Chicago, Illinois 5-Day Trip Itinerary

Travel to Chicago

Drive from Lyons, WI to downtown Chicago.

Expect some traffic as you get closer to the city center.

Hotel Check-in

Check into your hotel, drop off luggage, and get settled for your Chicago adventure.

Lunch on Magnificent Mile

Enjoy a casual lunch at one of the many restaurants or cafes along the iconic Magnificent Mile, offering diverse cuisines.

Millennium Park & The Bean

Explore Millennium Park, home to the famous 'Cloud Gate' sculpture (The Bean), Crown Fountain, and Lurie Garden.

Perfect for photos!

Free to visit. Best time for photos is earlier in the morning or later afternoon to avoid crowds.

Art Institute of Chicago (Exterior & Gift Shop)

Admire the stunning architecture of the Art Institute from the outside and browse its extensive gift shop. If time allows, consider a quick visit to a specific gallery.

Full admission can take hours. Consider focusing on a specific wing if you're short on time. Booking tickets in advance is recommended if you plan to enter. Admission for a full visit is around USD 32 per person.

Deep-Dish Pizza Dinner

Indulge in Chicago's culinary icon: deep-dish pizza!

Choose from famous spots like Lou Malnati's, Giordano's, or Gino's East.

Expect a wait during peak dinner hours. Deep dish takes longer to cook than regular pizza.

Rooftop Drinks with a View

Enjoy evening cocktails and stunning city views at a rooftop bar in downtown Chicago, such as Cindy's Rooftop or LondonHouse Chicago.

Dress code may apply. Reservations recommended for larger groups.

Breakfast Downtown

Grab breakfast at a local cafe or diner near your hotel before a day of exploration.

Chicago Architecture Boat Tour

Take a highly-rated boat tour on the Chicago River to learn about the city's famous architecture and history from a unique perspective.

Book tickets in advance, especially for mid-morning tours. It's a popular activity. Dress in layers as it can be breezy on the river.

Lunch in River North

Enjoy lunch in the River North neighborhood, known for its diverse restaurants and vibrant atmosphere.

The Field Museum

Immerse yourselves in natural history at The Field Museum, home to Sue the T-Rex, ancient Egyptian artifacts, and fascinating exhibits on cultures and evolution.

Can easily spend half a day here. Purchase tickets online in advance to save time and potentially money.

Dinner in West Loop

Experience Chicago's renowned foodie district with dinner in the West Loop, offering a vast array of high-quality restaurants from casual to fine dining.

Reservations are highly recommended for popular restaurants in this area.

Jazz or Blues Club

Enjoy Chicago's legendary jazz and blues scene at a live music venue like Buddy Guy's Legends or Kingston Mines.

Check schedules for live performances. Cover charges typically apply.

Breakfast at Local Eatery

Seek out a highly-rated local breakfast spot, perhaps a classic Chicago diner or a trendy brunch cafe.

Navy Pier & Centennial Wheel

Visit Navy Pier, enjoy the lakeside atmosphere, and ride the iconic Centennial Wheel for panoramic views of the city skyline and Lake Michigan.

Plenty of shops, restaurants, and attractions at Navy Pier. You could also rent bikes here for a ride along the lakefront.

Lunch at Navy Pier

Have lunch at one of the many casual dining options available at Navy Pier, ranging from fast food to sit-down restaurants.

Magnificent Mile Shopping

Spend the afternoon browsing the upscale shops, department stores, and boutiques along Michigan Avenue, known as the Magnificent Mile.

Great for window shopping or finding unique souvenirs. Water Tower Place is a popular vertical mall.

Stroll through Lincoln Park

Take a relaxing walk through a portion of Lincoln Park, enjoying the green space, views of the skyline, and perhaps a glimpse of the free Lincoln Park Zoo.

The Lincoln Park Zoo is free and open daily, offering a pleasant walk-through if you have extra time.

Dinner in Old Town

Dine in the historic Old Town neighborhood, famous for its Victorian buildings and diverse selection of restaurants.

Consider trying a restaurant with outdoor seating if the weather is nice.

Second City Comedy Show

Catch a hilarious improv or sketch comedy show at The Second City, where many famous comedians got their start.

Book tickets well in advance, especially for weekend shows. Shows are typically 90 minutes with an intermission.

Breakfast at Hotel

Enjoy breakfast at your hotel or a nearby cafe.

Museum of Science & Industry

Spend the morning at the incredible Museum of Science and Industry, featuring a German U-boat, a coal mine, and hands-on exhibits.

This museum is quite large and requires travel to the Hyde Park neighborhood. Allow ample time. Book tickets online.

Chicago Gangster & Crime Tour (Alternative)

Alternatively, delve into Chicago's notorious past on a walking tour focused on Prohibition-era gangsters, mobsters, and famous crime sites.

Requires walking. Check tour specific meeting points. An adult-oriented tour.

Lunch Near Museum or Loop

Have lunch in Hyde Park if you visited MSI, or head back to The Loop for a quick bite if you took the gangster tour.

Skydeck Chicago (Willis Tower)

Dare to step onto The Ledge at Skydeck Chicago for breathtaking panoramic views of the city from the Willis Tower (formerly Sears Tower).

Book timed-entry tickets online in advance to avoid long waits, especially on weekends. Photography highly encouraged.

Farewell Dinner

Enjoy a special farewell dinner at a highly-rated Chicago restaurant.

Consider a steakhouse or a restaurant with a unique culinary focus.

Reservations are essential for popular fine dining spots.

Evening Stroll along Riverwalk

Take a leisurely evening stroll along the Chicago Riverwalk, enjoying the illuminated skyline and vibrant atmosphere.

Many bars and restaurants line the Riverwalk for a final drink if desired.

Leisurely Brunch

Enjoy a relaxing brunch at a popular Chicago spot, a perfect way to cap off your foodie adventures.

Brunch spots can be very popular on Sundays; arrive early or expect a wait. Some places take reservations.

Last-Minute Souvenirs

Grab any last-minute souvenirs or gifts from shops near your brunch spot or hotel.

Many shops on Michigan Avenue or State Street offer souvenirs.

Hotel Check-out

Complete check-out procedures at your hotel.

Depart Chicago for Home

Begin your drive back to Lyons, WI, concluding your memorable friends' getaway to Chicago.