Things To Do
Small Cheval- Hyde Park
Come to our neighborhood for a burger and ice cream! Small Cheval has several locations throughout the city, but this is the one we frequent the most, 1 block from where Jacob lived for several years. It's so good, and also what we picked up for our engagement picnic 🥹 If you're gluten free (like Katie is), you're in luck! They have a great gf burger bun 👌🏼
Harold's Chicken Hyde Park
Harold's fried chicken, you gotta have it 🔥 There are lots of different locations in the city and they're not all equal. Hyde Park location is 👌🏼 Order with lemon pepper and mild sauce, a Chicago staple. Keep in mind that they serve whole wings, so a 3-piece is essentially a 6-piece!
Bueno Days
THE BEST COFFEE SHOP IN CHICAGO!! And we're not the only ones who think so. This place is SO near & dear to our heart (especially Katie's) 🥹 Like, we thought about shooting our engagement pictures here 🥹 Bueno Days is located in the historically Mexican Little Village neighborhood, where Katie lived for her first 6 years in Chicago, so this is close to home. Katie is a regular here and baristas know her name, which has been a lifelong dream 😂 Order the momo matcha, or the confleis, or a cardamom latte, or....literally anything on the menu.
La Chaparrita Taqueria
While you're in Little Village, you might as well stop for some tacos, and the ones in this neighborhood grocery spot are 🔥🔥🔥 Order al pastor and asada. Katie also loves the tripa, fried hard 👌🏼
Jim's Original
An iconic Chicago hot dog stand!! They've been here since 1939 and claim to have created the original Maxwell Street polish. Order the polish with extra grilled onions 👌🏼
Chicago's Home of Chicken & Waffles
A Bronzeville spot for soul food, most notably their chicken & waffles!
Stax Cafe
A solid breakfast spot! We've come here often and it's just always good and has a great neighborhood vibe. If you're like Katie and are gluten free, they have gf pancakes!
MCCB Chicago
Excellent Chinese food in the heart of Chinatown! This place has a Michelin star.
Hing Kee
A great place for soup dumplings in Chinatown!
Au Cheval
Au Cheval is famous for having the best burger in the city (sure, this is debated, but trust us). Small Cheval is their fast casual branch, but this is the OG spot where it all started. Their food is definitely more $$ but it's worth it, in our opinion. Everything is GOOD!! Jacob says to ball out and add the fried egg AND the bacon to your burger. Fair warning though: there are no reservations, and the wait is typically 1-2 hours....but worth it!! We would recommend putting your name in and then walking around and exploring the shops/bars/etc. in West Loop/Fulton Market until they call you. Have fun!
MONEYGUN
This is a West Loop/Fulton Market spot (waiting for Au Cheval? This could be a good option!) We've stopped here several times for a drink & to enjoy some rap/R&B and the vibes & drinks are always solid. They also have a photobooth which we always love 📸 Check it out!
Do-Rite Donuts & Chicken
Need a sweet treat? 🍩 There are several spots throughout the city, but this West Loop location is where we go most (they also have great chicken strips). This West Loop/Fulton Market area is *busy* but also has lots of trendy shops & food spots.
Downstate Donuts
These donuts are a little further north in Chicago than where we typically spend our time, but we have come here on Saturday mornings right when they open for some fresh, delicious donuts. They use potatoes in their recipe and...it really works! Texture is a cross between a yeast donut and a cake donut.
Good Ambler
Where we went on our first date 🥹 This is a West Loop/Fulton Market coffee shop w/ lots of pastries. We actually didn't end up sitting in here on that 1st date because it gets busy, so we got coffee to go and walked around the area. It was actually more like power-walking until Jacob finally spotted a bench and asked to pause and rest 😂
Queen Mary
Another fun spot for drinks! This is located in the Ukranian Village neighborhood (near Wicker Park) and has a cool maritime themed interior and great drinks. They also have an oyster bar sometimes!
sweetgreen - Healthy Salads, Bowls and Plates
This is a chain and there are locations all over Chicago, but if you're like please I need to eat something with vegetables, sweetgreen is always solid! Jacob's order is the Harvest Bowl, Katie's is either the Crispy Rice OR the Harvest Bowl OR the Buffalo Chicken bowl.
CAVA
CAVA is new to Chicago and it's another lighter/healthier option but still GOOD. Come here for mediterranean style bowls! If you do the Wicker Park location, you'll be on Milwaukee Avenue which is full of shopping (several vintage thrift stories) and some bars & coffee shops too.
kibbitznest books, brews & blarney
A place to play boardgames of all kinds while sipping your drink of choice (there's a bar and also some food and coffee options). To be honest, we've actually never been here...but have always wanted to go and have heard great things! Another place that does a similar thing is Snakes & Ladders!
The Art Institute of Chicago
We love art museums, and Chicago does it WELL. Check out the Thorne rooms in the basement (look it up)!
Shedd Aquarium
Your chance to see some beluga whales! And jellyfish!
Garfield Park Conservatory
This is where we had our engagement pictures taken! It's BEAUTIFUL. Hopefully the weather is nice while you're in town but if not...this is a great way of getting "outside" and feeling like you're someplace warm and nice :)
Burnham Park Promontory Point
A peninsula on Lake Michigan in the Hyde Park neighborhood that gives really pretty views of the city and lets you walk right along the lake! We've enjoyed many many walks here. There are plenty of grassy spots, benches, and rocky areas to linger at too if the weather is nice!
Stop By the Obamas' House?
If you're in Hyde Park, might as well drive/walk by the Obamas?? You can't drive onto their street, but you can park nearby and walk through. Their house is heavily monitored by secret service so don't *linger* but it's cool to walk by.