What is There to Do During a Weekend Trip to Chicago?

March 22, 2015

Chicago is a key American city with a ton to keep you busy. This means that if you’re just going for a weekend trip, you have to be choosy about what you decide to do. Plan for three or four activities, see the sights, and eat some of the city’s iconic food. Here are a few suggestions.

Architecture River Cruise

If you’ll be in Chicago during the warmer months of the year, book the architecture river cruise. Interesting and educational, the cruise will give you all the history of the city’s iconic landmarks as well as its renowned skyline. In fact, your tour director will share this information with you almost building by building. During the tour, you’ll learn about structures by Skidmore Owings Merrill, Helmut Jahn and Mies van der Rohe. The tour also passes by the Old Post Office Building and the Willis Tower. If you haven’t spent a lot, or any, time in Chicago, this is a must-see experience. Along with learning about architecture in general, you’ll also get a first-hand feel of Chicago’s history.

360 Chicago

The iconic John Hancock Tower, which is on Michigan Avenue, recently renovated its observation deck. Stop by for an amazing photo of the city. Here, you can also learn more about Chicago’s legendary architecture. The observation tower is on the 94th floor, and along with viewing the city’s buildings, you’ll also have a view of Lake Michigan. A major benefit of going to the tower is that it is in a part of Chicago that you’ll want to explore. Plan to spend at least an hour here.

Rent a Bike

To see more of the city, rent a bike and take a ride along the waterfront. Full of parks, pathways and trails, you’ll get to see plenty by bike. With 26 miles of lakefront trails, you’ll enjoy your time getting in touch with nature. A bike excursion will also give you an awesome workout. Bike rentals are four hours long, but if you want to see more of the city, plan for a two-hour tour.

Wander Around the Art Institute of Chicago

Check out the city’s art side by visiting the Art Institute of Chicago. Recently rated by Trip Advisor as one of the best museums in the country, at the Art Institute, you’ll have the chance to see incredible works. In addition to contemporary art, decorative art and impressionist art, you’ll have the chance to see stunning photography, architecture and other types of design.

Picking Accommodations

Hotels near downtown Chicago with free parking offer value. Staying in the downtown area offers convenience since you can walk to many of the city’s interesting sites. Recommendations include the Hyatt Regency Chicago. It is an amazing place to stay in the city, and it’s close to the Navy Pier. The Hyatt is also within walking distance of Millennium Park and the Magnificent Mile, adding to the convenience during your stay.

Get Dinner

This iconic city features iconic food. Get a deep-dish pizza for dinner and a hot dog for lunch. While in Chicago, you should also try the popcorn and grab a brownie or one of the city’s gooey cinnamon rolls.

Taking a Quick Trip

Life is busy, so if you only have time for a short trip to Chicago, know that there’s still a lot that you can do. See the architecture, appreciate the art and take lots of pretty pictures. Chicago is one of those places that you’ll want to visit more than once.



Darpan Dodiya
Raleigh, NC, USA

Hi! I'm Darpan. 24 yr old Software Engineer, now pursuing Masters in Computer Science at NC State University, USA. This is my personal blog to share my interests in travelling, photography, programming and life. Glad to see you here, have a look around the website, you'll enjoy. Drop a comment or reach out to me or get connected via links below. Have a good day! :)

Subscribe to Newsletter
Countries Visited So Far: 7
– India
– Bhutan
– Philippines
– United States
– Thailand
– Bali, Indonesia
– Hong Kong
Latest Video
Subscribe YouTube Channel

Ads & Promotion

Please visit the advertisement/guest posts page for details regarding promotions.