Three Days in Chicago: The Perfect Weekend Chicago Itinerary

Chicago, the Windy City, is such a fun and interesting city to visit in the United States. Although not as popular as Los Angeles and New York, Chicago has a ton of fun things to do and will have you visiting again and again. Three days in Chicago is the perfect amount of time for a first trip and makes for a fabulous long weekend. Chicago’s central location makes for an easy flight from anywhere in the United States. 

Want a guided tour to start out your trip and get acclimated to the city? Then check out Guru Walks for a free guided tour. You can book online to reserve your spot and pay what you wish when you get there. Check out the tours in Chicago here.

US Ghost Adventures is an awesome company that offers a variety of guided tours and haunted experiences across different cities in the United States. Visitors can learn the compelling history and stories of the paranormal and the city’s darker side. Make sure to check out the variety of tours offered in Chicago here. They are very affordable too!

Disclaimer: Special thanks to the Chicago Tourism board for hosting me at several excursions and restaurants on my trip to Chicago! As always, all thoughts and opinions remain my own. This post contains affiliate links. I may earn a commission at no cost to you!

History of Chicago

The area of Chicago was originally inhabited by the Potawatomi Native Americans until the mid-1700s. Later, Jean Baptiste Point du Sable established a settlement in the area in the 1780s, thus becoming known as the “Founder of Chicago.” After some clashes with the Native Americans, the Chicago area was turned over to the US military, but conflict with the Native Americans continued. 

In 1833, the town of Chicago was officially established and then became a city in 1837. The city quickly became a transportation hub between the east and the west with main trains passing through. This brought more immigrants and wealth to the area establishing it as a thriving metropolis and political center. 

Throughout the 1900s, Chicago aided the war effort and continued to grow. The Great Depression hit Chicago hard, but it later bounced back and began to grow into the city it is today. 

When to Spend Three Days in Chicago

Chicago is a different experience depending on what season you visit. I am one of the crazy people who love Chicago in the wintertime because the city is not crowded and there are a ton of unique things to do in the wintertime. However, prepare for it to be very cold and windy. If cold is not your thing, visit Chicago in the fall or late spring. Summer can get very hot and humid but Chicago has a ton of fun things to do during that time. 

How to Get to Chicago

Chicago has two major airports: Chicago O’Hare and Chicago Midway. O’Hare is very large and tends to have more flights. However, Midway is a little bit closer to the downtown area and much less busy than O’Hare. 

From O’Hare, it is about a 30-minute drive to Downtown Chicago or an hour by public transportation. You can take the blue line to the red line on the L to get downtown. 

From Midway, it is about a 25-minute drive to downtown or 45 minutes by public transportation. You can take the orange line to the red line on the L. 

Transportation in Chicago

The cheapest way to get around during three days in Chicago is by taking the “L” train. The “L” train got its name from being “elevated” off the ground, so it was shortened to “L” as its popularity grew. It costs $2.50/ride or you can buy a day pass for $10, 3 day pass for $20, or a 7 day for $28. Uber/Lyft is also convenient if you have a larger group. 

Where to Stay in Chicago

TripAdvisor is a great place to start your hotel search. Search for the best Chicago hotels here!

The best area to stay in Chicago is in River North or near the Magnificent Mile. This is most conveniently located to most places and is close to several L stops. Make sure to check out Priceline Express Deals to score some great deals. One time I got a Hampton Inn Downtown for $55/night and the Westin for $85/night. 

Check out these hotel options too!

• Thompson Chicago
• Hyatt Regency Chicago
• Hyatt Centric Chicago Magnificent Mile
• Intercontinental Chicago Magnificent Mile
• Holiday Inn Express Chicago -Magnificent Mile
• The Westin Michigan Avenue
• Aloft Chicago Mag Mile
• Hilton Chicago
• Hampton Inn Chicago Downtown

What to do During Three Days in Chicago

GoCity Pass

GoCity offers a ton of different sightseeing passes for cities around the world. These passes allow you to visit the best of each city for one low price, rather than paying individually for each attraction. I have used it in several cities around the world and would recommend getting a GoCity pass! Check out the options for the Chicago GoCity pass here.

Day 1

Brunch at Flora Fauna

Cost: $$

Hours: Mon-Thurs: 4-11pm, Fri: 4pm-12am, Sat: 10:30am-3pm, 4pm-12am, Sun: 10:30am-3pm, 4-11pm

Start your first of three days in Chicago with brunch at Flora Fauna. They offer a lot of fun and unique dishes, many of which are vegetarian and vegan friendly. You can get a bottle of champagne for the table and they will give you a variety of juices to make mimosas. You can also choose a base cocktail and then they have different flavors you can add to it. I recommend either option and make sure to get the sweet potato waffle fries. 

The Art Institute of Chicago

Cost: $25 General Admission

Hours: Open Daily from 10:30am to 5pm and until 8pm on Wednesday, Thursday, and Friday. 

When spending three days in Chicago, you must visit the Art Institute even if you are not a huge art person. This is one of the best art museums in the United States along with the MET in New York City. 

The museum was founded in 1879 and is one of the oldest art museums in the United States. It contains over 300,000 works of art including popular pieces such as Georges Seurat’s “A Sunday on La Grande Jatte” and Grant Wood’s “American Gothic.” My personal favorite is the “Picture of Dorian Gray.” You will want a couple hours to peruse the art collections.

Millenium Park

Cost: Free

Another classic stop during three days in Chicago is Millenium Park. This is the location of the infamous “Bean” sculpture also known as Cloud Gate. This sculpture was created by Sir Anish Kapoor in 2004. Make sure to check out your reflection. It is free to walk around this public park. In the wintertime, there is ice skating in the park, and in the summertime, it often hosts various events. The Art Institute and Chicago Cultural Center are also located within the park. 

Eat Chicago Style Pizza

Cost: $$

Hours: Varies by location

For dinner tonight, grab some Chicago-style pizza. There are a ton of various pizza joints, but three of the top favorites are Gino’s East, Giordano’s, and Lou Malnati’s. All are really delicious options for a tasty meal. 

Green Door Tavern/The Drifter

Cost: $

Hours: Tues: 5pm-12am, Wed-Fri: 5pm-2am, Sat: 5pm-3am, Closed Sunday and Monays

After dinner, head to Chicago’s best speakeasy, The Drifter. Although you may have to wait a bit, it is well worth a visit. Head towards the bathrooms, and look around to find The Drifter Speakeasy. If there is a show going on, there will be a $6 cover charge. 

When we visited, there was a burlesque show going on. Inside, their drink menu is on Tarot Cards and they have some unique drinks that change. They also have the option for a surprise drink where you can pull a fortune cookie out of a Buddha cookie jar. 

If you need a place to wait when getting into The Drifter, the Green Door Tavern is the upstairs pub. They serve plenty of appetizers and have a full bar. 

I/O Rooftop Lounge at the Godfrey 

Cost: $

Hours: Mon-Fri: 2pm-2am, Sat: 11am-3am, Sun: 11am-2am

The I/O Rooftop Lounge is a good alternative if you cannot get into The Drifter. This rooftop bar is a must when visiting Chicago as it offers nice views of Downtown Chicago. In the summertime, it is a great place to chill and relax in the sun. In the winter season, they have heated igloos. In order to visit these, you must make a reservation ahead of time. There is also a large indoor space with lots of standing room. 

Day 2

The Field Museum

Cost: $26 General Admission

Hours: Open Daily 9am-5pm

This morning, opt to spend some time at the Field Museum. Another one of my favorite museums in Chicago is the Field Museum. This is Chicago’s Natural History Museum and another very popular museum in the United States and one of the largest natural history museums in the world. 

It contains a ton of amazing exhibits from ancient cultures to scientific discoveries. You will not want to miss the dinosaur fossil area and the mummies. Make sure to check out the skeleton of Sue, the largest T-Rex species that has been discovered. 

Food Tour with Chicago Food Planet

Cost: $50 and up (but check Groupon for sales)

Hours: Varies by tour. Check the website for more information.

Another thing to do on your second of three days in Chicago is to head out on a Chicago Food Tour. I recommend doing the Iconic Food of Chicago tour if you have never been to Chicago before. This will give you a fantastic sampling of the foods Chicago is known for. If you have been to Chicago before, opt for the Gateway to the West Loop tour which takes you to some lesser-known food places in Chicago. 

Make sure to make a reservation in advance. Tours are offered at various times throughout the day. 

Skydeck at the Willis Tower

Cost: $26 General Admission, but make sure to check Travelzoo or Groupon for Discount Tickets

Hours: March-September 9am-10pm, October-February Sunday-Friday, 10am to 8pm and Saturday, 9:30am-9pm

This afternoon, visit the Skydeck at the Willis Tower. This is a unique experience when spending three days in Chciago. The 110-story skyscraper held the tallest building in the world for 25 years. It offers gorgeous views of the city and also the infamous “Ledge” experience. The “Ledge” experience enables visitors to step out into a glass box that extends 4.3 feet out from the Skydeck which leaves you standing 1,353 feet in the air. 

Drinks at The Signature Lounge

Cost: $5 and up

Hours: Sun-Thurs: 11am-12:30am, Fri-Sat: 11am-1:30am

An alternative to the Skydeck is to grab a drink at the Signature Lounge. This lounge offers the same views as the Skydeck from a floor below but for a much cheaper price. Non-alcoholic beverages start at $5 while alcoholic drinks start at $10. You can also grab some light bites to eat. Make sure to get there early as it does get busier in the evenings. 

Day 3

Chicago History Museum

Cost: $19 General Admission ($17 for Illinois Teachers)

Hours: Mon, Wed-Sat: 9:30am-4:30pm, Tues: 9:30am-9pm, Sun: 12pm-5pm

The Chicago History Museum is perfect for history lovers or people interested in learning about the history of Chicago. It focuses on the history of Chicago from its founding. It is a must for any history lover when spending three days in Chicago.

In 1856, the Chicago Historical Society founded the museum, but the original building burned down in the Great Chicago Fire of 1871. Many documents were lost during that time, but the museum was rebuilt and gained a ton of new manuscripts in 1920. Present-day, it contains tons of exhibits about the history of Chicago. 

Lincoln Park

Cost: Free

Hours: Varies by location

Lincoln Park is an area in the northern part of Chicago. It has various things inside of the park, the most notable of which is the Lincoln Park Zoo. It is a nice park to take a stroll through or stop for a picnic lunch. In the summertime, they host various concerts and other outdoor events. There is also a nice beach close by. Make sure to check ahead of time to see what events are happening at the park. 

Portillos

Cost: $

Hours: Varies by location

Portillos is a classic food stop to take during three days in Chicago. It is popular due to its Chicago hot dogs. I also enjoy their cheese fries. Outside of hot dogs, they also serve other American fare such as burgers, sandwiches, salads, pasta, and shakes. 

Chicago Architecture Center

Cost: $12 General Admission

Hours: 9:30am to 5pm

After lunch, head to the Chicago Architecture Center or the CAC. Here you can opt to visit the museum dedicated to the architecture of Chicago. It is known for its 3D printed model of Chicago. 

If you do not want to visit the museum, the CAC also offers about 85 walking, bus, boat, and “L” train tours. In the summertime, you can also take a cruise tour down the river, which is usually pretty popular. Partaking in one of these activities is a great contribution to spending three days in Chicago.

Goose Island Brewery Tour

Cost: $12 for a tour, $6 and up for pints

Hours: Wednesday/Thursday 12pm-8pm, Friday/Saturday 12pm-10pm, Sunday 12pm-6pm

To wrap up your last of three days in Chicago, head to the Goose Island Brewery for a tour. The brewery began in 1988 in the Lincoln Park area of Chicago. Tours last 45 minutes and take guests all over the facility. Throughout the tour, you will receive several samples of beers. At the end, you will receive a beer of your choice and a souvenir glass to take home. It was well worth the $12. 

More than Three Days in Chicago?

If you have more than three days in Chicago there are a ton of other awesome things to do in Chicago. You could easily spend an entire week visiting what the city has to offer. 

360 Chicago Observation Deck at the John Hancock Building

Cost: $22 General Admission, $5 for the TILT Experience, 25% off tickets during wintertime

Hours: 9am-11pm

An alternative to the Skydeck is the 360 Chicago Observation Deck. This also offers fabulous views of the city as well as the “TILT Experience” which tilts you out in a glass box over the city. This building was completed in 1969 and starts at 100 stories or 1,128 feet. They also host various activities each day of the week such as yoga, trivia, and happy hour. 

Auditorium Theater

Cost: $12 General Admission

Hours: Varies depending on the schedule of the shows. Check the website for more information.

The Auditorium Theater is the perfect Chicago stop for theater lovers. This building was the first major building to be built after the Chicago fire and was also worked on by Frank Lloyd Wright. In its early days, it even contained a hotel, office spaces, and a pharmacy along with the theater. 

Present-day, visitors can opt to take a tour, watch a show such as a Broadway Museum, or see various speakers speak. The building is also registered as a National Historic Landmark. A tour of the theater is a cool experience to learn about the history and unique facts of the theater. 

Chicago Pizza and Oven Grinder Company

Cost: $$

Hours: Mon-Thurs 4pm-7pm, Fri: 4pm-12am, Sat: 11:30am-12am, Sun: 11:30am-11pm

Over Grinder is another fantastic option for pizza. They are known for their pizza pot pies and Mediterranean Bread. You can choose the type of sauce (marinara or meat), and if you want mushrooms. If you order a salad or an appetizer, one half-pound pot pie is plenty for two people. 

Chicago Theater

Cost: Varies by event

Hours: Varies by event

The Chicago Theater was home to the first large and lavish movie theater in the United States. Today, it is home to many concerts, events, and shows. You can get tickets to the shows ahead of time or show up the day of to see what is available. At the very least, you will want to get a picture of the Chicago Theater sign. 

Garrett Popcorn

Cost: $

Hours: Varies by location

A trip to Chicago is not complete without a stop at Garrett Popcorn. They are popular due to their Chicago mix of popcorn: A mixture of Cheese and Caramel flavors. This is a great snack to munch on throughout the day or to take along on your flight home. 

Day Trip to Indiana Dunes National Park

Cost: $6 or Free in the offseason or with the America the Beautiful Pass

Hours: Varies by season and location

Less than an hour from Chicago lies Indiana Dunes National Park. This park contains various sand dunes and 15 miles of coastline along Lake Michigan. You can opt to get here by rental car (the easiest and most convenient way) or you can take the train. 

When at the park, you can choose to relax on the beach, choose one of the hiking trails to complete, or head to the visitor’s center to learn more about the wildlife in the park. Make sure to check out the Century of Progress homes, which were built for the 1933 World’s Fair. 

Walk along the Magnificent Mile

Cost: Free

Hours: Varies by store

The Magnificent Mile is Chicago’s most famous street with a ton of shops, hotels, and restaurants. It is the perfect place to start for any shopping lover. This mile-long street contains many of the world’s leading retail stores such as Macy’s, Nordstrom, Neiman Marcus as well as some smaller boutique stores. You could spend an entire day just walking around the area. 

Navy Pier

Cost: Free

Hours: Sun-Thurs: 11am-8pm Fri & Sat: 11am-10pm

Although Navy Pier is not my favorite spot to visit, it is a popular place to visit in Chicago. There is a ferris wheel, other rides, tons of restaurants, and it is the host to various special events throughout the year. During the Christmas season, it is all decorated for the holidays and really pretty to walk around. Be sure to check the website for more information about seasonal events. 

Pullman National Monument

Cost: Free

Hours: 9am-5pm

Another site run by the National Park system in Chicago is Pullman National Monument. This place is located about 30 minutes south of Downtown Chicago. Visitors can learn about the history of the area which was the first planned industrial community in the United States. The area also was infamous for the 1894 Pullman Strike which facilitated the creation of unions. 

When visiting you can walk around the area, visit the train exhibit in the visitor’s center, and take a tour of several of the buildings. Look at the website for more information as to tour times. It is free to visit the entire site. 

Sugar Factory

Cost: $$

Hours: Mon-Thurs: 11:30am-10:30pm, Fri-Sat: 10am-12am, Sun: 10am-11pm

The Sugar Factory is another fun place to grab a bite to eat or a unique drink. The food is your typical American fare, but the drinks are what you want to visit for. All of the drinks are very sweet and include candy in them. They also offer boozy milkshakes. They constantly come out with new surprise drinks and have specials. One of the drinks we got was like a pop-rock volcano that caused a mini-explosion. 

Grab a Drink at Three Dots and a Dash

Cost: $$

Hours: Sun-Fri: 4pm-2am, Sat: 2pm-3am

Three Dots and a Dash is a must-visit for any Tiki Bar lover. They offer a ton of cool and unique tropical drinks. The bar is hidden down an alleyway, so if headed into a dark alley, you are going in the right direction. It can get quite popular on the weekends, so make a reservation to ensure you get inside. 

Walking Tour by Free Tours by Foot

Cost: Free! Just make sure to tip your guide

Hours: Varies by tour. Check the website for more information. 

Another fun thing to do during three days in Chicago is a free walking tour! Free Tours by Foot offers a few different tours such as the Petway System tour. This tour takes visitors through indoor tunnels, paths, and ridges throughout Downtown Chicago. This is a great thing to do especially if you have not been to Chicago before. 

There are so many fun things to do during three days in Chicago. If you have more time, you could always visit Springfield and then St. Louis as part of this trip. 

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