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Chicago Things To Do
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items There is no place I'd rather live than right here in Chicago. While making lists of all the places I love is impossible (there are just too many!), here are some of my faves.
Sections
5
Outdoor Activities
Restaurants
Other Food & Drinks
Arts & Entertainment
Local Favorites
Outdoor Activities
This is a beautiful park with so much to explore! I like to come here for a run and incorporate the stairs and ramps to get some elevation. The wildflowers are abundant, and the view of the city from the top of the hill is wonderful.
Palmisano Park
There is always something to do at Millennium Park! In the summer they have Movies in the Park (and it's BYO food and alcohol!), and in the winter there is ice skating. There are too many activities to list here, so definitely check it out for yourse...
Millennium Park
This a lovely area with a hidden gem of a restaurant: Boat Drinks. Located right on the water, the view can't be beat. They have literally THE BEST Mahi Mahi sandwich I've had anywhere in the city. The prices are reasonable; it's like being at a neig...
Burnham Harbors
This is a beautiful little state park - perfect for just a weekend camping trip. We went in October, and the colors were magnificent. Galena is just a short drive away, so it's very easy to head to town for lunch.
Apple River Canyon State Park
This is a fabulous place to catch a concert! My favorite venue in the city. You can also walk or run through it when there isn't an event and enjoy the views.
Huntington Bank Pavilion at Northerly Island
Really nice small farmer's market with a good variety of vendors. There's a produce vendor here every year that is top-notch, along with Stamper Cheese which is divine.
Chicago Nettelhorst Fre…
This beautiful trail is an easy hike and just a short drive from the city. The waterfall is well worth it.
Waterfall Glen Forest Preserve
This place is spectacular! While it is perfect for visiting any time, it’s even better during the winter when you need some plant love. Go on a sunny day, and you will instantly get rid of your winter blues. Free for Chicago residents and only a mini...
Garfield Park Conservatory
The Botanic Gardens is one of my favorite places to be, which is why I renew my membership every year. There are beautiful things to see no matter what season it is. It is a trek out of the city, but you can take a Metra train directly to it. (Inside...
Chicago Botanic Garden
Chicago has amazing architecture, and one of the best ways to experience it is on a boat tour. Be prepared for beautiful views and to learn more about the history of our beautiful city.
Chicago Architecture Center River Cruise aboard First Lady
Restaurants
My restaurant list isn’t going to be the same “must eats” that are on many of the touristy/influencer sites. This list consists of places where I just love to go for a great meal, excellent service, and an overall enjoyable time out.
One of my favorite restaurants and a must if you enjoy Filipino food. Owned and operated by my good friend Kathy, you can feel the love she puts into her cooking. I’ve had everything on the menu, and it’s all delicious. I brought my mom (who was born...
A Taste of the Philippines
We LOVE this place! I’m a runner, and this is one of my favorite carb-loading spots in the city. Everything is delicious. Sit at the bar with Kyle because she’s a true gem, and tell her I sent you.
PR Italian Bistro
This is such a wonderful family-owned place. Not only do they have excellent food, but they are active members of the local community. You can also find live entertainment here, so be sure to check their website.
Mrs. Murphy and Sons Irish Bistro
Now THIS is the place Chicagoans crave when in the mood for deep dish. It’s only a short taxi/Uber ride from the downtown area and totally worth the trip.
Fun fact: Chicagoans are actually alllll about their tavern style pizza. We don’t actually eat...
Pequod's Pizza
If you’re visiting the Andersonville neighborhood, you simply must check this place out. Order the molé - you won’t be disappointed.
Los Arcos
Okay, so this place is part of chain, but I needed to include it because we just love coming here. It is one of the most beautiful restaurants I’ve ever been in, and the food is delicious. Perfect for a special occasion or grab a seat at the bar for ...
TAO Chicago
I love, love, love this little cafe! The food is delicious, they have plenty of gluten-free options, and they have alcohol. They actually have one of the most delicious espresso martinis ever, AND it’s available in decaf.
Pick Me Up Cafe
Other Food & Drinks
Okay, so full disclaimer - I work here to supplement my income as a solopreneur life coach. Life coach/bartender - it’s a good pairing as they both require a lot of the same people skills.
However! I got this job because this was my favorite place ...
Mom's Place - A Chicago Gathering Spot
Cindy’s has the best view! In the fall they have fire pits out on the patio to keep it cozy. Reservations are recommended during busy times (and especially if you want a table) but you can usually walk-in, grab a drink from the bar, and head out to t...
Cindy's Rooftop
This is such a fun, one-of-kind spot in the River North neighborhood. While they specialize in rum cocktails, they do have cocktails with other liquors available. The tiki bar vibes just shouldn’t be missed, so walk down that alley and grab a drink. ...
Three Dots and a Dash
Arts & Entertainment
Okay, so full disclaimer - I work here to supplement my income as a solopreneur life coach. Life coach/bartender - it’s a good pairing as they both require a lot of the same people skills.
However! I got this job because this was my favorite place ...
Mom's Place Chicago
The Art Institute is my favorite museum in the city. I never get tired of visiting, which is why I have an annual membership. In addition to a spectacular permanent collection, they always have rotating/temporary exhibits that bring in art from all o...
The Art Institute of Chicago: Home
This hidden gem is located just a short walk away from the Magnificent Mile. It is a book lover/poetic soul’s dream, and best of all it’s FREE!
Poetry Foundation
Redhead’s is a Chicago institution and a definite must if you are into live music and good people-watching.
Redhead Piano Bar
During the time I didn’t live in Chicago, this is one of the places I made sure to go every time I came home for a visit. With two stages and iconic blues players, you will experience the best Chicago has to offer. Open until 4am, so no excuse to not...
Kingston Mines
Local Favorites
Almost everyone coming to Chicago asks about deep dish. While the most common answers you’ll hear in the downtown area is either Giordano’s or Lou Malnati’s, those of us who live here know to take a taxi out to Pequod’s. Their caramelized crust is wo...
Pequod's Pizza
If you’re heading to Wrigley and want a local bar instead of the corporate spots that have popped up all along Clark St, swing by Jaqueline’s. Close enough to the ball park to walk but far enough away that you’ll have mostly people from the neighborh...
Jacqueline's - Dive Bars - Yelp
Murphy’s will always have my heart. When the Cubs were chasing the World Series in 2016, Murphy’s was one of the only bars in Wrigley that didn’t charge a ridiculous cover charge to enter. While the corporates, and even some of the local spots, were ...
Murphy's Bleachers Home - Murphy's Bleachers - Chicago's ...
Ping Pong is one of my all-time favorite Chinese restaurants. With its 40s decor and delicious food, you can’t go wrong coming here.
Pingpong