered by Wendella. I chose an early evening cruise in the summer and watched the sun set over the city as we cruised through the locks and onto Lake Michigan. On the way back, I got to see the beautiful Chicago skyline all lit up at dusk.
Chicago style pizza
Chicago pizza is a true pie – deep and loaded with sauce, cheese and other goodies. There are two types of Chicago pizza: deep dish and stuffed. The deep dish is the most common and is made like an open topped pie. There are a number of good Chicago style pizzeria’s in the downtown area, though you can’t go wrong with the original Pizzeria Uno where deep dish pizza was invented, or its sister spot, Pizzeria Due.
The less common but equally delicious Chicago original is the stuffed pizza. This starts with a layer of dough, then lots of mozzarella cheese which is topped with another layer of dough. Then the sauce and other toppings are added. Giordano’s is one of my favorites for stuffed pizza and there are a number of locations within the Chicago Loop.
There is the historic Chicago Theater building and then there is also the wonderful Chicago theater scene which I think is on par with Broadway in New York city (I’ve experienced both).
The Chicago Theater was built in 1921 for 4 million dollars as the first lavish movie theater of its kind. The interior details were inspired by the Royal Chapel at Versailles and the Paris Opera House. In 1985 the theater was saved from demolition and was fully restored to its original grandeur. Today you can attend performances by top name artists, or you can take a tour to learn all about the history and architecture of this beautiful venue (or why not do both).
For other performance options, Chicago has something for all tastes and budgets (discover what’s playing at Chicago-Theater.com). In the heart of downtown, the Chicago Theater District offers the best of Broadway productions in some of the country’s most historic theaters, but without the New York prices. When Hamilton was playing in Chicago, I was able to get last minute tickets at a fraction of the cost of a seat in New York. You can also tour the best historic theaters to learn more about these beautiful buildings from the early part of the 20th century.
Field Museum of Natural History
The Field Museum is one of the three museums in the south Loop’s Museum Campus. As one of the largest natural history museums in the world, you will find plenty of material for all interests. There are instructive dioramas, Egyptian mummies and lots of pretty samples of interesting rocks. And, of course, there are also dinosaurs – in fact, you’ll be able to see the largest skeleton of a T. rex ever discovered (named Sue).
It’s fun to stroll and window shop on Chicago’s Magnificent Mile which really is a mile long and extends along Michigan Avenue from Oak Street on the north to the Chicago River on the south. The avenue is lined with high end shops like Tiffany, Cartier and Dolce and Gabanna. You’ll also find high end accommodations like the Ritz, the Four Seasons and the Peninsula hotels.
There are also some historic landmarks along this mile with the Chicago Water Tower being one of the most important. It was built just two years before the Great Chicago Fire and is one of the few buildings that survived the devastation. Today the Water Tower is used as an art gallery that showcases the works of local photographers and artists.
My favorite time of year to walk down Michigan Avenue is during the Christmas holiday season. Over a million lights decorate the trees that line the street and the shop windows are colorfully decorated for the holidays.
Marshall Fields (now Macy’s)
The 13 story flagship store for Marshall Field and Co. was built in the early 1900’s, takes up a whole city block and is still the third largest store in the world. Among the architectural details of this historic landmark is a shopping atrium topped by a 6000 square foot vaulted glass dome mosaic made by Louis Comfort Tiffany using 1.6 million pieces of iridescent glass.
Besides its large size, the store also established many shopping “firsts” that we now take for granted: the first store to use escalators, the first to set up a bridal registry and also the first to provide revolving credit. It was also the first to establish a department store tea room which still exists today as the Walnut Room restaurant. This is a good spot for an affordable lunch in historic surroundings, especially at Christmas when the traditional 45 foot tree decorates the restaurant.
Before you leave, make sure to buy a box of Frango Mints-a Marshall Fields classic since 1929.
Millennium Park and its Cloud Gate (aka The Bean) sculpture have become one of the most popular sights in Chicago. The photogenic reflective metal art piece is a big draw for selfie photos, but the park also offers other fun sightseeing opportunities. Summer concerts – some free-can be enjoyed at the Jay Pritzker Pavilion, and on hot summer days, the Crown Fountain is a fun place to play and cool off.
The pier was built in 1916 and was named in honor of the naval veterans from WWI. The naval connection continued when the pier was used by the US Navy as a training center during WWII. Today, the revitalized Navy Pier is a multiuse popular Chicago destination with lots of restaurant options and activities for the whole family.
The Chicago Children’s Museum will entertain the youngest family members, while the Chicago Shakespeare Theater will appeal to the older crowd, and the iconic Ferris wheel will be fun for all ages. During the summer, Navy Pier puts on a fireworks display a couple of times a week and during the Christmas season be sure to check out the Winter Wonderfest.
The Palmer House is another one of Chicago’s great historic hotels which is now part of the Hilton collection. It was the first hotel in the city to have elevators and the first hotel to provide light bulbs and telephones in its guest rooms.
I like to go there for a happy hour drink in the lobby bar under the highly decorative frescoed ceiling or take in afternoon tea at the Lockwood Restaurant. Be sure to try one of their brownies which were invented in the Palmer House kitchens specifically for the 1893 Columbian Exposition World’s Fair.
The Shedd Aquarium is the third museum in Chicago’s Museum Campus and is my favorite of the three. It was built in 1930 and for a long time this 5 million gallon aquarium was the largest in the world.
I never tire of walking through the classic galleries looking at the realistic underwater habitats from the Caribbean or the Amazon. It’s a popular attraction with locals as well as with tourists, so it can get quite busy. I suggest getting there when it first opens to avoid the crowds.
Signature Room at the top of the John Hancock Building
For a short time after it was built in 1968, the 100 story John Hancock Center was the second tallest building in the world and the tallest skyscraper in Chicago. While it has long lost those titles, it still remains my favorite tall building in the city’s skyline. The observation deck has 360 degree views across Lake Michigan and the city. You can pay to take the high speed elevator to the 94th floor 360 Observation Deck, but for the same views, I prefer to spend my money at the 96th floor Signature Lounge.
Each time I am in the city, I try to end one day by watching the sunset from the Signature Lounge while I enjoy a drink and a snack. It gets very busy at that time of day, so try to get there at least 45 minutes to an hour before sunset to get a good seat. Ladies, for some of the best views, head to the ladies room which has floor to ceiling windows looking out across the southern lakeshore. It’s a popular selfie spot.
Chicago has invested in accessible public street art since the first big sculpture was installed by Picasso in 1967. Since then, many other sculptures by famous modern artists have been installed in the downtown area. The south Loop around Columbia College is also a showcase for many fine murals. You can discover all the great street art in my post The Best Chicago Street Art – Finding Murals, Sculptures and Other Public Art in the Windy City
Willis (Sears) Tower
I will always think of it as the Sears Tower even though it was renamed to the Willis tower in 2009. When the 110 story building was completed in 1973 it became the tallest building in the world, a record held for almost 25 years. The Skydeck on the 103rd floor offers an interesting observation experience: The Ledge. This is an all glass box that juts out from the side of the building and gives you unobstructed views of the street below your feet. This is a very popular attraction so I suggest going early in the morning before it gets too busy.
A little Further Afield
Chicago History Museum
Located at the southern end of Lincoln Park, the Chicago History Museum has been preserving and interpreting Chicago history since 1856. This is a fun museum to visit and learn about Chicago’s past. The collection is huge (about 22 million items) and you will find both permanent exhibits as well as rotating exhibits with varying themes.
Frank Lloyd Wright Studio tour
Frank Lloyd Wright is considered the father of the Prairie school of architecture and is one of the best known American architects. Take a short drive to the suburb of Oak Park to see a large concentration of houses designed by Frank Lloyd Wright. Here you will also find his home and studio.
Start with a Frank Lloyd Wright Home and Studio tour given by guides from the Frank Lloyd Wright trust, for an overview of the architect’s life and work. Then pick up a map for a self guided walk around Oak Park to see some of his many buildings, including the Unity Temple. Or if you have time, take another one of the Trust’s tours in this area.
You’ll want to spend at least half a day here, though you could easily spend a full day if you take more than one of the tours. To get here, you can take the green subway line west to the Oak Park station.
Garfield Park Conservatory
The Garfield Park Conservatory is one of the largest in the country. The eight different gardens under glass make a great escape during the cold and drab winter months. I was also attracted by the permanent installation by the glass artist Dale Chihuly. The first of Chihuly’s garden series was displayed here in 2001, titled “Chihuly in the Park: A Garden of Glass”. The Persian Lilly Pads which were displayed at this exhibition have been purchased by the Garfield Park Conservatory and are now on permanent display.
You can easily get to the conservatory using the green subway line to the Conservatory-Central Park Drive stop.
Lincoln Park Zoo
Since its founding in 1868, Lincoln Park Zoo has been free to visit. I’ve been visiting the zoo since I was a child and I never tire of seeing my favorite exhibits. I especially love seeing the polar bears, the penguins and the gorillas. The Farm-in-the-Zoo is also a fun experience for kids.
The zoo is in Lincoln Park, about 3 miles north of downtown. You can take a bus to get there but I find it easier to use one of the ride-share options.
Museum of Science and Industry
If you have the time, a trip to the Museum of Science and Industry is well worth it. The museum is not the easiest to get to using public transportation so I suggest getting there with a taxi or ride-share.
Among the unique interactive exhibits, you will find here are a full sized replica of a coal mine, a German submarine U boat captured in WWII and the command module of Apollo 8. I also never tire of seeing the miniature fully decorated and furnished fairy tale castle. My favorite time of year to visit is at Christmas time when the museum celebrates Christmas Around the World with 40 decorated trees that represent different cultures around the world.
North Avenue Beach and the Lakefront Trail
I spent my teenage summers hanging out at the lakeshore beaches. Chicago has many of them and each has its own personality and locals all have their favorites. Oak Street beach which is right on the northern edge of downtown is the “it” beach to see and be seen. But to experience a beach more like a local, rent a bike and pedal your way for about a mile north along the Lakefront Trail to North Avenue beach, located at the southern end of Lincoln Park. (You’ll fine one of the many bike rental kiosks across the street from the Drake Hotel).
An ocean liner inspired beach house is one of the fun features at North Avenue beach. You’ll find a couple of dining choices and food concessions here including an ice cream shop. There are also rental options for lounge chairs and umbrellas, bikes, wake boards and paddle boards. My favorite thing about this beach though are the fantastic views of Chicago’s downtown.
Second City Comedy Club
The Second City comedy theater has been a fixture in Chicago since 1959. Many well known comedians are alumni and quite a number have moved on to performing on the equally long running Saturday Night Live TV program (think Dan Aykroyd, Bill Murray, Mike Meyers and Tina Fey). An evening performance includes scripted material as well as a lot of improv based on audience suggestions, so you never know what you are going to get. As a result, each show is always different and always fun.
You can get to the Second City Theater on the blue or brown subway lines and get off at Sedgwick.
For baseball fans, catching a game at the historic Wrigley Field is a must. The stadium was built in 1914 and is listed as a National Historic Landmark. Unlike more modern baseball stadiums though, Wrigley Field sits in the middle of a residential neighborhood and has no big parking lots. The easiest way to get there is via the red subway line to the Addison station which lets you out one block from the stadium.
If you are not a baseball fan (or not a Cubs fan), or you just don’t have four or five hours to sit in a stadium, then a fun and informative behind the scenes stadium tour is a good option.
When is the best time to visit Chicago
Pretty much any time of year is a good time to go because there is always something interesting to do and see. Winters in Chicago get a bad rap, but if you want to tour Chicago on a budget, that is actually the best time to go and save some money.
Hope this guide helps you with your visit to my favorite city.
Thanks for visiting.