Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Romantic Honeymoon in Chicago: 5-Day Itinerary

Viewed by 95 travelers

Day 1: Arrival and Exploration

Chicago, USA

9:00AM

Breakfast at Wildberry Pancakes and Cafe

Kick off your honeymoon with a delightful breakfast of fluffy pancakes and fresh strawberry compote at this beloved local eatery.
Located near Millennium Park, a short walk to your next destination.
USD25, 1 hour

10:30AM

Visit Millennium Park

Stroll through the iconic park, taking in the famous Cloud Gate sculpture and enjoying the lush gardens.
Walking distance from Wildberry Pancakes.
Free, 2 hours

12:30PM

Lunch at The Gage

Treat yourselves to a romantic lunch with a view at this upscale pub-style restaurant known for its hearty dishes.
Just a 10-minute walk from Millennium Park.
USD60, 1.5 hours

2:00PM

Chicago River Architecture Cruise

Discover the stunning architecture of Chicago from the water on a scenic boat cruise.
Head towards the Chicago Riverwalk, 10 minutes' walk from The Gage.
USD40, 1.5 hours

4:00PM

Check-in at The Langham Chicago

Relax at this luxurious riverside hotel with stunning skyline views, a perfect spot for honeymooners.
Your hotel is just a short 10-minute walk from the Riverwalk.
Varies, 1 hour

7:00PM

Dinner at Girl & The Goat

Indulge in a unique dining experience at this acclaimed restaurant known for innovative global dishes.
A short 5-minute taxi or rideshare from your hotel.
USD120, 2 hours
Find Hotels in Chicago

Day 2: Art and Culture Day

Chicago, USA

8:30AM

Breakfast at Beatrix

Enjoy a healthy breakfast with an array of options, particularly their famous avocado toast.
Short 5-minute taxi ride from hotel.
USD30, 1 hour

10:00AM

Visit Art Institute of Chicago

Wander through the impressive collection of artworks including Grant Wood's American Gothic.
Just a 10-minute walk from Beatrix.
USD25, 2.5 hours

12:30PM

Lunch at Lou Malnati's Pizzeria

Experience Chicago’s famous deep-dish pizza for lunch at this iconic spot.
10 minutes' walk from the Art Institute.
USD50, 1 hour

2:00PM

Stroll at Grant Park

Take a leisurely walk through beautiful Grant Park, enjoying the lush scenery together.
A short 5-minute walk from Lou Malnati's.
Free, 1.5 hours

4:00PM

Visit the Field Museum

Explore one of the largest natural history museums in the world, featuring fascinating exhibits.
15-minute taxi ride from Grant Park.
USD34, 2 hours

7:00PM

Dinner at The Signature Room

Enjoy a romantic dinner with incredible skyline views on the 95th floor of the John Hancock Center.
A 15-minute taxi ride from the Field Museum.
USD150, 2 hours
Find Hotels in Chicago

Day 3: Adventure and Fun

Chicago, USA

9:00AM

Breakfast at Egg Harbor Cafe

Start your day with a hearty breakfast equipped with scrumptious original recipes.
A 15-minute taxi from The Langham.
USD35, 1 hour

10:30AM

Visit Shedd Aquarium

Explore the mesmerizing marine life at this renowned aquarium, great for couples.
A short 10-minute taxi from Egg Harbor Cafe.
USD40, 2 hours

1:00PM

Lunch at the Little Goat Diner

Grab a delicious and whimsically crafted lunch in a cozy diner-style atmosphere.
A 5-minute taxi from the aquarium.
USD50, 1 hour

2:30PM

Visit Adler Planetarium

Immerse yourselves in the wonders of the universe at the oldest planetarium in the Western Hemisphere.
A 10-minute walk from the Little Goat.
USD19, 2 hours

5:00PM

Relax at Navy Pier

Enjoy the scenic waterfront, take a ride on the Ferris wheel, and soak in the beautiful views.
A 15-minute taxi ride from Adler Planetarium.
USD25 (Ferris Wheel), 2 hours

7:00PM

Dinner at RPM Steak

Savor a memorable dinner featuring prime steaks and quality wines in a chic setting.
A short 10-minute taxi ride from Navy Pier.
USD180, 2 hours
Find Hotels in Chicago

Day 4: Romantic Evening

Chicago, USA

9:00AM

Breakfast at Toast

Savor a delicious breakfast made from fresh locally-sourced ingredients.
Just a 12-minute taxi ride from your hotel.
USD30, 1 hour

10:30AM

Visit Lincoln Park Zoo

Enjoy a free day at this lovely zoo where you can leisurely watch animals in a peaceful setting.
A short 10-minute taxi ride from Toast.
Free, 2 hours

1:00PM

Lunch at Café Ba-Ba-Reeba!

Relish tapas-style dining with Spanish influences in a vibrant setting.
A 15-minute walk from the zoo.
USD60, 1.5 hours

3:00PM

Visit John Hancock Observatory

Experience sweeping views of the city from this observation deck for a romantic encounter.
15-minute taxi from the Café.
USD25, 1 hour

5:00PM

Couples' Spa Time at The Langham

Indulge in a stress-relieving couples’ spa treatment, perfectly designed for a romantic afternoon.
Return to your hotel, just a 10-minute taxi.
Varies, 2 hours

7:30PM

Private Dinner Cruise

Enjoy a romantic dinner cruising along the Chicago River, admiring the city skyline from the water.
Pick-up provided from the hotel.
USD300, 3 hours
Find Hotels in Chicago

Day 5: Farewell and Memories

Chicago, USA

9:00AM

Breakfast at Corner Bakery Cafe

Enjoy a light breakfast with freshly brewed coffee and delightful pastries to start your day.
A short 10-minute walk from your hotel.
USD15, 1 hour

10:30AM

Visit The Magic Parlour

Experience an extraordinary magic show that provides a delightful and memorable finale to your honeymoon.
15-minute taxi ride from the cafe.
USD75, 2 hours

1:00PM

Lunch at The Purple Pig

Indulge in a delicious Mediterranean-inspired lunch, perfect for a memorable last meal in Chicago.
A 10-minute taxi from The Magic Parlour.
USD70, 1.5 hours

3:00PM

Shopping on Michigan Avenue

Browse high-end boutiques and gift shops on the famous Magnificent Mile for your travel souvenirs.
Just a short walk from the restaurant.
Varies, 2 hours

6:00PM

Dinner at Sable Kitchen & Bar

Conclude your romantic getaway with a final dinner that features delicious locally-sourced dishes and cocktails.
A 10-minute taxi back to your hotel.
USD110, 2 hours
Find Hotels in Chicago
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version

More About Chicago

Trip Packing List: Chicago (Late February 2026)
Packing List
Trip Packing List: Ahmedabad → Abu Dhabi → Chicago (4 Jun–11 Jul)
Packing List
Chicago Weather Guide: Mid-May Transitions & Lake Breezes
Weather Guide
Chicago Weather & Climate Guide: Seasons in the Windy City
Weather Guide
Full Guide to Michelin Star Cities: 2025 Updated List
Travel Expert
Global Michelin Cities & US Travel Tiers from New York
Travel Expert
Itinerary created by AI-assisted, human-reviewed

Plan Your Chicago Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go