Exploring Chicago in Three Days

No matter when or what your travel style, Chicago is always a good idea. Even now in February. Yes it’s cold but yes, it’s still beautiful and so much fun. I am happy to share my favorite places and my newest discoveries. Chicago is one of the best food and cultural destinations in the U.S., and a place that has something for everyone, this city has truly captured my heart.

If you are looking for a great way to get to know Chicago, tours such as Chicago CityPASS and Chicago Explorer Pass are certainly options you should consider.

MILLENIUM PARK
Located right downtown, these gigantic parks provide a great place to hang out, have a picnic, or go for a run. You can also find people playing chess out here and during the summer they have a lot of free concerts. This is also where you will find the famous “Chicago Bean” sculpture.

Photo by @lindarose

Photo by @lindarose

CreditSandyNoto

BRUNCH AT SOMERSET

This restaurant is in the Gold Coast neighborhood and it surprised me how beautiful it is. It has really tall ceilings, art deco light fixtures - including a huge chandelier dominating the front room. To start we ordered the Gooey Butter Coffee Cake and it was SO good! After, I ordered the traditional Gold Coast breakfast with potatoes, scrambled eggs, bacon and toast. Everything was very very tasty.

LAKE FRONT TRAIL
Lake Front Trail is nearly 20 mile long recreational area that runs along Lake Michigan. A great place for a run or bike ride, the trail boasts beautiful views of the city and is a good option if you want to sightsee while getting in a workout at the same time. The trail runs near many of the most famed Chicago attractions. i’ve found this trail map to help you spot them.

Art Institute of Chicago by Jennifer Kathryn

Art Institute of Chicago by Jennifer Kathryn

ART INSTITUTE OF CHICAGO
Admission: General $25 / Illinois residents $23 / Chicago residents $20

Creative types and art lovers will want to spend days (if not more!) at the Art Institute of Chicago; the institute is world renowned for its collection. Though the museum is best known for its impressionist art, there are a variety of other art styles showcased as well. Don’t let the vastness of the museum overwhelm you—guided and self-guided tours are available every day and are a great way to see some of the museum’s best offerings.

CUPITOL COFFEE & EATERY
After all the walking and sightseeing, you’re going to need a break.Take a coffee break at the cozy Cupitol Coffee

DINNER AT BEACON TAVERN
Definitely make a reservation because this place gets busy. The lighting is low and the decor is swanky and kind of Great Gatsby-ish! I loved it. The staff is SUPER professional, and from the hostess to the waitstaff, everyone had great attention to detail. I ordered the crab cakes and it was very yummy! They’re also very well known for their cocktails - so go ahead and get one!

BREAKFAST AT GODDESS AND THE BAKER
Enjoy a warm cup of delicious coffee at Goddess and the Baker. The seating can be a problem if it is busy, but the service is fast and the space is warm and inviting. 

CHICAGO CULTURAL CENTER
Former site of the Chicago Public Library, this lovely building is known for its exquisite Tiffany mosaics, especially in its performance venue, Preston Bradley Hall. It has changing art exhibits.

360 CHICAGO
Admission: Adults $22 / Children $15 / Tilt Experience has an additional cost.

The former John Hancock Observatory is an observatory deck at the top of the John Hancock Center on Chicago’s Magnificent Mile. The observation deck is 1,000 feet off the ground overlooking the city and Lake Michigan. The observatory was included in the Travel+Leisure Magazine’s list of Top 10 Views in America. If you’re feeling adventurous and VERY brave, then you can also do the 360 Chicago Tilt. Eight visitors at a time stand on a platform which juts out and over the edge of the building. You stand facing a floor to ceiling glass wall and then the wall tilts downwards 30° so that the visitors can see not only out but directly down. I did it once…and it was terrifying but very worth it.

LUNCH AT THE HAMPTON SOCIAL
Just like the name suggests…they serve the kind of summery food you might also expect, like a watermelon and tomato salad, New England clam chowder, lobster rolls, and crab cakes.I didn’t know i loved Brussel sprouts until I tried them here! The beach and boat theme decor make Hampton Social aesthetically pleasing, and it’s a very enjoyable lunch spot.

LINCOLN PARK CONSERVATORY
The Lincoln Park Conservatory provides a welcomed respite from the fast pace of the city. Traveling to Chicago in the winter? Stop in to see palms and greenery even in the harshest of weather conditions. The conservatory has a variety of tropical plants, koi fish, and orchids to name a few. You don’t have to be a gardener or plant lover to enjoy the grounds. There is beauty at just about every turn at the conservatory making it a fun (and free!) stop on your tour of Chicago.

ENJOY DEEP-DISH PIZZA
Chicago developed the deep dish pizza, as well as the stuffed crust pizza, and no trip is complete without trying at least one. The deep dish pizza was invented by Pizzeria Uno, which is now a national restaurant chain. Many Chicagoans swear by Lou Malnati’s.

STROLL DOWN THE MAGNIFICENT MILE
This stretch along Michigan Avenue is known for its upscale designer boutiques. Even if you don’t want to spend money, it’s still an experience to stroll down the avenue and take in the sights, the people, and a look at the Chicago River.

Photo by Tim Trad

Photo by Tim Trad

WILLIS TOWER SKYDECK
Admission: Adults $25 / Children $17 (ages 3-11)
If you want a place to see the city from above then this is it. The Willis Tower offers you the Skydeck Experience with 360° views of the city. On a clear day you can see as far as four states - Illinois, Indiana, Michigan and Wisconsin. The tower has 110 floors and stands at 442 meters above the sidewalk; it is one of the tallest buildings in the world. 

FINE ARTS BUILDING

This ten story building is part of the Chicago’s Roosevelt University. It was designed for working artists and was completed in 1896 when it became an art institute and later an artists’ studio. Among the artists who have passed through these doors there has been Lorado Taft; William Denslow, illustrator of the Wizard of Oz; Frank Lloyd Wright rented a studio here in 1908 and Harriet Monroe, founder of Poetry Magazine. Today the building functions as a haven for artists with studios, recording studios, theaters, galleries and businesses related to the creative arts.

THE ROOKERY BUILDING
The Rookery Building is a historic landmark Chicago. The building was nicknamed after the many birds which would perch on the exterior walls and for the sneaky politicians who worked in City Hall which once stood on this plot

THE FIELD MUSEUM OF NATURAL HISTORY
This museum was built for the World’s Columbian Exposition of 1893, and to house its impressive biological and anthropological collections. Now the museum has 24 million objects, with everything from mummies, to gemstones, to dinosaur fossils.

HONORABLE MENTIONS

To summarize, in Chicago you’ll find world-class food, fun nightlife, lots of activities, and just a cool atmosphere. Visit in the summer when life on the lake comes alive. There’s not one person I know who doesn’t say, “You can’t get better than Chicago in the summer.”

I can’t wait to go back! What are your favorite spots in this amazing city?