48 hours in Chicago: The perfect two-day itinerary

Famous for its architecture, pizzas, sports, and jazz music, Chicago — on the shore of Lake Michigan — is one of the biggest and boldest cities in the US. Ready to find out what makes Chicago the “Mecca of the Midwest”? This two-day itinerary maps it all out for you.

  1. Day 1

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    1. Morning

      See the largest T-Rex ever discovered at the Field Museum (2 hours)

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      The Field Museum of Natural History offers the chance to get up close and personal with your favorite dinosaurs, including the star of the show, Sue — the largest and most complete Tyrannosaurus Rex skeleton ever discovered. The museum is set up for self-guided exploration, but if you book a VIP Tour a few days in advance, you’ll get inside the museum before it even opens to the crowds. If your interests are more Finding Nemo than Jurassic Park, then kick off your Chicago adventure at Shedd Aquarium next door. Check out over 32,000 marine animals living in 5 million gallons of water, making it one of the largest aquariums in the world.
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    2. Walk Chicago’s “front yard” to find its famous deep-dish pizza (1.5 hours)

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      Make your way through Grant Park and spend some time in the exact location where Michael Jordan and the Chicago Bulls celebrated each of their six NBA championships. Use Lakefront Trail, a pedestrian-only pathway popular with runners and cyclists, to pass the picturesque Buckingham Fountain and cross the Chicago Marathon finish line, without much effort, on Columbus Drive. When you reach the park’s north side, seek out Giordano’s or Pizano’s for the best of Chicago’s famous deep-dish pizza. An authentic deep-dish takes about 45 minutes to prepare, so do as the Chicagoans do and call ahead to place your order so it’s ready by the time you arrive.

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    3. Afternoon

      Strike a pose at Cloud Gate (30 minutes)

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      Ease yourself out of your food coma with a short walk to Cloud Gate in Millennium Park. Better known as The Bean, this massive sculpture by Sir Anish Kapoor is the first of his permanent public outdoor works in the United States. Designed to reflect the impressive Chicago skyline, Cloud Gate has become one of the city’s most-visited locations. Check there’s no pizza sauce left on your face before snapping the quintessential Chicago selfie.

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    4. See the city’s architecture from the Chicago River (1.5 hours)

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      Chicago is a city known for architectural achievements, not least the birthplace of the skyscraper. The best vantage point to see it all? From the water. Book a spot on this architecture tour and find yourself in the heart of downtown, making your way along all three branches of the Chicago River as your tour guide tells the story of the city from the ground up. You’ll need a bit more time for the Lake and River Cruise option as you’ll also go through the Chicago Locks to enter the vast Lake Michigan, but it’s worth it for the best views. In winter, when the water is probably ice, brave the hop-on hop-off tour’s top deck for an up-close look.

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    5. Evening

      End the day with a bang at Navy Pier (2 hours)

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      Spend your first Chicago evening on the shores of Lake Michigan at Navy Pier, filled to the brim with rides, games, live music, and dining. Walk all the way to the eastern edge of the pier and look back at the city to spot some of your favorites from the architecture tour as their colors change at sundown. Want to watch a Chicago sunset? Head to the top of Centennial Wheel for the best skyline views, and skip the line with a Fastpass ticket. As day turns into night, sit back and enjoy the nightly fireworks show with popcorn from Garrett Popcorn Shop, which has been popping since 1949.
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    6. See the city light up at the Art on the Mart show (1.5 hours)

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      The Art on the Mart light show is a free 30-minute show that projects mesmerizing displays onto the side of the Merchandise Mart building along the Chicago Riverwalk. Grab a viewing spot by The Jetty, between Wells Street and Franklin Street. Shows begin at 9:00 PM and 9:30 PM in summer, or 7:30 PM and 8:00 PM the rest of the year, so you have two chances to watch this spectacle. Need one more dazzling show? The city’s most stunning and important buildings are illuminated to spectacular effect every night, so wrap up and see them all from an open-top night bus tour.

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  2. Day 2

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    1. Morning

      Get a 360 view of Chicago (1 hour)

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      Visit the John Hancock Center and take in the morning rush from the observation deck of 360 Chicago. After riding the fastest elevators in North America to the 94th floor, you’ll have panoramic views of the entire city and Lake Michigan. You can skip the ticket line by booking in advance, and if your morning coffee hasn’t done its job yet, give yourself a jolt of adrenaline by upgrading your ticket to the TILT experience. Leaning out over Michigan Avenue from 1,000 feet will surely wake you up, right?

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    2. Shop the Magnificent Mile (1.5 hours)

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      From the Chicago River to Lake Shore Drive, the Magnificent Mile stretches along Michigan Avenue and is filled with upscale shopping, restaurants, outlet stores, and iconic buildings. See if you can pull yourself away from snapping photos of the historic Water Tower and Tribune Building, home to the city’s favorite newspaper, to head inside the chic department stores, jewelry boutiques, and gift shops. Star Wars and LEGO fans won’t want to miss the life-size model of Darth Vader greeting customers at the Water Tower Place store entrance.

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    3. Afternoon

      Indulge in a Chicago Red Hot (1 hour)

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      Coming in a close second to deep-dish pizza in the race for the most iconic dish of Chicago is the Chicago Red Hot –– a hot dog with chopped onions, pickles, mustard, relish, tomatoes, and peppers, nestled between a steamed poppy seed bun. There are plenty of hot dog stands and pop-up shops where you can grab a Red Hot, but Portillo’s in the River North District is one of the most popular, for good reason.

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    4. Let the Art Institute make an impression (3 hours)

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      From Matisse to Monet, O’Keefe to Pollock, you could spend an entire day exploring the 300,000 pieces of art throughout America’s second-largest art museum, the Art Institute of Chicago. This attraction draws big crowds, so you might want to pre-purchase tickets and skip the line. The museum is mainly known for its vast collection of impressionist and post-impressionist paintings — the most extensive collection outside of Paris. If that doesn’t impress you, entire exhibits are dedicated to American and modern art.

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    5. Evening

      Discover a darker side in the notorious Chicago Loop (1.5-2 hours)

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      Beneath the iconic skyline, Chicago’s streets tell a darker history of dangerous mob bosses like Al Capone and John Dillenger. Immerse yourself in their criminal history with a tour of the most infamous landmarks around the Chicago Loop area, south of the river. Dig deeper on this walking tour or, if your legs are done for the day, opt for the bus tour. Both options will take you to notorious locations such as the site of the St Valentine’s Day Massacre, the Clark Street Bridge, and Lincoln Park. Need a drink after the tour ends? Luckily, you’re well placed for a last meal at the Riverwalk’s restaurants before a nightcap in one of the luxury hotels or sophisticated cocktail lounges on either side of the river.

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