Chicago has it all – beaches, skyscrapers, iconic structures and world-class museums. If you’ve only got 3 days in the windy city, you’ll need a perfectly-planned itinerary to make the best of your time and squeeze in as much as you can.

Here are our suggestions of how to do all your sightseeing in Chicago in 3 days…



Dedicate your first day in the city to ticking off Chicago’s biggest sights and attractions so you don’t miss out on anything. Take a guided bus tour around all of the major landmarks and you’ll get your bearings along with a great introduction to the city.

Some of the iconic locations you’ll pass by include the Willis Tower, Millennium Park, Navy Pier, Grant Park and Museum Campus. Your tour guide will bring the city to life with all the information and trivia you need. And, they’ll offer tips on how to spend the rest of your time, pointing out the local hotspots and lesser-known sights.

Hop off at any attractions that take your fancy to get a closer look. We recommend Millennium Park to take a selfie at the shiny, bean-shaped Cloud Gate sculpture. If it’s a nice day, stroll along Navy Pier and enjoy the rides and outdoor attractions. There’s even a one-acre, botanical garden inside the pier. Or, stop off at the 1,353-foot-high Skydeck to enjoy 360 degree views of the entire city. If you don’t mind heights, brave ‘The Ledge’ – a glass balcony that extends four feet outside the building that you can walk along.

Skydeck Tickets

Find the nearest Big Bus Stop to Skydeck


A city with so many skyscrapers and iconic buildings can only look equally as amazing at night. Join a night tour and discover Chicago after dark. You’ll see the entire skyline lit up and get a taste of River North’s vibrant nightlife.  

Or, if you want to make your night time sightseeing experience extra special, treat yourself to a Chicago Helicopter Experience. The 15-minute flight will take you on a magical journey across the illuminated city skyline and over the Willis Tower, the Magnificent Mile, the Tribune Tower, and more. Your pilot will provide an informative commentary and sightseeing tips as you enjoy the view and take endless photos.

Chicago Helicopter Experience Tickets



Discover a different side to the city by taking a walk along the 606 – Chicago’s answer to New York’s High Line. The former railroad has been converted into an elevated garden that you can walk or cycle across. You’ll pass through Logan Square, Humboldt Park and West Town on your journey, along with some of city’s best restaurants and bars that you can stop at on the way.

If you want to learn more about Chicago’s culture and history, hit the museums and galleries. The Museum of Science and Industry is one of the biggest in the world – it’s spread out over 14 acres with loads of interactive exhibits including a 40-foot indoor tornado and geometric mirror maze. There’s also a Museum of Contemporary Art, a Chicago History Museum, and an Art Institute of Chicago. If you’re a space fan, don’t miss the Adler Planetarium where you can star spot at the Doane Observatory and browse the space instrument exhibits.


You can’t visit Chicago without feasting on (at least) a slice of their famous deep-dish pizza. These deep-pan Chicago-style pizzas are more like pies, with a thick, high-edged crust and a generous cheese and chunky tomato sauce filling. Head to Pizzeria Uno which is where the deep dish pizza was invented in 1943, or Pequod’s Pizza, a hit with the locals.



Ticked off all of the major city landmarks and attractions? It’s time to hit the beach! It’s not often you get a holiday where a buzzing city and a beautiful beach are in such close proximity after all. North Avenue Beach and Oak Street Beach are the most popular summer spots, with gorgeous views of the city skyline in the background. If you want somewhere a bit more secluded, head to Helen Doria Beach which is uncrowded and away from the main areas.

Find the nearest Big Bus Stop to North Avenue Beach

If the weather isn’t beach-appropriate or you’d rather do something a bit different, head to SNL: The Experience for your third day. You’ll find it in Chicago's Museum of Broadcast Communications, and the interactive experience involves taking a journey through a week in the life of SNL production. You’ll start off with a meeting in Lorne Michaels' office and then experience the writing workshops, rehearsals, costuming and final show. You don’t even have to be an SNL fan to enjoy this fun and unique experience.

SNL: The Experience Tickets

Find the nearest Big Bus Stop to the Museum of Broadcast Communications

Sorted for your Chicago trip? The city offers so much, it’s hard to see and do everything in a short amount of time. But, follow the above Chicago itinerary and you’ll pack in a lot and get a great introduction to the city.