Comprehensive 15-Day Midwest and East Coast USA Itinerary: Chicago Graduation, Niagara Falls, and New York City Highlights

Day 1: Arrival and Relax

Chicago, Illinois on May 14, 2025

2:00pm

Check-in at Hotel

Arrive in Chicago and check into your accommodation to relax after your flight. Recommended hotels include Hyatt Regency Chicago, near the Magnificent Mile, for comfort and convenience.
USD150, 2h

4:30pm

Relax and Stroll in Millennium Park

Enjoy a leisurely walk in Millennium Park to see iconic landmarks like Cloud Gate (The Bean). The park closes at 10:00pm, so you have plenty of time to explore.
Free, 1h

6:00pm

Dinner at The Purple Pig

Enjoy Mediterranean-inspired small plates at The Purple Pig, known for its vibrant flavors and great ambiance. Open daily until 10:00pm.
USD40, 1.5h
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Day 2: Explore Chicago

Chicago, Illinois on May 15, 2025

8:00am

Breakfast at Wildberry Pancakes and Cafe

Start your day with delicious pancakes and breakfast specialties at Wildberry Pancakes and Cafe, open from 7:00am.
USD20, 1h

9:30am

Visit Art Institute of Chicago

Spend your morning at the world-class Art Institute of Chicago viewing an extensive collection of art including American Gothic and Impressionist works. Open 10:30am-5:00pm; arrive a bit early to stroll nearby.
USD25, 2h

12:00pm

Lunch at Lou Malnati's Pizzeria

Taste classic Chicago deep-dish pizza at Lou Malnati’s, a local favorite. Open until 10:00pm.
USD25, 1h

2:00pm

Architecture River Cruise

Enjoy an iconic Chicago architecture river cruise that lasts about 90 minutes. Tours usually start between 12:00pm–3:00pm and should be booked in advance.
USD45, 1h30m

4:00pm

Shopping on The Magnificent Mile

Explore the shops and boutiques along Michigan Avenue known as The Magnificent Mile. Stores open until 8:00pm.
Varies, 2h

7:00pm

Dinner at Girl & The Goat

Enjoy innovative dishes at Girl & The Goat, a celebrated Chicago restaurant open until 10:00pm.
USD50, 1.5h
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Day 3: Leisure in Chicago

Chicago, Illinois on May 16, 2025

8:00am

Breakfast at Do-Rite Donuts & Chicken

Taste gourmet donuts and fried chicken; they open at 7:00am.
USD15, 1h

9:30am

Visit Shedd Aquarium

Explore aquatic wildlife from around the world at the Shedd Aquarium. Open 9:00am-5:00pm; purchase tickets in advance.
USD40, 3h

1:00pm

Lunch at The Chicago Diner

Enjoy vegetarian and vegan comfort food classics. Open 11:00am-10:00pm.
USD20, 1h

3:00pm

Afternoon at Field Museum

Discover natural history treasures including Sue the T. rex. Open 9:00am-5:00pm.
USD38, 3h

7:00pm

Dinner at RPM Steak

Savor upscale steakhouse dining in Chicago. Open until 10:00pm.
USD60, 1.5h
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Day 4: Graduation Day

University Park, Illinois on May 17, 2025

7:30am

Breakfast at Hotel or Nearby Cafe

Have an early breakfast to prepare for the day's events. Most cafes open by 7:00am.
USD15, 1h

9:00am

Attend Graduation Ceremony at Governors State University

Celebrate your brother’s graduation ceremony at Governors State University located in University Park, Illinois. Confirm exact ceremony time and location on campus.
Free, 4h

2:00pm

Lunch with Family

Enjoy lunch at a local family-friendly restaurant near University Park such as The Silver Spoke Coffee & Toast.
USD25, 1h

4:00pm

Return to Chicago

Travel back to Chicago and rest at your hotel for the evening.
USD30 (transport), 1h30m

7:00pm

Dinner at Eataly Chicago

Savor Italian cuisine with multiple dining options at Eataly, open until 10:00pm.
USD40, 1.5h
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Day 5: Relax and Visit Navy Pier

Chicago, Illinois on May 18, 2025

8:00am

Breakfast at Yolk

Enjoy a hearty American breakfast at Yolk, open daily at 7:00am.
USD20, 1h

10:00am

Explore Navy Pier

Visit Navy Pier for rides, shops, and waterfront views; it opens daily at 10:00am.
Free entry some rides extra, 3h

1:30pm

Lunch at Harry Caray's Tavern

Enjoy classic American fare in a lively setting at Navy Pier. Open until 10:00pm.
USD30, 1h

3:00pm

Visit Chicago Riverwalk

Stroll along the scenic Chicago Riverwalk, enjoying cafes and public art on the water.
Free, 2h

7:00pm

Dinner at Geja's Cafe

Indulge in a fondue dinner at Geja’s Cafe, romantic and unique, open until 11:00pm.
USD50, 2h
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Day 6: Museum Day and Skydeck

Chicago, Illinois on May 19, 2025

8:00am

Breakfast at Stan's Donuts & Coffee

Start your day with fresh donuts and coffee; open daily 7:00am.
USD15, 1h

9:30am

Visit Museum of Science and Industry

Explore interactive exhibits and the famed U-505 submarine. Open 9:30am-4:00pm.
USD21, 3h

1:00pm

Lunch at the Museum Cafe

Relax and enjoy lunch at the Museum of Science and Industry Cafe, open during museum hours.
USD20, 1h

3:00pm

Visit Willis Tower Skydeck

Experience 360-degree views from the Skydeck of Willis Tower, one of Chicago’s tallest buildings. Open 10:00am-10:00pm.
USD30, 1.5h

6:30pm

Dinner at Joe's Seafood, Prime Steak & Stone Crab

Enjoy classic seafood and steak dishes in a comfortable setting. Open until 10:00pm.
USD60, 1.5h
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Day 7: Packing and Free Time

Chicago, Illinois on May 20, 2025

8:00am

Breakfast at Hotel or Nearby Cafe

Enjoy a relaxed breakfast preparing for your departure to Niagara Falls the next day.
USD15, 1h

10:00am

Free Time for Shopping or Local Exploration

Use the day to visit any missed attractions, revisit your favorite spots or shop local markets.
Varies, 4h

3:00pm

Early Dinner at Lou Malnati's (if missed earlier)

Enjoy a final Chicago deep-dish pizza meal before departure.
USD25, 1h
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Day 8: Travel to Niagara Falls

Niagara Falls, New York on May 21, 2025

8:00am

Travel from Chicago to Niagara Falls (Flight or Drive)

Fly or drive to Niagara Falls, aiming to arrive by afternoon for sightseeing. Flight approx 2-3 hours; driving about 8-9 hours.
USD150-200 (flight), 4-9h

3:00pm

Check-in at Hotel

Hotel options include the Sheraton Niagara Falls, 300 Third Street, +1 716-285-3361, and Wingate by Wyndham Niagara Falls, 555 Buffalo Avenue, +1 716-282-1438, within budget of $200/night.
USD180, 1h

4:00pm

Visit Niagara Falls State Park

Enjoy panoramic views of the falls and take a walk at Niagara Falls State Park. Park is open during daylight hours, check for exact seasonal times.
Free, 2h

7:00pm

Dinner at The Red Coach Inn

Dine with a view near Niagara Falls in this historic restaurant open until 9:00pm.
USD40, 1.5h
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Day 9: Niagara Falls Exploration

Niagara Falls, New York on May 22, 2025

8:00am

Breakfast at Blue Line Diner

Enjoy hearty American breakfast to start your day. Opens at 7:00am.
USD15, 1h

9:30am

Maid of the Mist Boat Tour

Experience an iconic boat tour at the base of the falls. Open daily from April to November, approx 8:30am-6:00pm.
USD25, 1h

11:30am

Visit Cave of the Winds

Walk on decks near the base of the Bridal Veil Falls for an up-close experience. Opens at 9:00am.
USD19, 1.5h

1:30pm

Lunch at Top of the Falls Restaurant

Enjoy lunch with views overlooking Niagara Falls. Open 11:00am-3:00pm.
USD30, 1h

3:00pm

Visit Niagara Gorge Trail

Take leisurely hikes on trails overlooking Niagara Gorge. Open daylight hours.
Free, 2h

7:00pm

Dinner at Casa Mia

Dine on Italian classics near the falls with a cozy ambiance. Open until 10:00pm.
USD35, 1.5h
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Day 10: Travel to New York City

New York City, New York on May 23, 2025

8:00am

Travel from Niagara Falls to NYC

Take a morning flight or bus to New York City. Flights last approx 1.5 hours; buses about 7-8 hours.
USD75-150, 2-8h

2:00pm

Check-in at Hotel NYC

Recommended budget hotels within $200/night include: 1) Pod 39 Hotel, 145 E 39th St, +1 212-545-6500; 2) Fairfield Inn NYC Midtown Manhattan/Penn Station, 325 W 33rd St, +1 212-695-3300; 3) Hotel Edison Times Square, 228 W 47th St, +1 212-245-5000.
USD180, 1h

3:30pm

Visit Times Square

Explore the bustling lights and shops of Times Square, always open and vibrant day and night.
Free, 2h

6:00pm

Dinner at Carmine's Italian Restaurant

Family-style Italian dining in Times Square open until 11:00pm.
USD45, 1.5h
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Day 11: New York City Sightseeing

New York City, New York on May 24, 2025

8:00am

Breakfast at Ess-a-Bagel

Enjoy authentic New York bagels. Open at 6:00am.
USD15, 1h

9:30am

Visit Statue of Liberty and Ellis Island

Take the ferry from Battery Park to visit Liberty Island and Ellis Island. Ferry runs from 8:30am to 4:00pm; expect approx 4-5 hours for the trip.
USD24, 5h

3:30pm

Lunch Near Battery Park

Grab a casual lunch near Battery Park such as at Adrienne's Pizzabar.
USD20, 1h

5:00pm

Visit New York Stock Exchange and Wall Street

See the famous financial district and landmark NYSE building, best viewed from outside during business hours.
Free, 1h

7:00pm

Dinner at Delmonico’s

Historic steakhouse in Financial District open till 10:00pm.
USD55, 1.5h
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Day 12: Explore Midtown NYC

New York City, New York on May 25, 2025

8:00am

Breakfast at Sarabeth's Central Park South

Enjoy upscale breakfast near Central Park. Opens at 8:00am.
USD25, 1h

9:30am

Empire State Building Observatory

Visit the iconic Empire State Building observation deck for city views. Open 8:00am-2:00am.
USD44, 2h

12:00pm

Lunch at The Smith

American bistro with fresh seasonal ingredients. Midtown location open until 10:00pm.
USD30, 1h

1:30pm

Stroll through Central Park

Enjoy the greenery and iconic spots like Bethesda Terrace. Park open all day.
Free, 2h

4:00pm

Visit Museum of Modern Art (MoMA)

View contemporary art masterpieces, open 10:30am-5:30pm.
USD25, 2h

7:00pm

Dinner at Joe’s Shanghai

Famous for soup dumplings, located in Midtown. Open until 10:00pm.
USD40, 1.5h
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Day 13: Final Day NYC

New York City, New York on May 26, 2025

8:00am

Breakfast in Hotel or Nearby Cafe

Relaxed breakfast as you prepare for next day’s trip to New Jersey. Nearby cafes open early.
USD15, 1h

10:00am

Last Minute Shopping or Visit Additional NYC Attractions

Explore any missed landmarks like the High Line or Chelsea Market depending on your interest.
Varies, 3h

2:00pm

Lunch at Magnolia Bakery

Famous for cupcakes and desserts, perfect for a sweet afternoon treat.
USD15, 1h

4:00pm

Relax and Pack

Prepare for next day’s trip to New Jersey.
Free, 2h

7:00pm

Dinner at Local Diner

Casual dinner near your hotel to end your NYC stay.
USD25, 1.5h
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Day 14: Day Trip to Akshardham Temple

New Jersey on May 27, 2025

7:00am

Travel to Akshardham Temple, New Jersey

Depart early by car or public transit for the peaceful Akshardham Temple to explore culturally rich architecture and exhibitions.
USD20 (transport), 2h

9:00am

Visit Akshardham Temple

Explore the stunning temple complex, exhibits, and spiritual environment. Open 9:30am-6:30pm.
Free, 4h

1:00pm

Lunch at Local Indian Restaurant

Enjoy authentic Indian cuisine nearby at a local restaurant open for lunch.
USD25, 1h

2:30pm

Return to New York City

Travel back to NYC to prepare for your departure.
USD20, 2h

6:00pm

Dinner in NYC

Casual dinner at your convenience before flight next day.
USD30, 1.5h
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Day 15: Departure Day

New York City, New York on May 28, 2025

8:00am

Breakfast at Hotel

Have a relaxed breakfast before checking out.
USD15, 1h

10:00am

Prepare and Travel to Airport

Check out of hotel and travel to NYC airport for your flight home. Plan for 2-3 hours prior to departure for check-in and security.
USD40 (transport), 2-3h
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