Chicago Usa 2 Day Itinerary

48 Hours in the Windy City: A 2-Day Itinerary

This itinerary assumes you’re arriving in Chicago with 2 full days to explore. Feel free to adjust it based on your interests and time constraints!

Day 1: Iconic Chicago & Museum Hopping

  • Morning:

    • Arrival: Arrive at O’Hare International Airport (ORD) or Midway International Airport (MDW).

    • Transportation:

      • From ORD: Take the CTA Blue Line train to downtown Chicago. It’s a direct and affordable option, but be aware it can take 45 minutes to an hour depending on your destination. From there, you can easily explore on foot, by public transportation, or utilize Chicago’s bike-sharing program.
      • From MDW: This airport is closer to downtown if you choose to stay near the city, and you can connect directly to the “L” train system via the CTA Orange Line.

    • Morning (9:00 am - 12:00 pm): Start your day with a taste of Chicago history at the Chicago History Museum. Explore exhibits on the Great Chicago Fire, the city’s industrial past, and its cultural evolution.

    • Lunch (12:00 pm - 1:30 pm): Grab a classic Chicago hot dog for lunch. Remember, no ketchup!

    • Recommended Spots:

      • Portillo’s Hot Dogs: A popular chain known for its delicious Chicago-style hot dogs and Italian beef sandwiches.
      • Gene & Jude’s Hot Dogs: A local favorite with a focus on the classic Chicago hot dog.

  • Afternoon:

    • Art: Immerse yourself in art at the Art Institute of Chicago, one of the world’s leading art museums, home to iconic masterpieces like Grant Wood’s “American Gothic” and Edward Hopper’s “Nighthawks”.
    • Architecture: Take a boat tour on the Chicago River. You’ll see stunning views of the city’s skyline and learn about its architectural history and marvels from a unique perspective.

  • Things to Know:

    • The Chicago Architecture Foundation River Cruise is a must-do for architecture enthusiasts, but any cruise along the Chicago River will offer breathtaking cityscape glimpses.

    • Many restaurants and cafes in Chicago accept reservations online or by phone.

    • Lunch (12:00 pm - 1:30 pm): Enjoy deep-dish pizza at Lou Malnati’s Pizzeria or Giordano’s for a truly Chicago experience.

      • Lou Malnati’s Pizzeria is known for its buttery, flaky crust.
      • Giordano’s offers a variety of toppings and often has long lines due to its popularity.

  • Evening (7:00 pm - 10:00 pm:

    • Dinner:

      • Fine Dining: Experience the culinary creativity of Chicago with a meal at a renowned restaurant like Alinea or Next.

      • Things to Know:

        • Be prepared for a high price tag and make reservations well in advance, as these restaurants are highly acclaimed and sought after.

        • Dinner (7:00 pm - 10:00 pm):

          • For a Taste of Chicago’s history:

            • Chicago History Foundation River Cruise: Enjoy a delicious deep-dish pizza at Pequod’s Pizza, known for its caramelized crust and cheese that goes all the way to the edge.

          • For a taste of Chicago’s classics:

            • Deep-Dish Pizza: Grab a slice (or two!) of this iconic dish from a local pizzeria.
            • Garrett Popcorn Shops: Enjoy a classic Chicago “cheese & caramel” popcorn mix for a sweet and savory treat.

  • Alternative Evening Options:

    • Nightlife: Explore the vibrant nightlife scene in neighborhoods like Wicker Park, Logan Square, or River North.
    • Entertainment: Catch a show at the iconic Chicago Theatre, known for its elaborate architecture and marquee.

Day 2: Exploring the City

  • Morning (9:00 am - 12:00 pm):

    • Architecture Exploration: Visit the Skydeck Chicago at Willis Tower (formerly Sears Tower) for stunning views and a unique “leaning” experience.

    • Things to do in Chicago:

      • Explore the city’s museums: Enjoy a picnic lunch in Millennium Park, home to the famous Cloud Gate sculpture (“The Bean”)

      • Catch a game: Cheer on the Cubs at Wrigley Field or the White Sox at Guaranteed Rate Field.

        • For a unique dining experience:
          • Wrigleyville: Head to the Chicago Cubs’ rooftop bar, where you can enjoy the game and some drinks.

  • Lunch (12:00 pm - 2:00 pm: Enjoy lunch at one of Chicago’s many restaurants, exploring local flavors like Garrett Popcorn’s famous “Chicago Mix” (cheese & caramel popcorn) or a delicious Italian Beef Sandwich. * Food Recommendation: Alinea for a high-end culinary experience.

  • Dinner:

    • Deep Dish Pizza: Try the “deep-dish” pizza at Pequod’s Pizza, a local favorite known for its crispy, caramelized crust and deep-dish pizza.
      • For a unique dining experience:
        • Chicago Style Pizza: Enjoy classic Italian beef sandwiches with gravy and giardiniera.

Things to Know:

  • Dining at the “Chicago Mix”

  • Public Transportation: Consider using public transportation for getting around. The CTA (Chicago Transit Authority) offers a variety of options, including buses, trains, and the “L” system.

    • Museum Exploration:
      • Take a stroll through the vibrant Navy Pier. It’s a great place to enjoy the sights and sounds of the city while walking along the waterfront.

Other things to do:

  • Explore the Magnificent Mile: This iconic stretch of Michigan Avenue is known for its upscale shopping, fine dining, and entertainment options.
  • Take a walk through Millennium Park: This urban oasis offers stunning architecture, public art like the “Cloud Gate” sculpture (aka “The Bean”), and plenty of green space to enjoy.

For a unique experience:

  • Visit the Museum of Science and Industry for a different perspective on Chicago’s history.
  • Explore the Field Museum, which houses an impressive collection of dinosaur fossils and artifacts from around the world.

Things to consider:

  • Chicago-style hot dogs are a culinary tradition and you need to learn the rules:

    • No ketchup: This is a cardinal sin in Chicago hot dog culture.
    • “Chicago Mix”: Try this unique combination of sweet and savory flavors by ordering a “deep dish” with cheese and marinating it in gravy (and giardiniera).
    • Budget: Be aware that deep-dish pizza can be expensive, but the experience is worth it!

Enjoy a scenic walk or bike ride along the Chicago Riverwalk:

  • Wrigleyville: Enjoy the vibrant atmosphere and stunning views of the city from the “L” train.

  • Consider using the “Chicago Mix” for a unique culinary experience.

This is just a suggestion, but it’s important to remember that this is a starting point. You can adapt it to your own interests and budget. For example:

  • For a unique and delicious twist: Try the classic Chicago-style hot dog (no ketchup!) or a “Chicago-style” pizza at Pizzeria Uno for a taste of the local culinary scene.

  • Explore other “Chicago Classics”: Enjoy a game of softball or just a stroll on the beach, and soak in the city’s diverse offerings.