72 Hours in Chicago the Windy City

In the words of Frank Sinatra “my kind of town, Chicago is.” Chicago, Illinois is one of those places where there’s so much to do, it’s difficult to know where to start. It’s a city with top-notch art and culture. It presents visitors with plenty of outdoor activities especially during the summer months. It’s a city with an eclectic array of cuisines and there’s also no shortage of entertainment options. 3 days in Chicago IL is nowhere near enough time to truly appreciate Chicago the Windy City, but it might be just enough to go through some of the city highlights.

Chicago the Windy City: Downtown Chicago from the L
Downtown Chicago from the L

72 Hours in Chicago the Windy City

Day 1: Getting Oriented

Start your trip by orienting yourself with Chicago the Windy City in Illinois. Hop on the “L” train and take it around Chicago’s central business district, the “Loop.” Most of the major tourist sites are located in this area including the Navy Pier, Grant Park, and the Art Institute of Chicago. When hunger strikes, head towards Lou Malnati’s Pizzeria and order the Malnati Chicago Classic deep-dish pizza. If you prefer to go meatless, try the “Lou”. This pizza institution has several dine-in locations but try to grab a table at the River North or South Loop location for additional seating.

3 Days in Chicago the Windy City: Chicago Deep Dish at Lou Malnati's Pizzeria
Chicago Deep Dish at Lou Malnati’s Pizzeria

Assuming you survived the hearty but delicious meal, walk some of it off along the banks of the Chicago River. The stroll will give you a good opportunity to view the incredibly diverse architecture of downtown Chicago. For dinner, try to score a reservation at Girl and the Goat. This popular casual yet hip restaurant headed by “Top Chef” winner Stephanie Izard serves New American cuisine infused with worldly flavors. Finally, end your first day by listening to live jazz at one of the historic Uptown bars like the Green Mill.

Chicago the Windy City: Lincoln Park
Lincoln Park

Day 2: Cultural Explosion

Experience the best of Chicago culture by spending the day at the Museum Campus. The area contains three of the best museums in the city dedicated to the natural sciences. They include the Field Museum, the Shedd Aquarium, and the Adler Planetarium. If you only have time for one, pick the Field Museum. The museum is infamous thanks to “Sue,” the most complete T-Rex skeleton ever found. There are also exhibits on mummies and a virtual display about the earth’s revolution.

3 Days in Chicago the Windy City: Sue, T-Rex Skeleton by Dave Mathis
Sue, T-Rex Skeleton by Dave Mathis CC 2.0

When you get a bit claustrophobic, head towards one of the lakeside parks, have a picnic, and then walk along the trails. If you’re feeling adventurous, cross the underground tunnel into Northerly Island for great views of Chicago the Windy City’s skyline, the harbor, and Soldier’s Field. After your outdoor escapade, explore Chinatown, one of the many ethnic neighborhoods in Chicago, and have dinner at the oldest Chinese restaurant in the neighborhood, Won Kow, before finishing the night off at the Chicago Symphony Center to listen and watch the Chicago Symphony Orchestra play well-known classical masterpieces.

The Art Institute of Chicago the Windy City
The Art Institute of Chicago

Day 3: Fun and Relaxation

Relax and have a bit of fun on your last full day in Chicago. Get some sun and sand on your feet at North Avenue Beach while watching sailboats glide along Lake Michigan. Then walk south and do a little shopping and sight seeing on the famous Magnificent Mile. The area is known primarily for its designer labels but there are also boutique shops selling anything from clothing to works of art. It’s also a great place to see some of the city’s most famous buildings, many of which are luxury Chicago hotels, designated landmarks and historic places.

3 Days in Chicago the Windy City: North Avenue Beach in Chicago
North Avenue Beach in Chicago

Continue your day at The Purple Pig, a wine bar right on the Magnificent Mile. Grab one of the outdoor patio tables, order a few plates of meat and cheese and wash it off with a glass of wine while watching people pass by. Then head off to dinner at The Italian Village’s Loop location where you’ll dine amidst whimsical décor that makes it seem like you’re in an Italian movie set. End the night with a performance by the Second City Improvisational Theater Company that will guarantee several laugh out loud moments. This half a century old comedy group has produced notable comedians including Tina Fey, Steve Carrell, Amy Poehler, Mike Myers, and Stephen Colbert.

To find out information about where to stay in Chicago including and a calendar of events to help you plan your 3 days in Chicago the Windy City, visit Choose Chicago, the city’s official tourism website.

About Iris A

Website: http://www.travelingwithiris.com

Born in the Philippines, but grew up in Texas, Iris has been traveling and writing about her experiences for well over a decade. Her work has been published on well-known travel sites like Hipmunk (#hipmunkcitylove) and D Magazine Online Travel Club. She has been all over Europe, the US, and has recently started exploring Latin America. She loves trying local cuisine and visiting UNESCO deemed World Heritage sites. Her favourite city is New York, with London, following a close 2nd. You can follow her on Twitter @sundeeiris or through her travel blog, Traveling With Iris.

Other posts by the Author

One Response

  1. Best American Midwest Winter Getaways | Go 4 Travel Blog

    […] Chicago is the perfect spot for those who prefer the buzzing city energy to the great outdoors. There is literally no excuse why you can’t find anything do here in the Windy City. Though Chicago has gained worldwide attention for its Chicago-style hot dogs and deep dish pizzas, the city has a ton of more delicious options to offer, thanks to its diverse population. Chicago may not be a particularly glamorous city; however, the tons of neighborhoods within the city limits contribute to the city’s unique personality. […]


Leave a Reply