A Weekend in Chicago: How to Make the Most of 2 Days

January 20, 2020

Chicago showcases numerous attractions and activities for visitors of all ages.

From acclaimed museums and revered architecture to top-rated restaurants, you're bound to have a good time. If you only have a weekend in Chicago, you can still hit the top spots in the city before heading back home. Read below to learn how to make the most of 2 days in the Windy City.

Experience thrills on the Centennial Wheel or the Pepsi Wave Swinger in Chicago, Illinois, USA

Experience thrills on the Centennial Wheel or the Pepsi Wave Swinger!

Day 1: Magnificent Mile, Millennium Park, 360 Chicago, & Navy Pier

When you have one weekend in Chicago, you'll want to see the top locations without feeling overwhelmed. Consider spending the first day leisurely taking in the city skyline, shopping, and spending the evening on the Pier.

Magnificent Mile

The Magnificent Mile boasts incredible shopping, dining, accommodations, and entertainment choices that fit any budget. Whether you’re searching for affordable fashion or designer boutiques, you can find it all strolling down North Michigan Avenue. This scenic district enables visitors to see attractions such as the Chicago Sports Museum, the Historic Water Tower, art galleries, theaters, bars, gourmet food, and beyond! At the end of the day, stroll along the Chicago River and grab a bite at any of the dozens of eateries nearby. Also, you can find more than 70 hotels on or near the district.

view of chicago skyline at sunsetMillennium Park

This gorgeous urban park features the Cloud Gate sculpture (“the Bean”), so if you want that iconic Chicago picture, you know where to go. Other sightseeing spots include Pritzker Pavilion, the beautiful Lurie Garden, and glorious works of art like the Crown Fountain. Moreover, the park hosts numerous events throughout the year, so be on the lookout for concerts, free events like yoga practice, and food festivals.


360 CHICAGO enables guests to gaze at the city from 1,000 feet up in the air. Located on the 94th floor of the John Hancock Center, visitors can see stunning perspectives of Chicago and Lake Michigan. Take the 40-second ride in one of the country’s fastest elevators to the observation deck for the best views! Open daily from 9 am to 11 pm, experience one of the city’s best attractions when spending 3 days in Chicago. You can also see four neighboring states in the distance, as well as ride TILT, a one-of-a-kind tilting ride with awe-inspiring views.

Father and child viewing the city at 360 Chicago during sunset - Chicago, Illinois, USA

photo credit: 360 CHICAGO via Facebook

Navy Pier

Don’t skip out on the Navy Pier! With so many attractions such as the Chicago Shakespeare Theater, the iconic Centennial Wheel, theme park rides, and the Chicago Children’s Museum, guests of all ages will love this entertainment center. You can also capture views of the river as well, the city skyline, play a round of mini-golf, catch a movie in the Navy Pier IMAX at the AMC, and much more. Look out for concerts, free events, and seasonal events as well!

Day 2: SkyDeck, Field Museum, & Evening Segway Tour

Spend Day 2 in Chicago at the SkyDeck and Field Museum. Afterward, end the day with an informative Segway tour.

SkyDeck Chicago

Situated on the 103rd floor of the Willis Tower, visitors can experience unparalleled views at 1,353 feet up in the air! See Chicago from a unique perspective up in the SkyDeck, open 365 days a year. This thrilling attraction presents top-rated exhibits, theater presentations, and more! Moreover, guests can step out on The Ledge’s glass boxes, which extend approximately 4.3 feet from the deck. Overall, guests can see four states, 50 miles, and 360-degree views.

View looking down from the Skydeck in Chicago, Illinois, USA

photo credit: Skydeck Chicago via Facebook

The Field Museum

Head to the Field Museum to view a wide breadth and selection of objects and artifacts, as well as fascinating exhibitions. Connect with scientific discoveries and pieces of natural history with exhibits such as SUE, the most complete T-Rex skeleton, the famous Tsavo Lions, gorgeous gemstones and minerals, Ancient Egyptian artifacts, and much more! Note that the museum is open every day except for Christmas Day from 9 am to 5 pm. With over 100 years of curating experience, you don’t want to miss out on the Field Museum when you have 3 days in Chicago.

Chicago Evening Segway Tour

See Chicago from a unique, thrilling perspective. The Chicago Evening Segway Tour takes riders to iconic locations like Grant Park, Lake Michigan Lakefront, Buckingham Fountain, and the Museum Campus with an expert guide narrating along the way. This two-hour small group tour through the Windy City will take your breath away as you behold the sunset over the city skyline.

A Weekend in Chicago: The Best Places to Eat

From Puerto Rican cuisine and deep dish pizza to fusion Filipino-Cuban fare, Chicago hosts plenty of restaurants to satiate any craving. When you only have one weekend in Chicago, check out any of these top-rated restaurants:

Spend a Weekend in Chicago

However you plan to spend your 2 days in Chicago, you'll enjoy the city sights and Midwestern charm. To save further and gain more ideas, head to Tripster Chicago.

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Written By Talena


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