If you’ve only got 48 hours to enjoy one of the world’s most exciting cities, then knowing the exact places to visit in Chicago is vital knowledge. Thankfully, we love sharing our top tips for things to do in Chicago, so rest assured you’ll be going to the best landmarks, restaurants and attractions with our guide.

Here’s your whistle stop tour for the Windy City…

DAY 1

Checked in? Now check your bearings

You want to know where you’ll be adventuring tomorrow. Well the good news is that 360 Chicago at the John Hancock Center stays open till late, with the last admission at 10:30pm. So, once you’ve settled in at your hotel, come on over to North Michigan Avenue and look out over the city. Magnificent Mile? Check. Navy Pier? Check. And you can’t miss Lake Michigan. Get ready, you’ll be visiting them all very soon.

Red Route, Stop: 360 Chicago


Go for a morning stroll

Now you’ve unpacked, have you packed something comfy for the day ahead? Don’t worry, we’re sure you’ll be able to buy some replacement sports gear in Chicago. Especially somewhere along the Magnificent Mile, one of the best shopping strips in the US, if not the world. There are 13 blocks, and around 460 world-class stores along this stretch of North Michigan Avenue.

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Red Route, Stop: The Water Tower


Time for lunch

There are plenty of expensive eateries along the Magnificent Mile, and lots of fast food joints too. But why not aim for somewhere in the middle? The Purple Pig is a wine bar located at 500 N Michigan Avenue that has lots of dishes and snacks featuring, you guessed it, pig. It’s great fun, but don’t fill up too much. You’ve got a busy day ahead.

Red Route, Stop: The Water Tower


Take a Lakefront Speedboat Tour

Now head east towards Lake Shore Drive. If you’re a culture vulture, why not stop off at the Museum of Contemporary Art on E Chicago Ave, with its up-to-the-minute art installations? But if you prefer something a bit faster paced, come over to Navy Pier and hop on the Seadog Chicago for a seabird’s view of Chicago. You’ll speed past the waterfront and see some of the tallest buildings in the world.

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Red & Blue Route, Stop: Navy Pier


Watch the sunset on Navy Pier

Disembark at Navy Pier and wander through it, taking in its sights and sounds. Grab a seat on the huge Ferris wheel, or just take your time strolling the waterfront. And now it’s time for an evening bite. How about Riva, with glorious seafood and steaks, plus a superb view of the waterfront?

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Red & Blue Route, Stop: Navy Pier


Have a laugh before bed

After dinner, we recommend a visit to The Second City, where you can watch live improv and perhaps catch the next Steve Carell or Tina Fey making their comedy debut. First starting in 1959, the night has gone on from strength to strength and takes the accolade for being home to the first ever on-going improvisational theatre troupe based in Chicago.

DAY 2

Start at Millennium Park

Welcome to the start of day two. After breakfast, head on over to Millennium Park to experience one of the world’s most dynamic and vibrant public places. You’re sure to catch some live music or interactive art while you’re here. If you’re staying north of the river, swing by Michigan Avenue Bridge on your way. This double-decker bridge is one of the most photographed landmarks in America.

Red Route, Stop: Millennium Park & Palmer House Hilton


Feast on Chicago pizzazz and pizza

Time for lunch. Why not try Giordano’s Pizza in the Loop, near Willis Tower? You’ve got to try the deep dish 'Chicago-style' spizza while you’re here. And if you’re wondering what makes this Chicago cheap eat so special, it’s all to do with the pan in which it is baked. It gives the pizza its characteristically high edge creating lots of space for large amounts of cheese and a chunky tomato sauce. Yum.

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Red Route, Stop: Willis Tower & Skydeck Chicago


Take the Chicago Crime Tour

If you’d like to learn about the Windy City’s notorious criminal history, jump on the Chicago Crime Tour's luxury limousine bus to journey through River North, Gold Coast, Lincoln Park, Old Town, Loop and Magnificent Mile neighborhoods. You'll hear stories of Chicago's dramatic criminal history, see infamous crime scenes, and learn more about villainous gangsters like Al Capone and John Dillinger.


Choose between planets and aquatics

If there’s still time, we recommend a trip to the waterfront to visit Adler Planetarium, with its interactive space travel experiences. If possible, pay a visit to the Shedd Aquarium next door too — it's home to over 1500 different aquatic animal species.

Red Route, Stops: Adler Planetarium and Museum Campus


Enjoy your final night out

Right, let’s go for it. If you want to dance to some big sounds, we recommend The Mid in the Fulton Market area of town – get here early to get your place in the line. But if you just want a final Chicago meal you’re going to remember, head over to Alinea for a gastronomic feast you’ll never forget.

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Red Route, Stop: Museum Campus

With our itinerary in tow, 2 days in Chicago is plenty of time to experience all of the best highlights. Get your fix of Chicago landmarks and attractions on the top deck of our open-top Big Bus tours too, it’s the easiest and most interesting way to see all of the iconic sights if you’re only in the Windy City for a couple of days.