Oakbrook

Day Trips

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

day 1
Arrival and Orientation
morning
:

Arrive in Oakbrook and settle into your hotel. Spend the morning exploring the immediate area, getting a feel for the local culture and surroundings. Stop by a local café to enjoy a hearty breakfast while planning your itinerary.

afternoon
:

Visit the Oakbrook Center, a premier outdoor shopping destination, where you can browse luxury boutiques and dine at fine restaurants. Take a leisurely stroll through the beautifully landscaped grounds, enjoying the vibrant atmosphere. Grab a quick lunch at one of the charming eateries within the center.

evening
:

Enjoy a relaxed dinner at one of Oakbrook’s renowned steakhouses, indulging in a delicious meal. After dinner, consider catching a live performance at the nearby Drury Lane Theatre. Wind down your first day with a stroll through the well-lit streets, taking in the sights and sounds of the evening.

day 2
Nature and Parks Exploration
morning
:

Start your day with a refreshing walk at the Oak Brook Golf Club, enjoying the scenic views and well-maintained greens. Following your walk, have breakfast at a nearby diner known for its local favorites. The fresh air will rejuvenate you for a day of exploration.

afternoon
:

Spend the afternoon at the Salt Creek Park District, where you can enjoy hiking trails and picnic spots amidst natural beauty. Pack a lunch to savor in the park as you take in the tranquility of the surroundings. If you're feeling adventurous, consider renting a bike to explore more of the trails.

evening
:

As the sun sets, head back to the town for dinner at a farm-to-table restaurant. Savor seasonal dishes made with local ingredients while enjoying the ambiance of dining in Oakbrook. After your meal, take a leisurely evening walk through one of the area’s parks, allowing the peaceful night to envelop you.

day 3
Cultural and Historical Immersion
morning
:

Begin your day with a visit to the Oak Brook Historical Society to learn about the rich history of the area. The museum features engaging exhibits that will deepen your understanding of the community ethos. After your tour, enjoy breakfast at a quaint bakery nearby.

afternoon
:

Dedicate the afternoon to exploring the nearby York Woods County Forest Preserve, where you can engage with nature and enjoy some peaceful time by the river. The picturesque views make it an ideal spot to relax and have a packed lunch. If you're interested, join a guided nature walk to learn more about the local wildlife.

evening
:

Return to Oakbrook for dinner at a popular Italian restaurant known for its homemade pasta. Allow the aromatic dishes to transport your taste buds to Italy as you indulge in local specialties. Conclude your evening with a cozy visit to a local bar for a nightcap, soaking in the warm community vibe.

day 4
Art and Entertainment Day
morning
:

Kick off your day at the Elmhurst Art Museum, where you can explore contemporary art exhibits and installations. After immersing yourself in art, head to a local café for breakfast, sampling house-made pastries. This morning is all about creativity and inspiration.

afternoon
:

After lunch, visit the Mayslake Peabody Mansion and participate in a guided tour of this beautifully restored estate. Learn about its history and enjoy the stunning architecture and grounds. Spend the afternoon in the adjacent forest preserve, where you can take in the beauty of the natural landscape.

evening
:

For dinner, treat yourself to a meal at a trendy gastropub offering a modern twist on American cuisine. Following dinner, make your way to a local cinema or performing arts venue to catch a film or live performance. End the day on a high note, reflecting on the arts as a vibrant part of Oakbrook’s culture.

day 5
Shopping and Leisure
morning
:

Start your day at Oakbrook Center with breakfast at one of its chic cafés, enjoying the upscale shopping environment. After breakfast, map out your strategy for browsing shops and boutiques, taking your time to explore the offerings. This exciting morning sets the tone for retail therapy.

afternoon
:

Continue your shopping spree after enjoying a light lunch at the center. In the afternoon, take a break from shopping to enjoy the beautiful outdoor sculptures and fountains around the complex. This mix of leisure and retail makes for a delightful afternoon.

evening
:

As evening approaches, make reservations for a stylish dinner at a renowned rooftop restaurant with panoramic views. Savor your meal while watching the sunset over Oakbrook, creating a perfect end to a day of shopping. Cap off the night with a sweet treat from a nearby dessert shop to satisfy your cravings.

day 6
Family Fun Day
morning
:

Gather the family for a fun-filled breakfast at a family-friendly diner that offers hearty options for everyone. After fueling up, head to the nearby Brookfield Zoo to explore the incredible exhibits and see a wide variety of animals. The zoo provides an educational experience paired with enjoyable activities for kids.

afternoon
:

Have a picnic lunch at the zoo or venture to a nearby park afterward, where the kids can burn off some energy at the playground. Spend the afternoon engaging in various games and activities. With plenty of open space, it’s a great time for family bonding.

evening
:

Return to Oakbrook for a casual dinner at a restaurant that caters to families, ensuring to order some favorites for everyone. After dinner, enjoy a family movie night at your hotel or visit a local ice cream shop for dessert. Cherish these moments together as you wind down from an exciting day.

day 7
Relaxation and Rejuvenation
morning
:

After a busy week, take this day to relax. Enjoy a leisurely breakfast in your hotel or a nearby café, allowing yourself the luxury of taking it slow. Use this time to recharge and reflect on your trip so far.

afternoon
:

Indulge at a local spa for a treatment or massage that will help you unwind completely. After a soothing experience, take your time sipping tea or coffee at the spa’s relaxation area. The afternoon is all about pampering yourself.

evening
:

To continue your relaxing vibe, dine at a serene restaurant known for its calming atmosphere and smooth jazz music. After dinner, enjoy a peaceful walk along the property or through Oakbrook’s beautiful green spaces. Let the serenity of the evening wrap around you as you savor the tranquil end to your trip.

day 8
Adventure and Sports
morning
:

Get your adrenaline pumping by starting with breakfast at a local café before heading out for a morning of adventure. Check out nearby Oak Brook Golf Club or some indoor activity centers that provide rock climbing or trampoline parks. This lively morning is geared toward active fun.

afternoon
:

After an action-packed morning, indulge in a satisfying lunch at a sports bar, where you can catch some live games while enjoying classic American fare. Post-lunch, consider renting bikes to explore the scenic trails or, on warmer days, enjoy outdoor activities like kayaking at a local lake. Stay active and energized in the afternoon sun.

evening
:

Wind down the day with dinner at a lively sports bar where you can celebrate your day’s activities with fellow enthusiasts. Enjoy the evening atmosphere filled with excitement as you cheer on your favorite teams. Conclude your adventure-filled day with ice cream or dessert at a local spot, reminiscing on the thrilling experiences.

day 9
Farewell to Oakbrook
morning
:

On your last day in Oakbrook, enjoy a relaxing breakfast at your hotel before packing up your belongings. Reflect on your journey and the wonderful experiences you've had during your stay. Capture any final moments with photographs of your favorite spots.

afternoon
:

Before you leave, consider squeezing in a final visit to Oakbrook Center for any last-minute shopping or dining. Take time to grab souvenirs or gifts for loved ones back home. Relish the final hours in this beautiful area, soaking in the atmosphere one last time.

evening
:

As your adventure concludes, head to the airport or train station for your departure. Enjoy a final meal nearby as you prepare for your journey back. Carry the memories of Oakbrook with you and look forward to returning someday.

Discover Oakbrook

Read more in our Oakbrook 2025 Travel Guide.

Oakbrook Travel Guide