Oak Park

Day Trips

Make the most of your day with our curated plans, packed with Oak Park's hidden gems and unique experiences!

day 1
Explore Oak Park
morning
:

Start your day with a visit to the Ernest Hemingway Birthplace Museum to learn about the author’s early life. Enjoy breakfast at a nearby cafe to fuel your adventures.

afternoon
:

Take a stroll through the Frank Lloyd Wright Home and Studio for an insight into the architect's innovative designs. Explore the surrounding area and have lunch at a local bistro.

evening
:

Dine at one of Oak Park's charming restaurants and savor delicious local cuisine. After dinner, consider catching a live performance at the Oak Park Festival Theatre.

day 2
Architectural Wonders
morning
:

Join an architectural walking tour to appreciate the stunning buildings designed by Frank Lloyd Wright. Stop by a coffee shop for a quick caffeine fix afterward.

afternoon
:

Visit the Unity Temple, another masterpiece by Frank Lloyd Wright, and enjoy its serene atmosphere. Grab lunch nearby, perhaps a sandwich from a deli.

evening
:

Relax in Scoville Park while enjoying a picnic dinner. Finish your day with a book from the Oak Park Public Library or catch a film at a local cinema.

day 3
Nature and Parks
morning
:

Begin your day with a refreshing walk at the Oak Park Conservatory to see diverse plant species. Don’t forget to capture some beautiful photos of the gardens!

afternoon
:

Have a light lunch at a café before heading to Austin Gardens for some outdoor fun. Enjoy activities like frisbee or simply relax and take in the natural beauty.

evening
:

Dinner at a trendy steakhouse awaits you, offering a cozy ambiance. Afterward, walk around downtown Oak Park and enjoy the nighttime scenery.

day 4
Arts and Culture
morning
:

Visit the Oak Park Art League to view local artwork and maybe even participate in a workshop. Breakfast at a nearby bakery will complement your creative morning.

afternoon
:

Explore the popular Oak Park Arts District, stopping into various galleries and unique shops. Enjoy a lunch break at one of the delightful restaurants in the area.

evening
:

Attend an art exhibit opening or community event if available. Have a casual dinner at a family-style restaurant and socialize with the locals.

day 5
Literary Adventures
morning
:

Start your day at the Oak Park Public Library, where you can browse through their vast collection of books. Enjoy a cozy breakfast at a nearby coffee shop after your literary excursion.

afternoon
:

Take a literary walking tour to see homes of famous authors who lived in the area. Between visits, find a charming spot for lunch and discuss your favorite reads.

evening
:

Dine at one of Oak Park's charming restaurants and savor delicious local cuisine. After dinner, consider catching a live performance at the Oak Park Festival Theatre.

day 6
Family Fun Day
morning
:

Kick off your family adventure with a visit to the Oak Park Children's Museum. The kids will enjoy interactive exhibits while you savor your morning coffee.

afternoon
:

Head to the nearby local park for a picnic lunch and some outdoor games. Let the children play at the playground while you relax in the shade.

evening
:

Visit a local ice cream shop for a sweet treat after dinner. Cap the day off with a family-friendly movie at a local theater or watch one at home.

day 7
Active Oak Park Day
morning
:

Rent bicycles and explore the scenic trails in and around Oak Park at your leisure. Enjoy a hearty breakfast to prepare for your day's adventure.

afternoon
:

Continue your bike ride to the nearby trails, stopping for lunch at an outdoor café. Take in the fresh air and beautiful scenery around you.

evening
:

Wind down your active day with a relaxing dinner at a local grill house. Afterward, enjoy a leisurely evening walk through one of Oak Park’s tranquil neighborhoods.

day 8
Oak Park Music Fest
morning
:

Grab breakfast at a local diner, then head to the Oak Park Conservatory for a peaceful start to your music-themed day. Take your time to enjoy the surroundings.

afternoon
:

Get ready for an afternoon of music performances at a local venue. Indulge in artisanal food from local vendors while you enjoy the show.

evening
:

Participate in an open mic night at a bar or café, showing off your own talents or supporting local artists. Finish with a comforting dinner at a nearby restaurant.

day 9
Shopping and Dining
morning
:

Begin your day with breakfast at a quaint café before heading to Oak Park’s shopping district. Explore unique boutiques and specialty stores.

afternoon
:

Refuel with lunch at a trendy restaurant after a satisfying shopping spree. Check out the local shops for artisanal goods and souvenirs.

evening
:

End your shopping day with a delightful dinner at a fine dining restaurant. If time permits, enjoy a gelato or dessert while strolling through the downtown area.

Discover Oak Park

Read more in our Oak Park 2024 Travel Guide.

Oak Park Travel Guide