Chicago is my favorite big city in America to visit. The culture of the city is different than any other in America because it is where traditional Midwest values meet seedy mob history. The city itself is similar to New York City in that the skyscrapers were built during a time when architecture and lavish décor were more important than cost cutting. And public transportation or walking is how people get around. Whether you are a first-timer or a frequent-visitor, this 3 day Chicago itinerary will let you see the best of the Windy City’s culture, architecture, and attractions.
Best Times of Year to Visit
The most popular time to visit Chicago is the summer months of June through August when the weather is warm and kids are out of school. However, the best months to visit for optimal weather and fewer crowds is April to May and September to October. Winter time is the least busy time (and significantly cheaper time) to visit if you can stomach the possible extremely frigid weather and lake effect snow. Most of the times I have visited Chicago has been in the winter. If this Southern girl can handle it, so can you!
How to Get Around Chicago
Chicago has two major airports: O’Hare and Midway. Both airports are relatively close to downtown, ranging from 10 to 20 miles away. However drive times can vary from 20 minutes to an hour depending on traffic. You can take a taxi or ride share into the city and straight to you hotel for approximately $40.
However, you may opt to take the train if you are on a budget with ticket prices being $5 or less. The trains from both O’Hare and Midway leave every 8-12 minutes and take around 50 minutes. You will need to weigh cost vs. time to see which transportation works best for you. From O’Hare you will take the Blue Line, and from Midway you will take the Midway Orange Line to Union Station.
Once you are in the city, you can mostly walk to get around the downtown area. I usually end up walking 6-7 miles per day when I am in town. The El Train (Elevated Train) and Subways of the Chicago Transit Authority (CTA) are the cost-efficient way of getting around if your destination is not walkable. Click here for a rail system map.
Eating Around Chicago
Chicago is a foodie’s paradise. There are so many local, high-quality restaurants to choose from. I do recommend making reservations at least a week in advance at any restaurant you are dying to eat at. When I visited in February, the least busy time in Chicago, I struggled to find availabilities at my top restaurants.
Even with the high class eateries, the two most famous cuisines of Chicago is the deep dish pizza and Chicago style hot dogs. I am not a hot dog fan, so I do not have any recommendations for you on where to get the best Chicago style hot dog. But I am a pizza connoisseur. I recommend deep dish pizza at Pizzeria Uno, Giordano’s, or Gino’s East. The pizzas take around 45 minutes to cook, so if you arrive famished, you will need to order an appetizer.
Make sure to stop at Garrett’s popcorn at the beginning of your trip, so you can snack on it during the coming days. Be prepared to wait in lines down the street for this iconic popcorn. My favorite flavors are Buttery (of course!) and Pecan CaramelCrisp. However, the most popular purchase is the Garrett Mix, which is a combination of cheddar and caramel popcorn.
Fun Facts About Chicago
- Chicago is the third largest by population in the United States.
- The Great Chicago Fire of 1871 claimed about 300 lives, destroyed some 17,450 buildings covering almost 3.5 square miles.
- Chicago is considered the home of the world’s first skyscraper. The Home Insurance Building was built in 1885 and was originally 10 stories tall.
- “Windy City” originated based on the area’s windstorms and because the politicians were known for being full of hot air.
- Already making history as one of the first black physicians in the city, Northwestern University graduate Daniel Hale Williams performed the nation’s first-ever open-heart surgery.
- In the largest public earth-moving project ever completed, in 1900 the Chicago River was engineered to flow backwards! This incredible achievement has a very practical purpose: to divert sewage away from Lake Michigan’s freshwater supply.
- The first atom was split in 1942 at exactly 3:25 p.m. on the University of Chicago grounds. The moment is regarded as the start of the atomic age. Henry Moore’s Nuclear Energy sculpture marks the spot today.
DAY 1 – Sights and Shopping
I recommend arriving the night before, so you can start fresh in the morning for the first of your 3 day Chicago itinerary. Enjoy breakfast or brunch before heading out. We ate the hotel complimentary breakfast every morning to save money.
Millennium Park
Start your 3 day Chicago itinerary at the famous Cloud Gate (a.k.a. The Bean) in Millennium Park. Since its installation in 2004, the Bean has become the main landmark of Chicago, and hoards of people flock here for pictures. You should definitely come here first thing in the morning to avoid some of the crowds. The art sculpture was designed with liquid mercury in mind. Its smooth, reflective shell offers the perfect spot for reflection pictures of the city, sky, and the people that visit it.
Millennium Monument at Wrigley Square is an almost exact replica of a peristyle that sat in the same spot in the early 1900s. If you walk up close, you will see names of the 122 founders of the park engraved into the monument.
Check out the modern architecture of the Jay Pritzker Pavilion. This outdoor amphitheater can accommodate 11,000 patrons and is an interesting spot to see a live show.
Grant Park
Just south of Millennium Park lies Grant Park. The most iconic landmark here is the Buckingham Fountain, which is operational typically from May to October. This fountain is one of the largest in the world, and it performs a water display for 20 minutes every hour, at the top of the hour. The center jet can reach heights of 150 feet.
Make sure to take time to admire Lake Michigan which is so large it looks like the ocean.
Chicago Cultural Center
The Chicago Cultural Center was once Chicago’s first central public library but is now home to many free art exhibits, dance and music events, films, and lectures. Because of its beautiful architectural designs inside, this is my favorite building in Chicago. The floors, walls, and staircases are made from the most extravagant materials such as rare imported marbles, polished brass, fine hardwoods, and mosaics of Favrile glass, mother-of-pearl and colored stone.
The best part of this building, though, is the two stained glass domes. The dome on the south side of the building is the world’s largest Tiffany dome at 38-foot diameter and 30,000 pieces of glass. The Chicago Cultural Center is a unique building and is a must do on your 3 day Chicago itinerary.
Magnificent Mile
Continue north on Michigan Avenue, and be prepared to shop ’til you drop! This stretch of Michigan Avenue is known as Magnificent Mile. There are still architecturally and historically significant buildings along this route, such as the Wrigley Building, Tribune Tower, and the Old Chicago Water Tower. But a majority of your time here will be spent perusing upscale and specialty stores.
If you are a coffee-lover (and even if you’re not), make sure to visit the Starbucks Reserve Roastery. This 5-story Starbucks is an experience in itself. The difference floors offer different services including an experimental coffee area and a fully stocked bar where they specialize in espresso martinis. There are currently only 6 of these Starbucks Reserves in operation worldwide.
John Hancock Building
Towards the end of the Magnificent Mile, you will find the 100-story, 1,128-foot tall John Hancock Building. The building was designed using exterior X-bracing as part of its tubular system, which is a technique used to achieve extreme heights. The X-bracing also allows for an open inside floorplan.
For the best views of the Chicago skyline, get tickets to 360 Chicago Observation Deck where you can access the 94th floor of the John Hancock Building. There is an option to get Tilt tickets where you hold on to the window panes as they tilt 30 degrees towards the street below. Also, there is a 360 Chicago Bar located on this floor. Get your tickets to this thrilling experience ahead of time to ensure availability of ideal times. I recommend going an hour or so before sunset to see the city during the day and shortly after the sunsets.
If you want the views without the Tilt or ticket prices, you can go to The Signature Room and Lounge on the 95th and 96th floors. If there is time during your 3 day Chicago itinerary, you could also check out the SkyDeck at the Willis Tower where you can walk out on a glass-bottom walkway over the street below.
DAY 2 – Museum Day
Chicago has some really great museums that you can spend several days exploring. But for this 3 day Chicago itinerary, you should spend just one day at museums. Pick one or two to visit depending on long you think you will spend at each museum. I tend to see museums at a very quick pace, so I know I could easily visit 2 museums in one day. The Art Institute of Chicago and the Field Museum are the two I would recommend. The Field Museum opens at 9am where the Art Institute opens at 11am, so you should visit the Field Museum first to make the most of your day.
Field Museum
The Field Museum hosts natural history artifacts and exhibits that span 4.6 billion years into the past. This museum has several dinosaur skeletons including Maximo the Titanosaur, the largest dinosaur to ever exist, and Sue, the most complete Tyrannosaurus Rex ever discovered. In addition to the prehistoric creatures, the Field Museum exhibits many artifacts from ancient civilizations.
Art Institute of Chicago
The Art Institute of Chicago is home to some of the world’s most recognizable art pieces, and you could spend hours analyzing and admiring the many masterpieces inside the museum. However, if you want to see the best of the museum in about an hour, here are the pieces I recommend in order of viewing.
1.Paris Street; Rainy Day by Gustave Caillebotte, 1877 – Gallery 201
2. Woman at Her Toilette by Berthe Morisot, 1895 – Gallery 201
3. A Sunday on La Grande Jatte by Georges Seurat, 1884 – Gallery 240
4. Self-Portrait by Vincent Van Gogh, 1887 – Gallery 241
5. Water Lilies by Claude Monet, 1906 – Gallery 243
6. Nighthawks by Edward Hopper, 1942 – Gallery 262. Getting to the 260s galleries is a little tricky. When you get to the Sky Above Clouds IV painting, turn right which will lead you to an elevator. Hit the handicap button inside the elevator. After you exit the elevator, turn right and walk up the stairs. The galleries will be on the right.
7. American Gothic by Grant Wood, 1930 – Gallery 263
8. The Old Guitarist by Pablo Picasso, 1904 – Gallery 391. To get to the 300s, you will need to get back on the elevator from earlier and go to the 2nd floor. Turn right and continue walking to the complete opposite side of the building. You will see stairs that lead you to the third floor.
Other museum options include Chicago History Museum, Museum of Science and Industry, Adler Planetarium, and Shedd Aquarium.
DAY 3 – Tours and Events
The last of your 3 day Chicago itinerary should be spent doing tours and/or attending events. Start the day with a tour. My favorites are the 90-minute Chicago River Architecture Tour and the Chicago Crime and Mob Bus Tour (2 hours). If no special events are happening in Chicago during your visit, you can do multiple tours. Another neat excursion to try is the Chicago Food Tour. If you are a baseball fan, take the El train to Lincoln Park and do a tour of Wrigley Field, home of the Chicago Cubs.
If your timing works out, I suggest attending a game, event, or festival. Here are some options that you can choose from:
Major Sporting Events
- Chicago Bulls (basketball) – October to April
- Chicago Bears (football) – September to January
- Chicago Cubs or White Sox (baseball) – April to September
- Chicago Blackhawks (hockey) – October to April
Events and Festivals
- Restaurant Week – January and February
- St. Patrick’s Day Downtown Parade and River Dying – March
- Chicago Pride Parade – June
- Chicago Blues Festival – June
- Taste of Chicago – July
- Chicago Air and Water Show – August
- Lollapalooza – August
- Chicago Jazz Festival – September
- Chicago Marathon – October
- Christlkindmarket Chicago – November and December
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