5-Day Chicago Adventure: From Madison to the Windy City

Day 1: Travel to Chicago

Madison, WI on March 4, 2025

10:00AM

Depart Madison

Leave Madison, WI to set out for a fulfilling trip to Chicago, just a 2.5-hour drive south through beautiful Wisconsin landscapes.
CURRENCY0, 2.5 hours

12:30PM

Lunch at Lou Malnati's

Upon arrival, enjoy a classic Chicago deep-dish pizza from Lou Malnati's, famed for its buttery crust and rich flavors.
CURRENCY20, 1 hour

1:30PM

Millennium Park

Stroll through Millennium Park and see Cloud Gate, better known as 'The Bean', and take in the stunning architecture and public art.
CURRENCY0, 2 hours

4:00PM

Check-in at Hotel

Settle into your hotel conveniently located downtown, ready to explore the sights.
CURRENCY150, Soaking in atmosphere

6:00PM

Dinner at Giordano's

Experience another style of Chicago pizza with the renowned stuffed deep-dish pizza at Giordano's, a beloved local chain.
CURRENCY25, 1.5 hours

8:00PM

Chicago Riverwalk

Take an evening stroll along the Chicago Riverwalk, enjoying the city lights and ambiance as the day ends.
CURRENCY0, 1 hour
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Day 2: Art & History

Chicago, IL on March 5, 2025

8:00AM

Breakfast at The Bongo Room

Start your day with a decadent breakfast at The Bongo Room, famous for its creative pancakes and locally-sourced ingredients.
CURRENCY15, 1 hour

9:30AM

Art Institute of Chicago

Visit the Art Institute of Chicago, home to a vast collection of masterpieces, including works by Monet and Van Gogh.
CURRENCY25, 3 hours

12:30PM

Lunch at Portillo's

Indulge in Chicago-style hot dogs and Italian beef sandwiches at Portillo's, a must-try for a true Chicago lunch.
CURRENCY15, 1 hour

1:30PM

Field Museum

Explore the wonders of the natural history at the Field Museum, featuring famous exhibits like Sue the T. rex.
CURRENCY30, 3 hours

5:00PM

Dinner at The Capital Grille

Enjoy a fine dining experience with dry-aged steaks and a vast wine selection at The Capital Grille.
CURRENCY60, 2 hours

7:30PM

Night out at Second City

Catch an improv show at The Second City, known for its hilarious performances and iconic comedians.
CURRENCY40, 2 hours
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Day 3: Architecture & Views

Chicago, IL on March 6, 2025

8:00AM

Breakfast at Wildberry Pancakes & Cafe

Start your day with fluffy pancakes and delicious omelets at Wildberry, a favorite of locals before heading out to sightsee.
CURRENCY15, 1 hour

9:30AM

Chicago Architecture Boat Tour

Experience a unique perspective of Chicago’s architectural skyline with a guided boat tour on the Chicago River.
CURRENCY40, 1.5 hours

11:30AM

Visit Willis Tower Skydeck

Get breathtaking views from the Willis Tower Skydeck, where you can step onto 'The Ledge' - a glass balcony extending over the city.
CURRENCY40, 2 hours

1:30PM

Lunch at Shake Shack

Grab a quick bite at Shake Shack, enjoying their famous ShackBurgers and crinkle-cut fries.
CURRENCY15, 1 hour

2:30PM

Explore Navy Pier

Spend your afternoon wandering Navy Pier, with attractions, shops, and fantastic views of Lake Michigan.
CURRENCY0, 3 hours

6:00PM

Dinner at RPM Italian

Savor fresh pasta and delicious Italian fare at RPM Italian, a stylish restaurant with a fantastic menu.
CURRENCY45, 2 hours

8:30PM

Chicago Symphony Orchestra

If you're a music lover, enjoy an evening performance by the renowned Chicago Symphony Orchestra.
CURRENCY60, 2 hours
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Day 4: Neighborhoods & Culture

Chicago, IL on March 7, 2025

8:00AM

Breakfast at Beatrix

Relish in a delightful breakfast at Beatrix, known for its healthy options and homemade pastries.
CURRENCY15, 1 hour

9:30AM

Visit Lincoln Park Zoo

Visit Lincoln Park Zoo, a free admission zoo home to over 1,000 animals in a beautiful urban park setting.
CURRENCY0, 2 hours

12:00PM

Lunch at Wishbone

Enjoy a delicious Southern comfort meal at Wishbone, with their famous chicken and waffles.
CURRENCY20, 1 hour

1:00PM

Explore Wicker Park

Wander through the vibrant Wicker Park neighborhood, filled with boutiques, cafes, and street art.
CURRENCY0, 2 hours

3:00PM

Visit Chicago History Museum

Dive into the rich history of Chicago at the Chicago History Museum, featuring interactive exhibits and fascinating stories.
CURRENCY20, 1.5 hours

5:00PM

Dinner at Al's Beef

Try the well-known Italian Beef sandwich at Al's Beef, a local staple that people rave about.
CURRENCY10, 1.5 hours

7:00PM

Evening Stroll on the Lakefront Trail

Take a leisurely evening walk along the Lakefront Trail, enjoying scenic views of Lake Michigan and city skyline.
CURRENCY0, 1 Hour
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Day 5: Return to Madison

Chicago, IL on March 8, 2025

8:00AM

Breakfast at Blue Door Kitchen & Garden

Enjoy a cozy breakfast at Blue Door Kitchen, with farm-to-table dishes that satisfy your morning cravings.
CURRENCY20, 1 hour

9:30AM

Last-minute Shopping in Magnificent Mile

Explore the shops along Magnificent Mile for last-minute gifts and souvenirs before leaving Chicago.
CURRENCY0, 2 hours

11:30AM

Lunch at The Cheesecake Factory

Grab an early lunch at The Cheesecake Factory, renowned for a diverse menu and delicious desserts.
CURRENCY20, 1 hour

1:00PM

Depart for Madison

Head back to Madison, reminiscing about the wonderful memories made during your trip.
CURRENCY0, 2.5 hours
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