Affordable 5-Day Honeymoon Itinerary in Chicago

Day 1: Explore Downtown

Chicago, USA

8:00AM

Breakfast at Wildberry Pancakes and Cafe

Start your honeymoon with a delicious stack of pancakes at this popular spot, known for its inventive breakfast menu.
Located just a short walk from Millennium Park.
USD20, 1 hour

9:30AM

Visit Millennium Park

Stroll through the iconic park and take your picture with the famous Cloud Gate sculpture, also known as 'The Bean'.
Just a 5-minute walk from the cafe.
Free, 1.5 hours

11:00AM

Explore Art Institute of Chicago

Wander through world-class art collections, and don’t miss the Impressionist paintings.
A 10-minute walk from Millennium Park.
USD25 (free admission on Tuesday from 5PM to 8PM), 2 hours

1:00PM

Lunch at Giordano's

Experience Chicago’s famous deep-dish pizza at this famed eatery.
A 15-minute walk from the Art Institute.
USD30, 1.5 hours

3:00PM

Walk along the Riverwalk

Take a leisurely stroll along the scenic riverwalk and enjoy the view of the skyline.
Riverwalk is right next to Giordano's.
Free, 1 hour

4:30PM

Visit Chicago Cultural Center

Discover beautiful architecture and free art exhibits, a perfect quiet retreat in the city.
A quick 10-minute walk from the Riverwalk.
Free, 1 hour

6:00PM

Dinner at The Purple Pig

End your day with Mediterranean-inspired dishes and perhaps a glass of wine to toast your first day.
A scenic 15-minute walk back towards the Magnificent Mile.
USD50, 2 hours
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Day 2: Navy Pier Adventures

Chicago, USA

8:00AM

Breakfast at Lou Mitchell's

Enjoy a hearty breakfast at this Chicago institution known for its warm atmosphere and classic diner food.
Take the 'L' blue line from State/Lake to Clark/Lake, then walk 15 minutes.
USD25, 1 hour

9:30AM

Explore Navy Pier

Wander along the iconic pier filled with shops, entertainment, and stunning views of Lake Michigan.
Walk from the cafe to Navy Pier.
Free (some attractions may cost), 2 hours

12:00PM

Lunch at Chicago Bagel Authority

Grab a delicious bagel sandwich at this casual eatery, perfect for a quick and budget-friendly meal.
A 15-minute bus ride from Navy Pier.
USD15, 1 hour

1:30PM

Ride the Centennial Wheel

Experience breathtaking views of the skyline and lake from above.
Back at Navy Pier, easy walk to the wheel.
USD18 per person, 1 hour

3:00PM

Visit the Chicago Children's Museum

Even if you don’t have kids, this museum is filled with fun interactive exhibits.
Located on Navy Pier.
USD19, 2 hours

5:00PM

Dinner at Portillo’s

Taste classic Chicago-style hot dogs and Italian beef sandwiches at this local favorite.
Take the bus towards downtown.
USD25, 1.5 hours

7:00PM

Catch a Free Concert at Millennium Park

Enjoy a romantic evening under the stars, with various genres of music available during the summer.
Return to Millennium Park directly from Portillo’s.
Free, 2 hours
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Day 3: Lincoln Park & Lakefront Fun

Chicago, USA

8:00AM

Breakfast at The Brown Bag

Start your day off right with a fresh and fulfilling breakfast sandwich and coffee.
Located near Lincoln Park, accessible via the 'L' train.
USD20, 1 hour

9:00AM

Visit Lincoln Park Zoo

Explore this free zoo that houses a variety of animals and beautiful gardens.
Walk from the cafe to the zoo.
Free, 1.5 hours

10:30AM

Relax in Lincoln Park

Take a peaceful stroll or enjoy a bit of quiet time in the surrounding park.
The park is adjacent to the zoo.
Free, 1 hour

12:00PM

Lunch at Cafe Brauer

Savor local cuisine with a view of the lake at this delightful cafe housed in a historic building.
Walk back to the zoo entrance.
USD25, 1 hour

1:30PM

Wander Along the Lakefront Trail

Enjoy a lovely walk along Lake Michigan, taking in the skyline views, and fresh air.
Access the trail from the park.
Free, 2 hours

3:30PM

Visit the Chicago History Museum

Discover the history of Chicago through engaging exhibits that capture the city's evolution.
A short bus or 'L' ride from the lakefront.
USD19, 1.5 hours

5:00PM

Dinner at The Cheesecake Factory

Pick from a wide range of options on the extensive menu and don’t forget to try a slice of cheesecake!
Take public transport back to downtown.
USD40, 2 hours

7:30PM

Enjoy a Night Walk at Navy Pier

Take in the lights of the pier and enjoy a romantic evening atmosphere.
A bus can take you back to the pier.
Free, 1 hour
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Day 4: Art and Culture Day

Chicago, USA

8:00AM

Breakfast at Intelligentsia Coffee

Enjoy artisanal coffee and fresh pastries to fuel your day of exploration.
Located in the Loop, close to cultural sites.
USD15, 1 hour

9:00AM

Visit the Museum of Contemporary Art

Immerse yourself in the diverse and impressive contemporary art collection.
A short walk from the cafe.
USD15, 1.5 hours

10:30AM

Explore the Water Tower Place

Spend time shopping or window shopping in this iconic shopping mall known for its architecture.
A 10-minute walk from the museum.
Free (shopping varies), 1 hour

12:00PM

Lunch at Chicago Q

Indulge in some Chicago-style barbecue at this authentic restaurant.
A 15-minute walk from Water Tower Place.
USD30, 1.5 hours

1:30PM

Visit the Lincoln Park Conservatory

Wander through stunning floral displays and exotic plants in this beautiful conservatory.
Take the bus or a short ride on the 'L'.
Free, 1.5 hours

3:00PM

Relax in the Park

Take some time to unwind and enjoy the surroundings of Lincoln Park.
A walk away from the Conservatory.
Free, 1 hour

4:00PM

Explore the Chicago Riverwalk

Enjoy the scenic beauty of the river and take a few memorable photos.
Easily accessible from Lincoln Park.
Free, 1 hour

6:00PM

Dinner at Navy Pier

Finish your day at one of the many affordable dining options available at this waterfront attraction.
Head back to Navy Pier.
USD40, 1.5 hours
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Day 5: Relax and Unwind

Chicago, USA

8:00AM

Breakfast at Yolk

Delight in a flavorful breakfast at this vibrant eatery celebrating breakfast favorites.
Located in River North, accessible via the 'L'.
USD20, 1 hour

9:00AM

Visit the Field Museum

Explore the fascinating exhibits of natural history and culture at one of the largest museums in the country.
Take public transport to Museum Campus.
USD32, 2 hours

11:00AM

Discover Shedd Aquarium

Immerse yourselves in the underwater world and enjoy spectacular marine life.
A short walk from the Field Museum.
USD39, 2 hours

1:00PM

Lunch at Lou Malnati's Pizzeria

Indulge in another deep-dish pizza experience at this local favorite before heading home.
A bus ride back towards downtown.
USD30, 1.5 hours

2:30PM

Relax at Grant Park

Take a leisurely walk or rest on the grass, reflecting on your wonderful honeymoon.
A short walk from Lou Malnati's.
Free, 1 hour

3:30PM

Visit Macy's on State Street

Browse through this iconic department store and perhaps pick up a souvenir.
A short walk from Grant Park.
Free (shopping varies), 1.5 hours

5:00PM

Dinner at a Local Food Truck

End your honeymoon trip with affordable and delicious street food, such as tacos or gourmet sandwiches.
Many food trucks are located around downtown; just take a look!
USD20, 1 hour

6:30PM

Enjoy Sunset at the Lakefront

Wrap up your trip by witnessing a picturesque sunset over Lake Michigan.
A short walk from wherever you are downtown.
Free, 1 hour
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