One of Chicago’s classic gems, the zoo is completely free to visit and open every day from 10 AM to 5 PM. It’s an easy spot to stroll and see the animals. Parking is limited, recommend walking or planning transport.

Visit the 103rd floor of Sears Tower for some of the best views in the city. Tickets are around $30 to $40, and it’s open daily from morning until late evening. Perfect for a daytime, sunset or nighttime visit.

Chicago’s legendary comedy club where so many SNL stars got their start. Shows run most evenings, tickets usually range $30 to $50. Recommend reserving tickets ahead of your visit.

Home to world famous pieces like A Sunday Afternoon on the Island of La Grande Jatte and Monet’s Water Lilies, the museum is a must see for art lovers. General admission is around $32 and it’s open daily from 11 AM to 5 PM. The café and outdoor gardens are a beautiful stop during a summer visit.

A short walk from the lakefront, the Museum of Contemporary Art showcases bold modern art from living artists across the globe. Tickets are about $19, it’s open Tuesday through Sunday, and the rooftop terrace is a hidden gem with a beautiful view of the lakefront.

A classic way to see the city. These 90 minute cruises glide past iconic Chicago buildings while guides share the city’s history and architectural context. Tickets are usually $40 to $50, boats run daily, and most tours depart right along the riverwalk downtown.

Right in the heart of downtown, this is where you’ll find The Bean, outdoor art installations, and often free concerts or events at the pavilion. The park is open daily and free to visit, making it an easy stop before or after exploring nearby Buckingham Fountain, Lakefront Trail or the Art Institute.

Stretching along Lake Michigan, the 18.5 mile trail is perfect for a morning jog, bike ride, or a scenic walk with skyline views. Grant Park sits right along the trail (home to Buckingham Fountain) and it's right next to Millennium Park, both are free and open daily.

One of the largest and most beautiful conservatories in the country, opened to the public in 1908. It’s like stepping into a lush tropical garden right in Chicago. Located right off the green line (Conservatory-Garfield station) and has ample free parking, admission is free (donations encouraged), and it’s open daily.

Tucked away in Lincoln Park, this hidden spot is a great break from the city filled with winding paths, a waterfall, and of course lilies. It’s free to visit, perfect for a peaceful stroll before or after the zoo.

Right off Montrose Harbor and beach, this lakefront spot is a haven for birdwatchers and one of the most peaceful places in the city (home to the endangered piping plover!). Open year round with both paid and limited free parking. Especially pretty at sunrise with views of both nature and the skyline!

An old elevated rail line turned into a 2.7 mile walking and biking trail. The 606 winds through Chicago’s neighborhoods with street art, parks, and skyline views. It’s open daily, free, and perfect for a casual stroll or bike ride!

Jackson Park is a huge green space with lagoons, gardens, and trails right off of the lakefront trail. It’s free to explore and open daily, and it’s also home to the Museum of Science and Industry.

Located in Pilsen, this museum showcases 3,600 years of creativity from both sides of the border, exemplifying the diversity of Mexican culture. Admission is free, and it’s open Tuesday through Sunday, great opportunity to see one of the largest collections of Mexican art in the US.

The Shedd Aquarium is home to beluga whales, penguins, and thousands of other aquatic creatures. It also doubles as Evan's second home! Tickets are about $40, and it’s open daily from morning until early evening. Parking is available, but fills up quickly as the weekends get busy!

A stunning historic building downtown, opened to the public in 1897 originally. This was the country's first free municipal cultural center; best known for the world's largest 40ft Tiffany stained glass dome. Admission is always free, and it’s open daily with art exhibits, concerts, and events!

A serene modern study in River North, the Poetry Foundation offers a free library, gallery, and quiet garden dedicated to celebrating poetry. It’s open Tuesday through Saturday, and worth a visit if you’re looking for a peaceful break from the city!

Once an abandoned bank, this landmark has been transformed into a stunning arts and cultural space curated by artist Theaster Gates. Open Thursday through Sunday with free admission, it has everything from rare vinyl collections to archival books in a beautiful historical space.

Amelia’s go to doughnut spot in Lincoln Park, serving creative vegan doughnuts. It’s a walk up window down an alley, cashless, and sells out quick. Highly recommend pre ordering online ahead of the weekend for pick up!

A Ukrainian Village diner famous for its Filipino breakfast. It’s cash only, usually under $15 a plate, and offers unforgettable Longanisa, tocino, and garlic rice. Most often the wait is an hour, just enough time to visit Dark Matter Coffee across the street.

A Chicago institution since 1923, this classic diner near Union Station is right at the start of Route 66. Known for hearty breakfasts and free donuts with every meal. Often has a line, but tables have a fast turn over(no reservations or lists, just hop in the line!). It’s casual, affordable, and perfect for fueling up before a day of exploring the city.

A cozy Little Italy spot right down the street from Amelia and Evan, Sweet Maple is known for its southern comfort food. You can't go wrong from cinnamon roll pancakes, house made biscuits, or hand squeezed OJ. Most plates under $20 and has street parking. Usually has a bit of a wait, but the line moves fast!

A Michelin starred gem in East Village, Kasama serves modern Filipino food. Casual bakery by day with incredible pastries, and a fine dining tasting menu at night. Expect a very long line in the morning, recommend getting there before they open if you're wanting to dine in(no reservations for breakfast, can skip the line by ordering pick up). Reservations required for dinner, recommend reserving your table online before your trip since they book up fast!

A family run Italian deli in the West Loop, J.P. Graziano’s is famous for stacked subs on fresh bread. Perfect for a quick and classic Chicago lunch, with the option to add giardiniera on any sub! Most sandwiches are under $15, and every sub can be made as a salad. It’s open weekdays and Saturdays (closed Sundays).

A favorite spot in Lincoln Park serving handmade dumplings, noodles, and homestyle Chinese dishes. It’s casual, affordable (most plates under $15), and BYOB. They don't take reservations, but have a list to add your name. Perfect for a cozy group dinner!

Located in Chinatown, QXY is famous for its handmade dumplings (boiled, pan fried, or steamed). Recommend trying one of each (can't go wrong with any of the filling options!) paired with their Jasmine Tea. Most dishes run $10 to $15, and it’s open daily for lunch and dinner. They don't take reservations, recommend joining the waitlist while you explore Chinatown Square!

Evan’s (and the rest of the country's) favorite deep dish. Pequod’s is legendary for its caramelized crust and iconic cheese pull. Pizzas run about $25 to $30 and are best shared. Just be ready for a bit of a wait, would recommend making reservations especially for larger parties!

A favorite authentic Mexican steakhouse where everything is cooked over an open flame. Their skewers are a must get, with massive platters of grilled meats, veggies, and fresh tortillas. It’s BYOB, cash only, and has paid street parking. They don't take reservations, recommend putting your name in while you explore the Pilsen shops!

In Pilsen, HaiSous serves beautifully crafted Vietnamese dishes that balance tradition with a modern twist. Highly recommend the signature Whole Fried Fluke and Vegetarian Curry, but everything on the menu is incredible! Entrées are usually $20 to $30, and it’s a great spot for a beautifully curated dinner. Highly recommend reserving your table online before your trip since they book up fast, paid street parking is available!

A favorite spot in Hyde Park, Virtue brings Southern flavors with a modern twist. With James Beard Awarded chief's all the food is amazing, our favorites are their shrimp and grits, blackened catfish, and fried green tomatoes. Entrées are around $20 to $35, and recommend booking your table before your visit. Right off Lake Shore Drive with street parking available, this is a perfect easy to get to spot for comfort food and a welcoming atmosphere!

A Chicago classic since 1921, Margie’s is all about old school charm. With massive sharable sundaes, house made chocolates, and classic dinner vibes, it's a dream spot for anyone with a sweet tooth! It’s cash only, open late most nights, street parking outside is limited(parking is available in the area, plan for a little bit of a walk!)

Amelia's favorite ice cream shop in Wicker Park, Vaca’s house made soft serve and toppings happen to be 100% vegan. Highly recommend the Affogato or Death by Chocolate Sunday's. Cups and cones are usually under $7, and it’s open afternoons and evenings. Street parking is available but limited!