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Chicago Business and Leisure Trip Itinerary May 29 to June 3, 2025

Viewed by 93 travelers

Day 1: Arrival Day

Chicago, USA on May 29, 2025

5:00pm

Check-In at Hotel

Arrive at the hotel near downtown Chicago, drop off baggage, and freshen up for the evening.
Included in accommodation, 0h30m

6:00pm

Dinner at Lou Malnati's Pizzeria

Enjoy Chicago’s signature deep-dish pizza at this famous local chain. Open daily from 11am to 10pm.
USD25-35, 1h30m

7:45pm

Evening Walk along the Chicago Riverwalk

Experience Chicago’s scenic riverwalk lit up at night with views of iconic architecture and public art.
Free, 1h
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Day 2: Morning Conference, Afternoon Exploration

Chicago, USA on May 30, 2025

7:30am

Breakfast at Wildberry Pancakes and Cafe

Start your day with hearty breakfast pancakes and fresh juices near Millennium Park. Open 7am to 3pm.
USD15-20, 1h

8:00am

Conference Attendance

Attend conference sessions from 8am to 10am at the event venue.
Conference fee, 2h

10:30am

Visit Millennium Park

Explore the iconic Cloud Gate sculpture (The Bean), the Crown Fountain, and serene Lurie Garden. Open 6am to 11pm.
Free, 1h

12:00pm

Lunch at Giordano's

Try Chicago-style deep-dish pizza in a relaxed setting. Open 11am to 10pm.
USD20-30, 1h

1:30pm

Art Institute of Chicago

Visit one of the oldest and largest art museums in the U.S., featuring impressionist and modern masterpieces. Open 10:30am to 5pm.
USD25, 2h

5:30pm

Relax at hotel or networking

Rest or connect with fellow conference attendees.
Free, 1h

7:00pm

Dinner at The Purple Pig

Enjoy Mediterranean small plates in a lively atmosphere. Open 4pm to 10pm.
USD30-40, 1h30m
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Day 3: Morning Conference, Evening Leisure

Chicago, USA on May 31, 2025

7:30am

Breakfast at Yolk

Start with a flavorful breakfast from freshly made omelets and coffee. Open 7am to 3pm.
USD15-20, 1h

8:00am

Conference Attendance

Conference sessions from 8am to 10am.
Conference fee, 2h

10:30am

Walk along the Magnificent Mile

Explore high-end shops, historic buildings, and vibrant street life along Michigan Avenue.
Free, 2h

12:30pm

Lunch at Eataly Chicago

Enjoy Italian market and restaurants offering pasta, pizza, and fresh gelato. Open 10am to 9pm.
USD20-30, 1h

2:00pm

Visit Navy Pier

Experience Chicago's famous lakefront pier with rides, shops, and museums. Open 10am to 10pm.
Free entry; ride prices vary, 2h

5:00pm

Rest and prepare for dinner

Return to the hotel to relax before dinner.
Free, 1h

7:00pm

Dinner at Girl & The Goat

Enjoy creative shared plates from a renowned Chicago chef. Open 5pm to 10pm, reservations recommended.
USD40-60, 2h
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Day 4: Conference and Museum

Chicago, USA on June 1, 2025

7:30am

Breakfast at Do-Rite Donuts & Coffee

Grab fresh donuts with gourmet coffee before the conference. Open 7am to 6pm.
USD10, 30m

8:00am

Morning Conference

Attend the morning conference session.
Conference fee, 2h

10:30am

Field Museum of Natural History

Explore extensive exhibits including Sue the T. rex, ancient artifacts, and cultural displays. Open 9am to 5pm.
USD26, 3h

2:00pm

Lunch at Museum Campus cafes

Casual lunch options available near the museums.
USD15-25, 1h

3:30pm

Relax at hotel or explore nearby

Take rest or enjoy nearby sights at own pace.
Free, 1h

6:30pm

Dinner at The Signature Room at the 95th

Dine with panoramic views atop the John Hancock Center, open 4pm to 10pm.
USD50-70, 2h
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Day 5: Final Conference, Night Out

Chicago, USA on June 2, 2025

7:30am

Breakfast at the hotel or nearby café

Enjoy a convenient breakfast to fuel final conference day.
USD15, 1h

8:00am

Attend last conference session

Wrap up the conference activities with morning session.
Conference fee, 2h

10:30am

Visit Shedd Aquarium

Explore aquatic exhibits featuring marine life from around the world. Open 9am to 5pm.
USD39, 2h

12:30pm

Lunch at The Chicago Firehouse Restaurant

Enjoy hearty American cuisine in a historic firehouse setting. Open 11am to 10pm.
USD25, 1h

2:00pm

Free afternoon for shopping or relaxation

Use your free time to revisit favorite spots or relax before evening.
Varies, 3h

7:00pm

Dinner and Jazz at The Green Mill

Experience Chicago’s historic jazz club, featuring live music and classic cocktails. Open 5pm to 2am.
USD30-50, 2h
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Day 6: Departure Day

Chicago, USA on June 3, 2025

6:00am

Early Breakfast at Hotel

Grab a quick breakfast before checkout.
Included or USD15, 30m

7:00am

Check-out and Transfer to Airport

Depart hotel and head to airport for early flight.
Varies, 1h
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Plan Your Chicago may 29 at 5pm to June 3 at 8am,, attending a conference Trip

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