2 Days in Oak Park: The Best 48 Hours Unlocked

If you are spending 2 days in Oak Park and need an itinerary from a local, you are in the right place.

Just outside of Chicago, the charming suburb of Oak Park offers the perfect weekend escape. Known for its beautiful Victorian architecture and as the hometown of famous author Ernest Hemingway, Oak Park provides a quaint small-town atmosphere that is just a short train ride from the city.

For those looking to explore this historic village over a 2-day visit, Oak Park makes it easy with walkable streets full of shops, restaurants, and cultural attractions.

In this blog post, I’ll provide an insider’s guide to experiencing the best of Oak Park in 2 days. I’ll share my recommended itinerary for how to see the highlights and hidden gems, where to stay, tips for getting around, and the food and entertainment that capture the essence of this delightful town that feels worlds away from city life.

Whether you’re a first-timer or a return visitor, get ready to fall in love with Oak Park as we uncover the best ways to spend 2 days in this charming town. There are some hidden gems and great spots for buying souvenirs.

Itinerary: 2 Days in Oak Park

Day 1: Exploring Historic Oak Park

Morning:

Breakfast at the Chicago Waffles: Start your day with a delicious breakfast at one of the newest Oak Park restaurants. This cozy spot offers a variety of breakfast options, from omelets to pancakes, and epic waffles! 

📍726 Lake St | Opens daily at 7:00 AM

Visit the Frank Lloyd Wright Home and Studio: Begin your exploration of Oak Park’s rich architectural heritage with a guided tour of the Frank Lloyd Wright Home and Studio. Learn about the early career of the famous architect, Frank Lloyd Wright houses in Oak Park, where he lived, and where he worked.

📍951 Chicago Ave | Opens daily from 10:00 AM to 4:00 PM

Midday:

Lunch at Amerikas: Head to Amerikas for a Latin-inspired lunch. Their outdoor seating is perfect for a relaxing meal. Don’t miss their guacamole and delicious stuffed taquitos.

📍734 Lake St | Opens daily at 9:00 AM to 2:30 PM; and 4:00 PM to 8:00 PM

Explore the Hemingway District: After lunch, take a stroll and head south on Oak Park Avenue through the Hemingway District. Visit the Ernest Hemingway Birthplace Museum to learn about the famous author’s life and work. The district is also home to charming shops and boutiques.

📍339 N Oak Park Ave | Opens at 1:00 PM (Th, Fr, Su) and 10:00 on Sat

Afternoon:

Pleasant Home: Visit Pleasant Home, an architectural gem designed by George W. Maher. Take a guided tour to admire the stunning interiors, and the gardens, and learn about its history.

📍217 Home Ave | Opens 11:00 AM to 4:00 PM on Thursday

Relax in Mills Park: Explore the natural beauty adjacent to Pleasant Home. This is a hidden gem in Oak Park where you can enjoy a stroll through the park’s lush greenery and towering trees. It’s perfect for a morning or afternoon walk and take in the tranquil surroundings. If you’re traveling with kids, let them enjoy the playground equipment and open spaces for a delightful family outing.

📍217 Home Ave (next to Pleasant Home)

Evening:

Dinner at Lou Malnati’s: Enjoy dinner at one of the best restaurants in the area for a pan of deep-dish pizza.

📍1038 Lake St | Opens daily at 11:00 AM

Live Performance (seasonal): If your visit falls during the summer months, check out the Oak Park Festival Theatre for a Shakespearean play or other live performances in Austin Gardens.

📍167 Forest Ave

Related article: Our Guide to the Best Summer Events in Oak Park will hold your passport to having outdoor fun. 

frank lloyd wright home and studio

Day 2: Arts, Culture, and Nature

Morning:

Breakfast at Cozy Corner: Start your second day with breakfast at a spot that locals love. This neighborhood restaurant offers tasty breakfast options, including chilaquiles.

📍138 N Marion St | Open daily from 7:00 AM to 3:00 PM

Explore the Oak Park Conservatory: After lunch, visit the Oak Park Conservatory. This lush greenhouse features a wide variety of plants and is a peaceful spot to explore.

📍615 Garfield St | Open daily from 10:00 AM to 4:00 PM; closed on Monday

Morning:

Breakfast at Cozy Corner: Start your second day with breakfast at a spot that locals love. This neighborhood restaurant offers tasty breakfast options, including chilaquiles.

📍138 N Marion St | Open daily from 7:00 AM to 3:00 PM

Explore the Oak Park Conservatory: After lunch, visit the Oak Park Conservatory. This lush greenhouse features a wide variety of plants and is a peaceful spot to explore.

📍615 Garfield St | Open daily from 10:00 AM to 4:00 PM; closed on Monday

Midday:

Lunch at Poor Phil’s: Pick up some sandwiches or salads from this local pub and enjoy a cold brew. A beautiful nearby park (next to Pleasant Home) is a great place to relax if you order a take-away for a picnic.

📍139 S Marion St | Opens daily at 11:00 AM

Visit the Oak Park Art League: Explore the local art scene at the Oak Park Art League. They often feature exhibitions of contemporary and local artists. 

📍720 Oak Park Ave | Open at 1:00 PM, closed Sun and Mon

Afternoon:

Shopping: Spend some time shopping in any of these neighborhoods. You’ll find boutique shops, bookstores, and more.

  • Marion: On Marion Street and Lake Streets
  • Downtown: Oak Park Avenue and Lake Streets
  • Harrison Arts District on Harrison between Ridgeland and Austin Streets. 

Unity Temple: Visit Unity Temple, another iconic Frank Lloyd Wright creation. While tours of the interior are limited, you can still admire its distinctive exterior design.

📍875 Lake St | Open at 10 Mon-Fri, 9 AM on Sat; closed Sun

Evening:

Dinner at Cucina Paradiso: Enjoy a leisurely dinner at Cucina Paradiso, known for its Italian cuisine and craft cocktails.

📍814 North Blvd | Opens daily at 5:00 PM

Live Music at Fitzgerald’s Nightclub: If you’re in the mood for live music, head to Fitzgerald’s Nightclub. This historic venue often hosts local and touring bands across various genres.

📍6615 Roosevelt Rd, Berwyn | Open daily except Mon

Final Thoughts on a 2 Days in Oak Park

After writing this itinerary based on my own experiences in Oak Park, I think you’ll fall for the charm and appeal of this historic village.

From Ernest Hemingway’s birthplace to the plethora of independent shops and eateries, Oak Park offers the perfect blend of culture, architecture, and community just outside Chicago.

With great walkability and transit access, it’s easy to pack many highlights into a weekend visit. Whether strolling under the canopy of trees, admiring Frank Lloyd Wright designs, or sampling craft brews and cuisine from award-winning restaurants, Oak Park has something delightful around every corner.

The next time you find yourself with a free weekend, consider an escape to this inviting suburb for a memorable and accessible getaway.

After just 2 days in Oak Park, you’re sure to feel like a local ready to return soon!

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