How many days do you need in Chicago?

This itinerary covers 7 days in Chicago, which is a great amount of time to explore the main highlights. Depending on your pace and interests, you could extend or shorten the trip.

What is the best itinerary for Chicago?

Plan your perfect 7 days trip to Chicago. This detailed travel itinerary includes daily activities, local recommendations, and insider tips to make your journey unforgettable.

Discovering Chicago in 7 Days

Day 1: City Centre Delights

Chicago, USA

8:00AM

Breakfast at Do-Rite Donuts & Chicken

Start your day with a delicious combination of freshly made donuts and crispy chicken at this popular spot in the city centre.

GBP 10, 1 hour

10:00AM

Visit Millennium Park

Explore the famous Cloud Gate sculpture, also known as 'The Bean', and enjoy the beautiful landscapes of Millennium Park.

Free, 2 hours

1:00PM

Lunch at Lou Malnati's Pizzeria

Indulge in Chicago's renowned deep-dish pizza at this authentic pizzeria.

GBP 20, 1.5 hours

3:00PM

Art Institute of Chicago

Immerse yourself in a world-class art collection, including works by Picasso and Van Gogh, at the Art Institute of Chicago.

GBP 15, 2 hours

6:00PM

Dinner at Girl & the Goat

Experience innovative flavours and dishes crafted by award-winning chef Stephanie Izard at this trendy restaurant.

GBP 30, 2 hours

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Day 2: Neighbourhood Charm

Chicago, USA

9:00AM

Breakfast at Bang Bang Pie & Biscuits

Start your day with delicious homemade pies and fluffy biscuits at this cosy neighbourhood spot.

GBP 12, 1 hour

11:00AM

Explore Wicker Park

Discover the hip and artistic vibe of Wicker Park with its boutique shops, street art, and quirky cafes.

Free, 2 hours

1:30PM

Lunch at Big Star

Savour delicious tacos and margaritas at this popular taqueria in Wicker Park.

GBP 18, 1.5 hours

3:30PM

Visit 606 Trail

Walk or bike along the elevated 606 Trail, a former rail line turned urban park offering great views of the city.

Free, 1.5 hours

6:00PM

Dinner at Parachute

Experience Korean-American fusion cuisine in a relaxed setting at the Michelin-starred restaurant Parachute.

GBP 35, 2 hours

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Day 3: Cultural Immersion

Chicago, USA

8:00AM

Breakfast at The Bongo Room

Enjoy creative and indulgent brunch options at The Bongo Room, known for its delicious pancakes and seasonal dishes.

GBP 15, 1 hour

10:00AM

Visit Museum Campus

Explore the Field Museum, Shedd Aquarium, and Adler Planetarium all conveniently located together at Museum Campus.

GBP 40 (for all 3 museums), 3 hours

1:00PM

Lunch at Ricobene's

Try the classic breaded steak sandwich at Ricobene's, a local favourite near the Museum Campus area.

GBP 10, 1 hour

3:00PM

Visit Chinatown

Discover the vibrant culture and cuisine of Chicago's Chinatown with its bustling shops and delicious eateries.

Free, 2 hours

6:00PM

Dinner at Duck Duck Goat

Indulge in mouth-watering Chinese food with a creative twist at Duck Duck Goat, a top-rated restaurant in Chinatown.

GBP 25, 2 hours

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Day 4: Lakefront Serenity

Chicago, USA

9:00AM

Breakfast at Original Pancake House

Start your day with fluffy pancakes and hearty breakfast options at this beloved breakfast spot.

GBP 10, 1 hour

11:00AM

Bike along Lakefront Trail

Rent a bike and enjoy a scenic ride along the picturesque Lake Michigan on the Lakefront Trail.

GBP 15 (bike rental), 2 hours

1:30PM

Lunch at The Signature Room

Dine with stunning views of the city skyline at The Signature Room on the 95th floor of the John Hancock Center.

GBP 30, 1.5 hours

3:30PM

Navy Pier Exploration

Visit Navy Pier for a mix of attractions, including the Centennial Wheel, Pier Park, and lakefront views.

GBP 20 (for attractions), 2 hours

6:30PM

Dinner at GT Fish & Oyster

Savour fresh seafood and oysters prepared with a modern twist at GT Fish & Oyster, a renowned restaurant near Navy Pier.

GBP 40, 2 hours

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Day 5: Historic Chicago

Chicago, USA

8:00AM

Breakfast at Yolk

Fuel up with hearty breakfast options and delicious pancakes at Yolk, a popular breakfast spot in River North.

GBP 15, 1 hour

10:00AM

Explore The Loop

Stroll through The Loop district to admire the iconic architecture, including the Willis Tower and the Chicago Cultural Center.

Free, 2 hours

1:00PM

Lunch at Al's Beef

Taste the famous Italian beef sandwich at Al's Beef, a local institution in The Loop.

GBP 10, 1 hour

3:00PM

Visit Chicago History Museum

Step back in time and explore the rich history of Chicago at the Chicago History Museum, showcasing artefacts and exhibits.

GBP 12, 2 hours

6:00PM

Dinner at The Purple Pig

Indulge in a variety of Mediterranean-inspired small plates and wine selections at the lively restaurant, The Purple Pig.

GBP 35, 2 hours

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Day 6: Green Spaces & Museums

Chicago, USA

9:00AM

Breakfast at Beatrix

Start your day with healthy and wholesome breakfast options at Beatrix, known for its fresh juices and morning favourites.

GBP 20, 1 hour

11:00AM

Art & Nature at Lincoln Park

Explore the Lincoln Park Zoo, Lincoln Park Conservatory, and stroll through the scenic gardens and green spaces of Lincoln Park.

Free, 3 hours

2:00PM

Lunch at Café Ba-Ba-Reeba!

Enjoy a Spanish tapas feast at Café Ba-Ba-Reeba!, offering a variety of small plates and sangrias.

GBP 25, 1.5 hours

4:00PM

Visit The Peggy Notebaert Nature Museum

Discover the natural world through interactive exhibits and displays at The Peggy Notebaert Nature Museum in Lincoln Park.

GBP 10, 1.5 hours

6:30PM

Dinner at The J. Parker

Enjoy panoramic views of the city skyline while dining on the rooftop of The J. Parker, offering a sophisticated atmosphere and crafted cocktails.

GBP 40, 2 hours

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Day 7: Culinary & Cultural Farewell

Chicago, USA

8:00AM

Breakfast at Wildberry Pancakes and Cafe

Indulge in a variety of pancake creations and breakfast favourites at Wildberry Pancakes and Cafe to kick off your final day in Chicago.

GBP 18, 1 hour

10:00AM

Chicago Riverwalk

Take a leisurely stroll along the Chicago Riverwalk, lined with cafes, public art installations, and beautiful views of the city's architecture.

Free, 2 hours

1:00PM

Lunch at Revival Food Hall

Experience a gastronomic paradise at Revival Food Hall, a vibrant food market showcasing diverse culinary offerings from local chefs and vendors.

GBP 20, 1.5 hours

3:00PM

Chicago Cultural Experience

Immerse yourself in the arts and culture of Chicago by visiting the Chicago Cultural Center, with its stunning Tiffany glass dome and rotating exhibitions.

Free, 2 hours

6:00PM

Farewell Dinner at Alinea

Conclude your Chicago adventure with an unforgettable dining experience at Alinea, a three-Michelin-star restaurant renowned for its innovative and artistic approach to cuisine.

GBP 250, 3 hours

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Step 1 Outline Preview:

Discovering Chicago in 7 Days

Day 1: City Centre Delights

8:00AM

10:00AM

1:00PM

3:00PM

6:00PM

Day 2: Neighbourhood Charm

9:00AM

11:00AM

1:30PM

3:30PM

6:00PM

Day 3: Cultural Immersion

8:00AM

10:00AM

1:00PM

3:00PM

6:00PM

Day 4: Lakefront Serenity

9:00AM

11:00AM

1:30PM

3:30PM

6:30PM

Day 5: Historic Chicago

8:00AM

10:00AM

1:00PM

3:00PM

6:00PM

Day 6: Green Spaces & Museums

9:00AM

11:00AM

2:00PM

4:00PM

6:30PM

Day 7: Culinary & Cultural Farewell

8:00AM

10:00AM

1:00PM

3:00PM

6:00PM

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