How to Spend 48 Hours in Chicago
'The Windy City' will certainly take your breath away, as you'll fall short on time but not on experiences and attractions.
Chicago will surprise you with every turn you take and every discovery you make, with a treasure trove of museums, skyscrapers, parks, cafes, and entertainment hubs. However, it takes planning and prioritising for a two-day trip, as there's so much to do here. If you've just finished summer camp, you'll likely need to speed round.
Worry not; we've got you sorted. Keep reading to find out how to make the most of your 48 hours in Chicago, which can be the most fun 48 hours of your trip.
Day 1
Early morning: Skydeck Chicago
Get an early morning dose of Vitamin D and some ultra-dizzying 360° views of Chicago's topography as you set your foot on Skydeck Chicago.
Skip the long queue by rising up early, getting breakfast on the go, and enjoy the ride to the 103rd floor of the Willis Tower, where the Skydeck (or Willis Tower Observation Deck) is situated. The world-famous retractable balconies (also called the Ledge) offer a complete view of South Wacker Drive. In case you're too scared to get into one of these, the observatory still commands almost surreal views of Lake Michigan and the plains of Illinois.
After you've spent a good time looking from the third-largest building in the USA, you're ready to move on to something else in the morning.
Early afternoon: Millennium Park
The sprawling Millennium Park is just a short ride away from Skydeck Chicago, with public transport taking about 15 minutes.
Loaded with a myriad of attractions, Millennium Park will take your breath away at first glance. You can splash around the Crown Fountain, or take pictures with the famous Bean or Cloud Gate. To enjoy moments of peace and solitude, you can head to the serene Lurie Garden, whereas adventure fanatics can opt for rock climbing at Maggie Daley Park.
Grab a quick bite from the nearby Plaza at Park Grill before leaving for your next location.
Late afternoon: Shedd Aquarium
Shedd Aquarium is a fun way to spend an afternoon in Chicago.
This indoor experience (combined with a 4D theatre) will keep you intrigued throughout. The underwater exploration will take you through several exhibits, such as the Caribbean Reef, Amazon Rising, and Oceanarium, giving you a sneak peek into all types of marine life. This is also your chance to meet friendly sea creatures such as penguins and dolphins, so don't forget to say hello!
Note: Make sure to buy your tickets in advance and have enough time in hand, as the Aquarium closes at 5pm. Before you leave, take a look at the cute collection of the souvenir shop (it's the penguin toys for us).
Evening: Chicago Riverwalk
As soon as you're outside, Chicago transforms into a different version of itself, and there is no place better than the Chicago Riverwalk to experience the magical dusk of Chicago.
The Riverwalk is a sunset enthusiasts dream, lined with restaurants, bars, museums, public art, and boat rides. Even if you decide to take a simple walk alongside the river, you won't be disappointed, as the Riverwalk is perfect for spending a light-hearted evening.
If you feel like staying back, you can dine in a nearby restaurant, and after you are done, the starlit night is all yours.
Day 2
Early morning: Navy Pier
Navy Pier is a place that goes into celebration as soon as summer arrives.
So, for day two, the first place to kickstart your day is going to be Navy Pier. Overlooking the shimmering waters of Lake Michigan, an early morning ride to Navy Pier is a therapeutic one. Sharing a glimpse of the whole city in parts, Navy Pier can be a chilled corner of Chicago before it finally wakes up and gets busy with everyday hustle and bustle. If you go later in the day, the 200-foot tall Centennial Wheel and Pier Park could be a great idea. Still, in the morning, boat cruises, bus tours, or simply a breakfast trip could be a perfect choice.
During summers, visiting Navy Pier at night is a must, and you don't want to miss the annual fireworks if you're there at the same time.
Late morning: Polk Bros Park
After a beautiful start at Navy Pier, head to the Polk Bros Park to catch a few minutes of peace.
Get a seat near the fountain and just relax as the sun shines down, or take off for the Polk Bros Park Performance Lawns and catch stunning views of the skyline and the lake. By this time, you could even nip back to the Navy Pier and go and take a ride on the Centennial Wheel, which is a short walk away.
Early Afternoon: The Art Institute of Chicago
Next up is one of the oldest institutes of the world; the Art Institute of Chicago.
Housing iconic pieces like Pablo Picasso's The Old Guitarist and Grant Wood's American Gothic, it is also a present time institute, nurturing budding artists.
Artistic works ranging from Byzantine to contemporary ages make the Art Institute of Chicago a worthwhile place to visit for those captivated by art.
Before leaving the penultimate destination of the day, make sure to check out the souvenir collection and pick something that will always remind you of your 48 hours in Chicago.
Afternoon: Chicago's Water Tower Place
The last stop for today is the massive Water Tower Place, which has to be on everyone's list.
This entertainment hub is a mecca of clothing retailers, theatres, sports museums, and eating outlets. Water Tower Place also lies close to the Magnificent Mile commercial zone and mall, a heaven for shopping lovers. But in case you aren't one, there are enough little cafes to take a minute to chill, and enough eateries to sign off your time in Chicago with a yummy flourish.
With so much to do in the Windy City, this 48 Hours in Chicago guide just scrapes the surface of what you can do in this incredible city. From their famous basketball history to other stunning landmarks dotted around, Chicago will captivate anyone who visits.
Additional tips
- The best way of getting around Chicago is the L train. It connects most of the city (and the airport) and is an easy-to-use transit system. For those that prefer buses, Chicago also has an extensive bus network that connects nearly every major landmark in the city. For each, you can pay individually for journeys, but to save money, your best bet is to get a day or multi-day pass, allowing you to tap on easily and save money simultaneously.
