Comprehensive Multi-City USA and Canada Travel Itinerary from Nairobi

Day 1: Travel Day

Nairobi to Chicago, Kenya to USA on July 9, 2025

10:00pm

Flight from Nairobi to Chicago

Depart from Jomo Kenyatta International Airport on Turkish Airlines heading to O'Hare International Airport in Chicago.
USD0, Approx 15h
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Day 2: Rest Day

Chicago, USA on July 10, 2025

8:00am

Breakfast at Wildberry Pancakes and Cafe

Enjoy classic American breakfast with pancakes and fresh coffee to recover from jet lag. Open from 7:00am to 3:00pm.
USD15, 1h

10:00am

Relax and Rest at Hotel

Take the day to rest and recover from travel at your Chicago hotel.
USD0, Rest of day

6:00pm

Dinner at Lou Malnati's Pizzeria

Taste Chicago deep-dish pizza at this famous restaurant open from 11:00am to 10:00pm.
USD25, 1.5h
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Day 3: Explore Chicago

Chicago, USA on July 11, 2025

8:00am

Breakfast at Yolk

Enjoy a variety of breakfast options with local fresh ingredients. Open 7:00am to 3:00pm.
USD15, 1h

9:30am

Visit Millennium Park

Explore this iconic park known for Cloud Gate and interactive art spaces. Open 6:00am to 11:00pm.
Free, 1h30m

11:30am

Explore Art Institute of Chicago

Visit one of America’s top art museums featuring classics and modern art. Open 10:30am to 5:00pm; closed Tuesdays.
USD25, 2h

2:00pm

Lunch at Giordano's

Indulge in authentic Chicago stuffed deep-dish pizza. Open 11:00am to 10:00pm.
USD20, 1h

3:30pm

Architectural River Cruise

Take an iconic 90-minute guided boat tour showcasing Chicago’s world-famous architecture. Runs from 10:00am until 7:00pm in summer.
USD45, 1h30m

6:00pm

Dinner at The Purple Pig

Enjoy Mediterranean small plates and wine, open until 10:00pm.
USD40, 1.5h
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Day 4: Fly to Orlando

Chicago to Orlando, USA on July 12, 2025

7:00am

Breakfast at Do-Rite Donuts & Chicken

Quick and delicious breakfast before your flight. Open 7:00am to 12:00pm.
USD10, 30m

9:00am

Flight to Orlando

Depart from Midway Airport on Southwest Airlines to Orlando International Airport.
USD100, 3h

1:00pm

Lunch at Se7en Bites

Enjoy comfort Southern meals and pastries in Orlando, open 10:00am to 3:00pm.
USD15, 1h

3:00pm

Rest and Prepare for Conference

Check into hotel and relax before Lions Conference events begin.
USD0, Rest of day

7:00pm

Dinner Nearby Hotel

Choose a nearby steakhouse or American cuisine for a soothing dinner before two conference days. Many restaurants open until 10:00pm.
USD30, 1.5h
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Day 5: Lions Conference

Orlando, USA on July 13, 2025

7:30am

Breakfast at Hotel

Start your day with a quick breakfast included in your hotel stay or at a nearby café.
USD0-20, 1h

9:00am

Attend Lions Conference

Participate in conference sessions and networking throughout the day.
USD0 (conference ticket), All day

12:00pm

Lunch at Conference Venue

Enjoy catered lunch during the conference breaks.
USD0-30, 1h

6:00pm

Dinner with Conference Group

Join a group dinner arranged by the conference or explore local dining options like The Boathouse at Disney Springs, open until 10:00pm.
USD40, 2h
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Day 6: Lions Conference

Orlando, USA on July 14, 2025

7:30am

Breakfast at Hotel

Enjoy a hearty breakfast to prepare for a full conference day.
USD0-20, 1h

9:00am

Attend Lions Conference

Engage in sessions and networking opportunities throughout the day.
USD0, All day

12:00pm

Lunch at Conference Venue

Convenient meal break at conference location.
USD0-30, 1h

7:00pm

Dinner at Prato

Enjoy modern Italian cuisine within walking distance of many hotels, open until 10:00pm.
USD40, 1.5h
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Day 7: Travel Day

Orlando to Richmond, USA on July 15, 2025

8:00am

Breakfast at Keke's Breakfast Cafe

Fuel up with well-known Florida breakfast classics open 7:00am to 2:00pm.
USD15, 1h

10:00am

Flight to Richmond

Fly from Orlando International Airport to Richmond International Airport on Southwest Airlines.
USD150, 2h

12:30pm

Lunch at Millie West

Experience modern American cuisine with an emphasis on local ingredients. Open 11:30am to 3:00pm on weekdays.
USD25, 1h

2:00pm

Check into Yagnesh Mama's Place

Relax in the comfortable accommodation and get ready for Richmond activities.
USD0, Rest of day

7:00pm

Dinner at Mama J’s Kitchen

Try traditional Southern soul food at this cozy Richmond spot open until 9:00pm.
USD20, 1.5h
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Day 8: Stay at Yagnesh Mama's Place

Richmond, USA on July 16, 2025

8:00am

Breakfast at Yagnesh Mama's Place

Enjoy homemade breakfast prepared by Yagnesh Mama, offering a local and personal touch.
Included, 1h

10:00am

Visit Virginia Museum of Fine Arts

Explore an extensive collection of art ranging from ancient to contemporary. Open 10:00am to 5:00pm.
USD0, 2h

1:00pm

Lunch at Perly’s

Savor Jewish deli classics with a modern twist, open until 3:00pm on weekdays.
USD20, 1h

3:00pm

Explore Historic Church Hill

Walk and admire one of Richmond’s oldest neighborhoods. Free and open all day.
Free, 2h

7:00pm

Dinner at L’opossum

Enjoy eclectic American-French cuisine at this top Richmond restaurant, open until 9:00pm.
USD45, 1.5h
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Day 9: Stay at Yagnesh Mama's Place

Richmond, USA on July 17, 2025

8:00am

Breakfast at Yagnesh Mama's Place

Start your day with a delicious homemade breakfast.
Included, 1h

10:00am

Visit Maymont Park and Mansion

Tour beautiful gardens, mansion, and wildlife exhibits. Open 10:00am to 6:00pm.
USD14, 3h

1:30pm

Lunch at Edo’s Squid

A local favorite for Italian seafood and pasta, open till 9:00pm.
USD25, 1h

3:00pm

Relax and enjoy afternoon at Yagnesh Mama's Place

Unwind and prepare for the next day’s plans.
USD0, Afternoon

7:00pm

Dinner at The Roosevelt

Fine southern-inspired dining in historic Church Hill, open till 10:00pm.
USD40, 1.5h
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Day 10: Stay at Yagnesh Mama's Place

Richmond, USA on July 18, 2025

8:00am

Breakfast at Yagnesh Mama's Place

Enjoy another great homemade breakfast to start your day.
Included, 1h

10:00am

Tour American Civil War Museum

Learn about Richmond’s pivotal Civil War history with engaging exhibits. Open 10:00am to 5:00pm.
USD15, 2h

12:30pm

Lunch at Kuba Kuba

Enjoy Cuban-inspired street food flavors in a modern vibrant atmosphere, open till 10:00pm.
USD20, 1h

2:00pm

Walk the Canal Walk

Stroll along Richmond’s scenic canal featuring museums and shops. Free and open all day.
Free, 2h

7:00pm

Dinner at Heritage

Dine in a Southern fine dining establishment open till 10:00pm.
USD45, 1.5h
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Day 11: Departure Prep

Richmond, USA on July 19, 2025

8:00am

Breakfast at Yagnesh Mama's Place

Enjoy your final homemade breakfast before travel preparations.
Included, 1h

10:00am

Free Time or Local Shopping

Use the morning to shop for souvenirs or take a final walk around Richmond.
Varies, 2h

12:30pm

Lunch at Hot Chick

Casual spot for Nashville-style hot chicken, open until 8:00pm.
USD15, 1h

Afternoon

Pack and Relax at Accommodation

Prepare for your flight back to Chicago the next day.
USD0, Rest of day

7:00pm

Dinner at Yagnesh Mama's Place

Enjoy a comforting home-cooked meal for your final night in Richmond.
Included, 1.5h
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Day 12: Travel Day

Richmond to Chicago, USA on July 20, 2025

7:00am

Breakfast at Yagnesh Mama's Place

Early homemade breakfast before departure.
Included, 1h

9:30am

Flight to Chicago

Depart Richmond International Airport on Southwest Airlines to Chicago Midway Airport.
USD100, 2h

12:00pm

Check into Chicago Hotel and Lunch

Settle in and have lunch at Portillo’s for classic Chicago-style hot dogs and Italian beef sandwiches, open till 10pm.
USD15, 1h

2:00pm

Rest or Light Sightseeing

Relax or stroll nearby Millennium Park and Riverwalk.
Free, Afternoon

7:00pm

Dinner at The Signature Room at the 95th

Dine with panoramic views of Chicago skyline. Open daily till 10:00pm.
USD60, 2h
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Day 13: Explore Chicago

Chicago, USA on July 21, 2025

8:00am

Breakfast at Ann Sather

Famous for Swedish cinnamon rolls and hearty breakfasts. Open 8am-3pm.
USD15, 1h

9:30am

Shedd Aquarium Visit

Explore aquatic life at this renowned public aquarium. Open 9:00am to 5:00pm.
USD40, 2h

12:00pm

Lunch at The Field Bistro

Located within Shedd Aquarium, enjoy fresh cuisine open 11:30am-3pm.
USD25, 1h

1:30pm

Visit Field Museum

Discover natural history exhibits including Sue the T. rex. Open 9am-5pm.
USD30, 3h

5:00pm

Rest at hotel

Relax after a busy day.
USD0, Evening

7:30pm

Dinner at Girl & The Goat

Trendy restaurant with shared plates; reservations recommended. Open till 10pm.
USD50, 1.5h
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Day 14: Explore Chicago

Chicago, USA on July 22, 2025

8:00am

Breakfast at Bongo Room

Known for creative pancakes and hearty breakfasts. Open 8am-2pm.
USD15, 1h

9:30am

Visit Museum of Science and Industry

Largest science museum in the Western Hemisphere featuring interactive exhibits. Open 9:30am-4:00pm.
USD22, 3h

1:00pm

Lunch at The Publican

Rustic-chic eatery famous for pork dishes and seafood, open noon to 10pm.
USD30, 1h

2:30pm

Walk along The 606 Trail

Elevated urban trail for walking and biking with city views. Open sunrise to sunset, free entry.
Free, 2h

7:00pm

Dinner at RPM Italian

Popular upscale Italian restaurant with modern ambiance, open till 10:00pm.
USD60, 1.5h
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Day 15: Explore Chicago

Chicago, USA on July 23, 2025

8:00am

Breakfast at The Bop Bar

Enjoy unique breakfast dishes in a casual urban setting, open 7am to 2pm.
USD15, 1h

10:00am

Skydeck Chicago at Willis Tower

Experience breathtaking city views from the iconic glass ledge. Open 9:00am to 10:00pm.
USD30, 1h

11:30am

Shopping on the Magnificent Mile

Explore boutiques and flagship stores on Chicago’s famous shopping street.
Varies, 2h

2:00pm

Lunch at Eataly Chicago

Italian marketplace with various restaurants and cafes, open till 10pm.
USD25, 1h

3:30pm

Visit Chicago Riverwalk

Scenic pedestrian waterfront area with cafes and public art. Free and open all day.
Free, 2h

7:00pm

Dinner at Alinea

World-renowned 3-Michelin-star restaurant with avant-garde cuisine, reservations required. Open till 10pm.
USD250, 3h
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Day 16: Fly to Vancouver

Chicago to Vancouver, USA to Canada on July 24, 2025

7:00am

Breakfast at Hotel

Enjoy a quick breakfast to prepare for your flight.
USD0-20, 1h

9:00am

Flight to Vancouver

Catch your flight from Chicago to Vancouver International Airport.
USD200, Approx 4h30m

1:30pm

Lunch at Vij's

Famous Indian restaurant in Vancouver known for creative dishes, open 5pm to 10:30pm but lunch reservations recommended in some locations.
USD40, 1.5h

3:30pm

Check into Vancouver Hotel and Relax

Settle in and rest from travel.
USD0, Evening

7:00pm

Dinner at Miku Vancouver

Renowned sushi restaurant with waterfront views. Open till 10:00pm.
USD50, 1.5h
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Day 17: Explore Vancouver

Vancouver, Canada on July 25, 2025

8:00am

Breakfast at Jam Cafe

Popular spot serving hearty comfort breakfast all day. Open 8am to 3pm.
CAD15, 1h

9:30am

Stanley Park Visit

Explore one of the world's best urban parks with trails and seawall views. Open 24 hours, free entrance.
Free, 3h

1:00pm

Lunch at The Teahouse in Stanley Park

Sit down for a scenic meal inside the park. Open 11am-8pm.
CAD30, 1h

2:30pm

Visit Vancouver Aquarium

Within Stanley Park, enjoy marine animal exhibits. Open 10am-5pm.
CAD38, 2h

6:30pm

Dinner at Blue Water Cafe

Award-winning seafood restaurant in Yaletown, open till 10pm.
CAD60, 1.5h
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Day 18: Explore Vancouver

Vancouver, Canada on July 26, 2025

8:00am

Breakfast at Café Artigiano

Craft coffee and pastries to start your day. Open 7am-5pm.
CAD10, 45m

9:00am

Capilano Suspension Bridge Park

Explore rainforest trails and iconic suspension bridges. Open 9:00am to 7:00pm.
CAD56, 3h

12:30pm

Lunch at nearby Capilano River Cafe

Casual dining close to the park, open till 8:00pm.
CAD25, 1h

2:00pm

Visit Granville Island Public Market

Local artisan foods and shops in a vibrant market atmosphere. Open 9am-7pm.
Free, 2h

7:00pm

Dinner at The Sandbar Seafood Restaurant

Seafood dining on Granville Island open until 10pm.
CAD50, 1.5h
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Day 19: Explore Vancouver

Vancouver, Canada on July 27, 2025

8:30am

Breakfast at Purebread

Indulge in delicious baked goods and coffee. Open 7:00am to 6:00pm.
CAD10, 45m

9:30am

Visit Grouse Mountain

Scenic mountain with hiking, zip line, and wildlife refuge. Skyride open 8:45am-9:45pm.
CAD61 (for Skyride and attractions), 4h

2:00pm

Lunch at Altitudes Bistro on Grouse Mountain

Enjoy dining with mountain views, open till 3pm.
CAD35, 1h

4:00pm

Return to Vancouver Downtown

Relax at your hotel or explore local shops.
Free, Evening

7:00pm

Dinner at Hawksworth Restaurant

Upscale Canadian cuisine in the heart of Vancouver. Reservations recommended. Open till 10pm.
CAD70, 2h
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Day 20: Explore Vancouver

Vancouver, Canada on July 28, 2025

8:00am

Breakfast at Medina Café

Famous for brunch and waffles, open 8am to 3pm.
CAD20, 1h

9:30am

Visit Museum of Anthropology

Explore indigenous art and culture at UBC campus. Opens at 10:00am to 5:00pm.
CAD18, 2h

12:00pm

Lunch at nearby Mahony & Sons Pub

Casual dining with great views. Open all day.
CAD25, 1h

1:30pm

Walk Kitsilano Beach

Popular urban beach area for relaxation and scenic views. Open all day, free.
Free, 2h

7:00pm

Dinner at Cioppino's Mediterranean Grill

Warm Mediterranean flavors with cozy ambiance. Open till 10pm.
CAD50, 1.5h
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Day 21: Explore Vancouver

Vancouver, Canada on July 29, 2025

8:00am

Breakfast at Thierry

French bakery and cafe, open from 7:30am to 6:00pm.
CAD15, 1h

9:30am

Explore Gastown

Historic district with cobblestone streets, shops, and the steam clock. Perfect for a morning stroll.
Free, 2h

12:00pm

Lunch at Water Street Café

Comfort food with locally sourced ingredients in Gastown, open till 3pm.
CAD25, 1h

1:30pm

Visit Vancouver Art Gallery

Features contemporary and classic art exhibits. Open 10am-5pm.
CAD24, 2h

7:00pm

Dinner at Nightingale

Modern Canadian bistro with craft cocktails. Open till 10pm.
CAD55, 1.5h
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Day 22: Explore Vancouver

Vancouver, Canada on July 30, 2025

8:00am

Breakfast at Café Medina

Known for Belgian waffles and Mediterranean inspired dishes. Open 8am-3pm.
CAD20, 1h

9:30am

Bike or Walk Seawall

Enjoy Vancouver’s waterfront scenic seawall circuit. Rentals available near Stanley Park.
CAD15, 3h

1:00pm

Lunch at The Fish Shack

Casual spot for fresh seafood and chowder, open till 9pm.
CAD25, 1h

2:30pm

Visit Science World

Interactive scientific exhibits and Omnimax theater. Open 10am-5pm.
CAD29, 2h

7:00pm

Dinner at Burdock & Co

Farm-to-table dining with seasonal menus. Open till 9:30pm.
CAD55, 1.5h
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Day 23: Last Vancouver Day

Vancouver, Canada on July 31, 2025

8:00am

Breakfast at Greenhorn Café

Known for hearty breakfasts and friendly ambiance. Open 7am-3pm.
CAD15, 1h

9:30am

Visit Queen Elizabeth Park

Beautiful gardens and panoramic city views. Open 7am-10pm, free.
Free, 2h

12:00pm

Lunch at Seasons in the Park

Upscale dining with spectacular views within Queen Elizabeth Park. Open till 2:30pm.
CAD35, 1h

2:30pm

Free Afternoon for Last-minute Souvenirs

Explore shops or rest before journey home.
Varies, Afternoon

7:00pm

Farewell Dinner at Market by Jean-Georges

Elegant seasonal local cuisine, open till 10pm.
CAD70, 2h
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Day 24: Travel to Chicago

Vancouver to Chicago, Canada to USA on August 1, 2025

8:00am

Breakfast at Hotel

Enjoy a quick breakfast before your departure flight.
CAD0-20, 1h

10:00am

Flight to Chicago

Fly from Vancouver to Chicago to complete your itinerary loop.
USD200, Approx 4h

2:30pm

Check into Chicago Hotel and Rest

Relax after your flight in your Chicago hotel.
USD0, Afternoon

7:00pm

Dinner at Ema

Mediterranean-inspired small plates in a trendy setting, open until 10pm.
USD50, 1.5h
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Day 25: Explore Chicago

Chicago, USA on August 2, 2025

8:00am

Breakfast at The Original Pancake House

Classic pancake dishes and more, open 7am-3pm.
USD15, 1h

9:30am

Visit Navy Pier

Enjoy waterfront attractions including The Centennial Wheel. Open 10am-8pm.
Free entry; ride costs extra, 3h

1:00pm

Lunch at Big Bowl

Asian fusion dishes near Navy Pier, open till 10pm.
USD25, 1h

2:30pm

Free afternoon or shopping on State Street

Explore popular shopping district or relax.
Varies, Afternoon

7:00pm

Dinner at Gibsons Bar & Steakhouse

Classic Chicago steakhouse experience open till 10pm.
USD60, 1.5h
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Day 26: Relax and Prepare

Chicago, USA on August 3, 2025

8:00am

Breakfast at Hotel

Enjoy the morning at leisure before travel activities or flights.
USD0-20, 1h

Daytime

Optional sightseeing or last-minute shopping

Use the day for flexible rest or exploration per your preference.
Varies, All day

Evening

Light dinner at hotel or nearby eatery

Prepare for your international flights beginning next day.
USD20, 1h
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Day 27: Flight to Istanbul

Chicago to Istanbul, USA to Turkey on August 6, 2025

10:00am

Flight from Chicago to Istanbul

Depart Chicago O'Hare on Turkish Airlines for Istanbul flight.
USD800, Approx 10h
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Day 28: Flight to Nairobi

Istanbul to Nairobi, Turkey to Kenya on August 7, 2025

2:00pm

Flight from Istanbul to Nairobi

Complete your return journey with Turkish Airlines to Nairobi Jomo Kenyatta Intl Airport.
USD400, Approx 6h
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Day 29: Arrive Nairobi

Nairobi, Kenya on August 8, 2025

9:00am

Arrive in Nairobi

Welcome home after your extensive multi-city North American and Canadian trip.
USD0, N/A
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