A classic Chicago breakfast diner known for hearty plates and pancakes.
Award winning bakery and café, often considered one of the best bakeries on the West Side of Chicago.
Steps away from Hannah & Jon's old apartment. Established in 1921, Margie's has the best ice cream in the city. Hannah's order is a chocolate marshmallow malt. Jon's order is blueberry or pistachio flavored ice cream in a waffle cone.
A famous Chicago donut spot with a wide variety of creative flavors.
Beloved for its biscuits and pies. Sells out frequently, so arrive early. Must haves include the Chicken Pot Pie, Gravy Biscuit, and the massive Chocolate Chip Cookie.
Hannah and Jon’s favorite burger and cocktail spot. The side of Mac N Cheese and Fries with sweet & spicy aioli are to die for!
Arguably the best burger in the city (add the bacon, its worth it!). Expect long wait times (1 hour+), but there is plenty to explore nearby on Randolph street.
Au Cheval’s little sibling. A faster option that still delivers an excellent burger.
Widely recognized as the best deep dish pizza in Chicago. This is Hannah's favorite deep dish pepperoni pizza!
Laid back neighborhood spot with a great patio, burgers, and pizza. Jon and Hannah's favorites include the "All The Right Moves" pizza, the garlic knots, and the "Stop-In" Burger.
Mexican restaurant known for tacos, margaritas, and a fun atmosphere. Hannah strongly encouraged Jon to split a pitcher of margaritas with her the day before his Half Marathon. Jon couldn't say no because they are THAT good!
Jon never had a Steak Burrito from here that he didn't like.
Enjoy a walk or bike ride (rented through lyft) along this 2.7 mile elevated multi use trail and park that winds through several Chicago neighborhoods. There are multiple access points near the hotel, making it an easy and scenic way to explore the city.
Head to downtown Chicago to stroll along the river and take in the city’s iconic architecture. The Riverwalk is lined with restaurants and bars, perfect for grabbing a drink, enjoying a meal, or simply soaking in the views. Hannah and Jon had their first date on the Riverwalk in July 2021 and it's also where they got engaged in August 2024!
Home to the Bean, plus gardens and open green space. An easy stop if you are already in the Chicago Loop.
A scenic path along Lake Michigan that is perfect for walking, running, or biking, with incredible skyline and lake views.