After almost 5 years of being in Chicago, I have a pretty good handle on what’s fun and worthwhile seeing in this city; and what’s not. There are a lot of touristy activities to do in the city, that shouldn’t be overlooked. The bean, Navy Pier, ‘Sears’ tower, (or whatever people are calling it these days) are all fun.
However, if you’re wanting to experience the Windy City as a true Chicagoan, LISTEN UP!
I have a day planned out for you full of fun, delicious eats, and great sightseeing. You don’t have to shop all day on Michigan Ave or go up in the tallest buildings to experience the best of Chicago.
Next time you’re in Chicago and done being a tourist, check out my itinerary for NOT being a tourist for one day in this amazing city:
Early Morning – Stroll in Olive Park
Millennium Park is cool and all, but if you want to experience a different scene then go for a stroll and watch the sunrise at Olive Park. Olive Park is accessible by Navy Pier, and it’s a hidden gem that not many tourists know about. There’s a tree lined paths that offer breathtaking views of the skyscrapers right along Lake Michigan. And you can continue your brisk walk along the Lakeshore path.
There’s even a ledge that shoots out over the lake to capture some awesome pictures. You’re going to be doing a lot of eating in Chicago, so you may as well exercise in the morning!
Morning – Brunch in West Loop
After your stroll, shower up, get ready and head to the West Loop neighborhood for a lovely brunch! I’m sure you worked up an appetite. West Loop is located just west of the downtown area (obvs) and is super accessible by cab or Uber. If you’re staying in the Loop or River North, the drive is less than 10 minutes.
West Loop is a neighborhood filled with delectable food. If you consider yourself a ‘foodie,’ you can’t visit Chicago and not visit West Loop. The variety is incredible!
My favorite meal is brunch. I’ve recently been venturing out of my neighborhood and heading over to the West Loop to indulge in egg benedicts and mimosas. Some of my favorite restaurants in West Loop for brunch are Noosh & Booze and Bad Hunter.
Afternoon – Walk the Riverwalk
So now that we have you all full on food, it’s time to walk it out.. again. That’s really all I do in Chicago – walk and eat. Eat and walk.
The riverwalk offers different views of the city, and a great perspective of all the high rises. They recently expanded the riverwalk, and it seems to go on forever! They also put in bars and restaurants along the river, which is super convenient when you’re ready for a cool-down cocktail.
They often do special events and art exhibitions, so be sure to check out if anything’s available during your stay. This may seem like a tourist trap, but a lot of it is brand new and worth a visit!
Late Afternoon – Check out the Cultural Center
You can get off the riverwalk at Michigan Ave and stroll down to the Cultural Center. Why do I recommend this over the Field Museum, the Shedd or the Museum of Contemporary Art? Because it’s FREE! It’s a stunning building on the inside. The detail and work that went into the stained glass domes is just amazing. I could stare into that ceiling forever.
They often offer art exhibits, music, lectures, theater and dance events, and more. After living here for 5 years, my first visit to the Cultural Center was only a few weeks ago. I barely hear anything about it – so definitely put it on your list!
Evening – Find the Best Sushi
Ahhh, sushi. SO many delicious sushi restaurants in Chicago. It couldn’t be more opposite than the famed deep dish pizza, but Chicago has many sushi restaurants to boast about in all their neighborhoods.
I’ve already written a handful of posts about sushi in Chicago, so take a look at my reviews and take your pick! You really can’t go wrong with any of these places:
Juno Sushi in Lincoln Park
Momotaro in West Loop
Jellyfish in Gold Coast
Seadog Sushi in Wicker Park
Late Night – Karaoke in Chinatown
Who doesn’t have fun karaoking? Sakura Karaoke Bar in Chicago’s Chinatown neighborhood does it right. They have a fully stocked bar, and private room for you and all your friends if you’re too embarrassed to get up in front of strangers.
We did this for a friends birthday party, and everyone had a blast. Be sure to rent your private party room ahead of time. It’s the perfect ending to what’s probably an already memorable trip!
Now that’s a fun, full day in Chicago. This day guide will take you across some different neighbors and avoid the major tourist traps. Chicago is such a walkable city, you can really go with no plans and run into some amazing things!
Do you have any recommendations I missed for being a non-tourist in the Windy City? Comment below!