Chicago’s Top Things to do

The Windy City is brimming with energy, culture, delectable cuisine, and stunning architecture.  I could have spent 48 days exploring this scenic and friendly Midwest epicenter…. but alas, 48 hours had to do this time! For those of you that want to experience the best of Chicago, but are limited on time, check out this itinerary that will ensure that you hit the highlights and have an authentic and memorable visit.

What better way to introduce yourself to Chicago than through a deep-dish pizza. Build up your appetite on that plane ride over, then have your taxi driver make a bee-line to Lou Malnati’s  in downtown Chicago  (the oldest family name in Chicago pizza!). I thought all pizza experiences were the same… that is until Lou Malnati’s slice of deep dish heaven! And don’t for a second feel guilty about all that “pie” you just ate… it’s all part of the authentic Chicago experience!

chicago top things to do

Where to Stay? 

Our pick is The Trump International Hotel & Towers is a true standout amongst all of the hotel offerings in the Windy City.  Location, location, location! This hotel’s location could not have been more primely perfect. From the moment of arrival, the attentive service levels and luxurious amenities stood out and exceeded all expectations. The beautiful suites are luxurious, yet simple and functional, the way hotel rooms should be designed.  My suite came with a full-functioning kitchen which was an added bonus – I loved feeling like I was staying in a condo or apartment instead of a hotel room.  Soaring above North Michigan Avenue, you couldn’t ask for better views of the city.  Request a room on one of the higher floors for even more stunning 180 degree views of the beautiful waterfront downtown area. Be sure to make time for the fabulous Spa!  The relaxation room is one-of-a-kind – how often can you relax before a spa treatment looking down on a beautiful urban landscape? Views are king in this high-level urban retreat that rivals any other 5-star spa I have experienced.

Trump.10 chicago top things to do chicago top things to do

Day Cruise! 

the famed Architecture River Cruise (take note that this is a seasonal activity – can’t take a cruise when the river is frozen!).  Architecture savants and newbies alike will gush at the beauty, diversity, and incredible history of the hundreds and hundreds of river-front edifices in Chicago.  There’s no better way to see them then by boat. If you’re really pressed for time, make this activity a priority – truly memorable, educational, and best of all, fun. Think American version of Paris’ bateaux-mouches!

chicago top things to do Chicago.boat cruise

Best Places to eat?

Back in downtown, you won’t want to miss the impeccably executed Italian food and chic city scene at RPM Kitchen (be sure to make a reservation in advance!). 

Chicago.RPM.1 chicago top things to do

What to Do? 

Make some time for the tourist-filled, but must-see Millenium Park.  Cloud Gate is the main attraction, but be sure to take some time to walk around and enjoy the rest of the park and all of it’s beautiful attractions.  End up at the Art Institute of Chicago to experience art that in my opinion is right on par with the Musee D’Orsay. An architectural gem filled with stunning works from all time periods (the Impressionist collection was a true highlight for me).  This museum can be enjoyed in 1 hour or 8 hours… there really is something for everyone here.

art institute millenium park

Pressed for time on your last day?

Hit up the John Hancock building and take elevator to the top floor for stunning 360 degree views of the city and the vast Lake Michigan, which I’ll admit, looked more like an ocean or sea to me! Then head to Wicker Park to see a neighborhood other than downtown that embodies all of the charm of Chicago in a more residential and low-key kind of way.  If you have time, duck into Hot Chocolate for a bite to eat and then take a stroll down Damen Avenue and pop into some of the fabulous boutiques.

Chicago.Hot Chocolate  Chicago.Hot 2

These 48 perfect hours in Chicago are guaranteed to leave you wanting more!

chicago top things to do 

By Karissa Hazy, is a freelance travel writer and consultant for Global Adventuress.

Acknowledgements:  We would like to thank Trump Hotel Chicago for hosting our stay.  All opinions expressed here are entirely our own.

Photo Credits:  some photos have been provided by websites from links in this article.



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