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Chicago Bears Game Weekend Itinerary: A Tailgate Experience and Adventures in the Windy City

Viewed by 113 travelers

Day 1: Arrival and City Exploration

Chicago, Illinois

9:00AM

Breakfast at Wildberry Pancakes and Cafe

Kick off your weekend with a hearty breakfast at Wildberry Pancakes, famous for their mouth-watering pancakes and fresh berry toppings.
Take a 5-minute Uber ride from your hotel.
USD 30, 1 hour

10:30AM

Explore Millennium Park

Stroll through Millennium Park, where you can admire the Cloud Gate sculpture and enjoy the vibrant atmosphere.
A 10-minute walk from Wildberry.
Free, 1.5 hours

12:00PM

Lunch at The Purple Pig

Savor a delicious Mediterranean-style lunch at The Purple Pig, known for its tapas and charcuterie boards.
A 15-minute walk from Millennium Park.
USD 60, 1.5 hours

1:30PM

Visit the Art Institute of Chicago

Explore the Art Institute's incredible collections, from classic to contemporary, ensuring a culturally enriching afternoon.
A 10-minute walk from The Purple Pig.
USD 25, 2.5 hours

4:00PM

Check into Hotel and Relax

Return to your hotel to freshen up and unwind before the evening's activities.
A 10-minute taxi ride back.
USD 0, 1 hour

6:00PM

Dinner at Girl & The Goat

Indulge in a delightful dinner at Girl & The Goat, where seasonal ingredients shine in an innovative menu.
A quick 10-minute ride to the restaurant.
USD 100, 2 hours

8:30PM

Evening Nightcap at The Aviary

Wind down with a cocktail at The Aviary, a trendy spot known for its creative drink presentations.
An easy 10-minute walk from the restaurant.
USD 50, 1.5 hours
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Day 2: Game Day Experience

Chicago, Illinois

8:30AM

Breakfast at Lou Mitchell's

Start your game day at Lou Mitchell's, a beloved diner serving up classic breakfasts and complimentary donuts.
An 8-minute walk from your hotel.
USD 25, 1 hour

10:00AM

Explore Soldier Field

Head to Soldier Field early to explore the stadium and immerse yourself in the game day atmosphere amongst fellow Bears fans.
A 15-minute taxi ride to the iconic stadium.
USD 0, 1 hour

11:00AM

Tailgate Party at Soldier Field

Join the pre-game festivities with a vibrant tailgate party where you can enjoy food, drinks, and connect with fellow fans.
Participate in the tailgate right outside Soldier Field.
USD 40 (assuming food and drinks), 1 hour

12:00PM

Chicago Bears vs. Opponent Game

Cheer on the Chicago Bears as they take on their opponents in Soldier Field, sharing an unforgettable game day experience together.
Head inside the stadium as the gates open before kickoff.
USD 200 (average ticket price), 3.5 hours

3:30PM

Post-Game Celebration

Celebrate the game (win or lose) at a nearby sports bar, reflecting on the excitement of the day while enjoying spirited company.
Walk to a nearby bar within 5-10 minutes.
USD 50, 2 hours

5:30PM

Dinner at Portillo's

Indulge in classic Chicago-style comfort food, including deep-dish pizza and Italian beef at Portillo's.
A 10-minute taxi ride from the sports bar.
USD 30, 1.5 hours

7:00PM

Evening Stroll along the Riverwalk

Conclude your day with a romantic evening stroll along the Chicago Riverwalk, enjoying the illuminated skyline.
A 10-minute ride to the Riverwalk.
Free, 1 hour
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Day 3: Relax and Unwind

Chicago, Illinois

9:00AM

Breakfast in Bed

Relax and enjoy breakfast in bed, featuring pancakes, fresh fruit, and coffee.
Room Service.
USD 40, 1 hour

10:30AM

Visit Chicago Botanic Garden

Take a peaceful excursion to the Chicago Botanic Garden, absorbing quiet beauty and fragrant blooms.
A taxi ride of about 30 minutes.
Free, 2 hours

1:00PM

Lunch at Café Zuppa

Stop for a light and cozy lunch at Café Zuppa, featuring homemade soups and hearty sandwiches.
Drive back to the city, about 30 minutes.
USD 35, 1 hour

2:30PM

Explore Lincoln Park Zoo

Enjoy a leisurely visit to Lincoln Park Zoo, a free zoo where you can observe animals and relax in a natural setting.
A quick 10-minute drive from the café.
Free, 2 hours

5:00PM

Shopping on Magnificent Mile

Spend the afternoon shopping along the Magnificent Mile, exploring the variety of luxury boutiques and shops.
15-minute drive to Magnificent Mile.
Varies, 2.5 hours

8:00PM

Last Dinner at Alinea

Conclude your romantic getaway with a spectacular dining experience at Alinea, acclaimed for its innovative dining concepts.
A 10-minute ride from Magnificent Mile.
USD 400, 3 hours

11:00PM

Wrap Up with a Nightcap

Finish your trip with a nightcap at The Signature Lounge in the John Hancock Center for breathtaking views of the city.
A quick 10-minute ride.
USD 50, 1 hour
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