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Chicago, Illinois is one of the most iconic cities in the US. After visiting all 50 states, I can confidently say that it deserves a spot on your travel bucket list! Nicknamed the “Windy City” for the year-round breeze that blows off nearby Lake Michigan, the city can experience a wide fluctuation in temperature. You’ll want to plan your activities accordingly depending on the time of year, and this Chicago 3 day itinerary is here to help you! Without further ago, here’s how to spend 3 days in Chicago.
Where is Chicago located?
Chicago is located in the midwest US state of Illinois, on the southwestern edge of Lake Michigan. It’s about 2 hours away by car or train from Milwaukee, Wisconsin and only 40 minutes away from Indiana and the beaches of Indiana Dunes National Park.
When is the best time to spend 3 days in Chicago?
Chicago’s temperatures fluctuate dramatically with the seasons, thanks to its geographical location in the US and cool breeze that blows off Lake Michigan.
As I often recommend with any other destination, the shoulder seasons are the best times of year to visit Chicago! The temperatures are mild from April – June and September – November (averages are in the 60°s F).
The summer months of June – August see the hottest months, with temperatures reaching put to 85° F. “Chi Summer” is well-known for being a total vibe, with baseball games, boat days on the lake, music festivals, and rooftop bars. However, expect to pay A LOT for accommodation and flights this time of year.
Winter is the quietest time of year to visit Chicago but will be freezing. If the 20-30° F temperatures weren’t already a turn off, picture a cold lake breeze nipping at you on top of it! Honestly, we visited in early May and even this time of year had a little chill in the air. I couldn’t imagine living here in the winter months… and I’m from Boston.
How to get to Chicago, Illinois?
As mentioned above, Chicago borders the nearby states of Indiana and Wisconsin and is quite accessible by car from both.
Additionally, the city is home to two international airports offering thousands of daily flights to 200+ destinations. Chicago O’Hare international Airport is of the largest airports in the world and has 4 terminals. It’s just 16 miles from downtown Chicago. Chicago Midway is only 11 miles from downtown Chicago and offers more value-oriented, domestic flights.
Chicago’s iconic Union Station serves both Amtrak and Metra lines. It’s located centrally in the city and has restaurants, retail shops, and event spaces within. Amtrak has routes covering most of the US and Canada, and offers high-speed trains to more than 500 destinations daily. Additionally, Metra Rail is the local commuter rail in the area that connects the outlying suburbs to downtown Chicago.
I took the Amtrak from Union Station to Milwaukee, Wisconsin and really enjoyed the 2 hour ride!
The South Shore Line also runs through the city and connects Chicago with northern Indiana and the South Bend Airport. I rode this line for 40 minutes into the city from Indiana Dunes National Park, which is an easy day trip from the city! If you have more than 3 days in Chicago, consider spending a day here.
How to get around during your 3 days in Chicago?
Downtown Chicago is quite walkable as its streets are organized in a grid system. There is also Uber + Lyft widely available if you choose not to rent a car. Another common method of transportation within the city is the CTA, or the Chicago Transit Authority. This is the nation’s second largest public transportation system (the first is the NYC subway!). It operates Chicago’s 8 “L” train lines and over 100 bus routes.
We didn’t use the public bus during our weekend in Chicago, but I do recommend using the L. The L is unique as it runs mostly above ground! Although there are some traditional below ground subway lines too. The Blue Line, which connects O’Hare with downtown, and the Red Line, which connects the North to the South, both run 24/7.
Pro-tip: If you’re looking for something a bit more adventurous, you could also ride the Chicago Water Taxi system! Although these only operate seasonally during the summer months.
Recommendations for Accommodation
First time visitors to Chicago will want to stay in The Loop / downtown area for optimal walkability to nearby attractions. Additionally, the Magnificent Mile (covered below) is known for its luxury accommodations and shopping, and may be a better fit for more seasoned visitors.
We stayed at the Blackstone Hotel ($$) I highly recommend for the sleek guest rooms and central location on S. Michigan Ave!
Chicago 3 Day Itinerary
Day 1 of the Weekend in Chicago Itinerary
Self guided walking tour of the The Loop
Assuming this isn’t a full day of exploring due to AM travel and getting settled at the hotel, just spend a few hours this afternoon familiarizing yourself with downtown Chicago! Maybe this means riding the L, walking through Grant Park, or exploring the banks of Lake Michigan. If it’s warm enough, maybe even go for a quick swim!
Dinner at Lou Malnati’s Pizzeria
This is a MUST visit during 3 days in Chicago! Lou Malnati’s is a popular deep dish pizza chain located within the city. There are a few others, but every blog I read and local I talked to recommended this one, so now I am sharing it with you! This chain started in the 1940s in the city and has had a family-owned, secret recipe ever since. There are numerous locations throughout the city, but we went to the one in the Printer’s Row neighborhood near Eighth Street.
Address: 805 S State Street, Chicago, IL 60605
Bonus: Check out Chicago’s speakeasies, club scene, see a comedy show, or enjoy a historic crime tour after dinner!
Day 2 of the Weekend in Chicago Itinerary
Grab breakfast at Goddess and the Baker
This cafe is famous for its yummy food, treats, and of course — coffee bar! The Goddess and the Baker has both indoor and outdoor seating (during the warmer months) and is the perfect way to fuel your day of following this 3 days in Chicago itinerary.
Plus, they have a location right near Millennium Park, so I highly recommend starting the morning here. We brought our coffees to go to enjoy in the park.
Address: 33 S Wabash Ave, Chicago, IL 60603
Explore Millennium Park
After grabbing a quick breakfast and/or coffee this morning, head to Millennium Park bright and early this morning to beat the crowds! Millennium Park is a public park located within Chicago’s Loop that is world-famous for Cloud Gate. This sculpture was unveiled in 2005 and has been an icon of the city ever since. It’s best known as “the Bean” and is the ultimate Chicago photo opp.
There’s an event space in this park called the Jay Pritzker Pavilion & The Great Lawn, along with the equally as impressive Crown Fountain. Lurie Garden is a botanic garden located here as well. The pavilion offers numerous free events throughout the year, such as the Chicago Jazz Festival. Don’t miss it during your 3 days in Chicago!
Address: 201 E Randolph St, Chicago, IL 60602
See the Chicago Theater
Located just a few blocks from Millennium Park, the Chicago Theater is another must-see during a weekend in Chicago! This theater offers Broadway in Chicago performances and is a fantastic hub for entertainment in the city. Unfortunately when my family visited, it was still closed due to the pandemic so we just took photos from the outside!
The Chicago Theatre, originally known as the Balaban and Katz Chicago Theatre, is a landmark theater located on North State Street in the Loop area of Chicago, Illinois. Built in 1921, the Chicago Theatre was the flagship for the Balaban and Katz group of theaters run by A. J.
Address: 175 N State St, Chicago, IL 60601
Walk along the Chicago Riverwalk
The Chicago Riverwalk is a scenic walkway that runs alongside the Chicago River. This 1.25-mile long path is free to the public and is open from sunrise to about 11 pm. There are 4 distinct districts along the Riverwalk: The Confluence, The Arcade, The Civic, and The Esplanade.
During the warmer months, there are numerous restaurants and bars with outdoor dining right along the river here!
Experience the SkyDeck at the Willis Tower
Formerly known as the Sears Tower, Willis Tower has been an iconic part of the Chicago skyline since 1973. At 110 stories high, Willis Tower is also one of the largest skyscrapers in the world. It’s an office building, event space, tourist attraction, and so much more.
The Skydeck is open year-round, seven days a week. The viewing tower is popular with locals and visitors alike, so be sure to grab tickets in advance! The SkyDeck experience walks visitors through the history of the building, construction, and other interactive exhibits before bringing guests up a high-speed elevator to one of the top floors in the Willis. It takes about 30 minutes to enjoy the exhibits and another 30 minutes or so to enjoy the views at the top.
As you explore the SkyDeck, be sure to visit The Ledge: a glass balcony extending four feet outside Willis Tower’s 103rd floor. At 1,353 feet in the air, it’s quite thrilling looking down! On a clear day, you can see into Wisconsin and Indiana. Be sure to snap a photo here!
Pro-tip: Hungry? Visit the Catalog at Willis Tower. Catalog is an evolving, five-level space, featuring new dining, specialty retail, and entertainment options. This could be a great place to grab lunch if you’re following this Chicago 3 day itinerary.
Address: 233 S Wacker Dr, Chicago, IL 60606
Architecture River Cruise + Navy Pier
My last recommendation for this very full day in Chicago is to enjoy an architecture river tour with Shoreline Sightseeing! Shoreline Sightseeing has award-winning tours that showcase the city’s rich architectural heritage. Chicago has one of the most unique skylines I’ve ever seen, so definitely learn about the history behind the 40+ famous buildings! Plus, the river tour allows you to get close-up views and the best photo-ops in the city.
Shoreline has been Chicago’s leading river touring company for 80 years. It’s a popular activity on a Chicago 3 day itinerary, so definitely grab tickets in advance for this as well.
The architecture tour is 75 minutes long, serves beverages on board, and departs from two locations in the city:
- The southwest corner of Polk Bros Park at Navy Pier
- The northeast corner of the Michigan Avenue Bridge at the Apple store
Since this is an evening tour, it will be the perfect time to grab dinner on the Navy Pier! There are numerous restaurants in this area to choose from, along with an iconic ferris wheel to enjoy. That’s a wrap for day two!
Day 3 of the Weekend in Chicago Itinerary
Visit the Starbucks Reserve + shop in Magnificent Mile
Begin your final morning in Chicago at the Starbucks Reserve for coffee and breakfast! The Chicago Roastery opened in November 2019 along the Magnificent Mile in Chicago. You can think of a Starbucks Reserve as a speciality coffee shop, with an expansive food menu, unique drink offerings, merchandise, and coffee roasting on site. Make sure to stop here during one of your 3 days in Chicago!
Fun fact: There are numerous Reserves around the world, including Seattle, Milan, Tokyo, New York, and Shanghai! I’ve been to quite a few and have included stops here in to my recommendations on various itineraries, such as a Pacific Northwest road trip.
Address: 646 Michigan Ave, Chicago, IL 60611
Once you’re caffeinated, explore the rest of Magnificent Mile: a premier shopping destination within downtown Chicago. This neighborhood covers 13 blocks of Michigan Ave and is famous for its luxury stores, posh hotels, swanky dining options, and more! If you aren’t full from the Reserve’s delectable menu, there are plenty of options for lunch in this area!
Visit the Art Institute of Chicago
My last recommendation to wrap up this itinerary for 3 days in Chicago is to wander around the Art Institute of Chicago. Located within Grant Park in the Loop on the shores of Lake Michigan, the Art Institute is a must — especially for rainy, cold days. The Art Institute of Chicago is one of the oldest and largest art museums in the world. It was founded in 1879 and is open every day of the week aside from Tuesdays and Wednesdays. Admission for adults is $32, and tickets can be purchased online or in-person.
I would set aside 2-3 hours to explore this museum on your own, and an extra hour if you opt for a free walking tour.
Pro-tip: The Art Institute of Chicago provides free access to children under 14, Chicago teens under 18, Link and WIC cardholders, and Illinois educators every day, as well as to Illinois residents on certain days throughout the year.
Address: 111 S Michigan Ave, Chicago, IL 60603
From here, I hoped on am Amtrak train and headed up to Milwaukee, Wisconsin to continue my travels throughout the midwest. So, that wraps this itinerary for 3 days in Chicago! Whether you’re spending a weekend exploring the city, or driving through on a USA road trip, I hope this blog post provided you with all the info you needed. See you next time!
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