24 Hour visit to Chicago: what attractions to see in one day
The Chicago skyline, Millennium Park and Lake Michigan. All photos by John O’Boyle / The Empty Nest Explorers
It’s easy to see many of Chicago’s major attractions during a one-day visit. Many of the must-see attractions are located in the downtown Loop area. The area is very walkable and visitor-friendly.
Recently we had a one-day business trip to Chicago to do some corporate portraits for one of our clients. We flew out the day before the photoshoot to spend an afternoon and evening enjoying some of the city's highlights.
We stayed right downtown within the Loop area (more on that later), a perfect hotel location from which to explore many of Chicago’s main attractions.
Table of Contents
How to get from O’Hare Airport to downtown Chicago
We decided to take the subway from the airport to our hotel downtown. The Chicago Transit Authority’s Blue Line operates 24 hours a day, 7 days a week. It was easy to navigate and took about an hour. You can transfer to other lines as needed, but the Blue Line will take you to the heart of downtown. The Blue Line can be accessed from all terminals at O’Hare, and the cost is $5 for the one-way ride.
The subway accepts tap to pay so payment is very simple.
Besides the train option, there are also taxis, buses, and van shuttle services available. These are considerably more expensive than the subway, and take about the same time. So we recommend the subway - it was easy and convenient.
Exploring inside Chicago’s Loop
When you think of Chicago, the Loop neighborhood is probably what you envision. It is the central business district of the city, the main section of downtown Chicago. It gets its name from the elevated rail that forms the hub of the Chicago “L” train system - which, confusingly, is also called the Loop (historically the Union Loop). The railway Loop is so named because the elevated tracks loop around a rectangle formed by Lake Street (north side), Wabash Avenue (east), Van Buren Street (south), and Wells Street (west), thus lending its name to that neighborhood, aka The Loop.
Still with me? Good.
The Northman Beer and Cider Garden, one of the many bars and restaurants along the Riverwalk.
After sitting on a plane and then a train for a while, a walk along The Riverwalk felt like just the right place to start to stretch our legs and take in the view. Given its central location, the Chicago Riverwalk is a natural focal point, bringing visitors and locals alike close to the Chicago River, the treasured waterway that flows through this area of the city. The Riverwalk pathway, which spans 1.25 miles and eventually leads to the lakefront, was constructed in phases over time and includes four distinct districts; The Confluence, The Arcade, The Civic, and the Esplanade.
Stairs lead down to this below-street-level walkway, where you can stroll along the river and admire Chicago’s signature architecture.
The walkway is lined with restaurants, bars, a beer garden, ice cream stands, shops, tour boat ticket pavilions, and kayak rentals. In nice weather, like the beautiful day, we lucked into, all manner of folks are out enjoying the sights. Knowing how cold Chicago can get (we both have freezing memories of visiting in March and October, separately), I imagine Chicagoans take full advantage of their outdoor spaces when the weather is good.
We ate dinner at Chicago Brew House and sat directly on the railing at the river’s edge. Since we were in Chicago we decided to order a classic Chicago-style hot dog and a sliced beef sandwich. Both were excellent and the service was very attentive too.
You will not find fine dining at most of the restaurants and bars along the Riverwalk but they offer solid pub food, a wide drink menu, and a fun location.
Boat tours are extremely popular - we saw more sightseeing cruises than we could count as we strolled along the river. There are many providers of these tours, and no wonder; with its two stunning waterfronts — both the Chicago River and Lake Michigan — the water is one of the best ways to see the city.
There are numerous options, depending on your interests and adventure level. You can opt to admire the skyline on a lakefront cruise or learn about the city’s iconic architecture on a Chicago River cruise. There is also a dinner and dancing cruise aboard an all-glass vessel, a tiki-themed boat for cocktails on the water, yacht cruises, and speedboat rides - the options are endless! Or you could always simply choose to be your own captain and paddle your own kayak.
There are many ways to enjoy the Chicago River. Seen here are a kayak rental, a motor boat rental and a large sightseeing cruise boat.
Visiting Chicago’s Navy Pier
Chicago’s Navy Pier is a fun location on the Lakefront with beautiful views of Lake Michigan. It is the home of many public events and exhibits, as well as renowned restaurants, parks, rides & attractions, and is a major cruise departure point. It’s a little touristy, but it has some iconic features, like the Billy Goat Tavern and the giant Centennial Wheel ferris wheel ride. Many walking tours pass through the area, and in summer it is host to live music events, fireworks, and theater productions - well you get the idea.
The Chicago Explorer Pass, available through the Go City app, gives you access to the attractions at Navy Pier, plus another 25 attractions and activities in Chicago at a discounted price.
Navy Pier is the location for Wednesday and Friday night fireworks during the summer.
Experiencing Millennium Park in The Loop District
We really enjoyed our walk through Millennium Park, the large lakefront green space that features many unique attractions. We passed the Jay Pritzker Pavilion & The Great Lawn where a community movie viewing was taking place. The unique curved stainless steel structure is the site of live entertainment, with a state-of-the-art sound system designed to mimic the acoustics of an indoor theater, and concert-goers can sprawl on the lawn for a great outdoor experience.
The beautiful Lurie Garden features award-winning botanical landscaping for all seasons. Utilizing native perennials and bulbs, the garden creates a haven for wildlife, birds, and insects. We were happy to get there as the sun was setting for low photo angles of the sun through the summer flowers.
Bird Nerd Alert - For my birding friends, there were signs telling visitors that Red-winged Blackbirds were nesting in the garden, so beware of a protective swoop by a dutiful mama or papa redwing! We didn’t get swooped but we did have a close encounter with a singing male atop a bloom, and that made me smile. Nice to know that beautiful wildlife is thriving in the heart of an urban environment like downtown Chicago.
Of course, we visited Cloud Gate, aka “the Bean”, the reflective blobular sculpture that’s so popular on Instagram. I have to admit, though I don’t generally buy into that type of forced tourist experience, the Bean is actually pretty cool. The visual illusion of the mirrored surface is fanciful fun. We could see it the next day from the skyscraper window where we were working. ;)
In front of the Bean is the McCormick Tribune Plaza & Ice Rink. Since we visited in July, the ice rink was converted into a pretty outdoor dining space, The Park Grill, which we thought was a great way to multi-use the space.
Our favorite spot in Millennium Park had to be the Crown Fountain. It’s just a simply joyful public attraction. Two giant pillars of glass blocks loom at each end of the shallow fountain pool, and intermittently project videos of the faces of Chicagoans.
Kids splash in the large fountain area and every so often, water is sprayed out of what appears to be the mouth of the giant faces. What fun! If I had had a change of clothes, I might have just jumped in with the kiddos! Even older folks were enjoying themselves sitting on the benches along the sides, keeping cool with the spray from the fountain.
Chicago’s Crown Fountain
There was more to the park than we were able to see for ourselves, including children’s play garden and outdoor art galleries. Overall, we would highly recommend making Millenium Park part of your Chicago experience, especially if you have limited time in the city as we did. It definitely gives you a good feel for the city culture, as it is certainly used by locals and tourists alike.
Visiting Chicago’s Museums
In the heart of downtown, adjacent to Millenium Park, sits Chicago’s best museum, the Art Institute of Chicago. The Institute was founded in 1879 as both a museum and school for fine arts. This was a critical time in Chicago’s history, as the focus was on rebuilding the city that had been destroyed by the Great Fire of 1871.
The museum has grown in size and reputation over the years, and now houses the greatest collection of Impressionist paintings outside of Paris. The most recent addition is the Modern Wing which was opened in 2009. There are two entrances to the museum: the doors to the original building are at 111 South Michigan Avenue, and the entrance to the Modern Wing is at 159 East Monroe Street.
The Modern Wing of the Art Institute of Chicago
If you don’t have a lot of time to spend, the Art Institute's website offers a “what to see in an hour” page, listing some of the most celebrated works that you won’t want to miss and what gallery to find them in. This list includes one of Van Gogh’s self-portraits, Hopper’s original “Nighthawks”, and Picasso’s “Old Guitarist”, to name a few, as well as works by current Chicagoan artists.
Further south and directly on Lake Michigan is a beautiful green space known as Chicago’s Museum Campus. It is home to three of the city’s most popular museums. The first is The Field Museum, a natural history museum containing artifacts spanning thousands of years, including the largest dinosaur ever discovered, Maximo the Titanosaur.
Right next door is the Shedd Aquarium, one of the largest aquariums in the world, boasting 32,000+ aquatic creatures, including beluga whales, dolphins, sea otters, sea lions, penguins, stingrays, and sharks.
The last museum of the campus triad is Adler Planetarium. It opened in 1930, as the first planetarium in the Western Hemisphere. Visitors can experience interactive exhibits, live planetarium shows, hands-on educational programs, and world-class collections.
Visiting Downtown Chicago Loop Retail Historic District
If museum visits are not your thing or just don’t fit into your timetable, a walk through the Loop Retail Historic District may be a more doable way to get your dose of art and culture. This area is chock full of historic buildings and landmarks. It was added to the National Register of Historic Places in 1998, boasting 74 contributing buildings and structures.
The district is most commonly associated with department store buildings, due to the seven prominent department stores that it hosted in its heyday; six of these buildings are still standing. Most significant is the Marshall Field’s building, which now houses an 8-floor Macy’s that ranks as the second largest store in the world. So if you need to do some shopping, this might be fun to check out.
The interior features a Tiffany & Co. vaulted ceiling and several balconied atria. But even if you don’t go inside, the two huge vintage Great Clocks on each corner of the building along State Street are worth seeing. The clocks were installed to encourage punctuality, as people in the early 1900’s used the store as a meeting place, loitering about, often leaving notes for companions in the windows of the store. That sounds somewhat romantic to me - imagine hurrying to the store and finding your special note!
Other significant buildings in the district include the Joffrey Tower, Palmer House, Page Brothers Building, and the Chicago Theater.
Visiting the Willis Tower (Sears Tower) in Downtown Chicago
Of course, while admiring the Chicago skyline, one can’t miss the Willis Tower, the sleek tiered black skyscraper that looms over all the others. It used to be known as the Sears Tower (more retail!) and held the bragging rights of being the tallest building in the world until the late 1990s when it was surpassed by several others. The observation deck is still the highest in the US though, at a dizzying 1,353 feet from the ground.
You can actually feel the building sway in the wind! It is a very well-done observation deck, surrounded by large windows for breathtaking views of Chicago and Lake Michigan.
And if you are feeling even more adventurous, step out onto The Ledge - a glass-walled and glass-floored box that extends four feet from the building, where you can feel as if you are floating 103 stories above the ground. This feature is much better realized than a similar feature at The Summit at One Vanderbilt in NYC, in our opinion. Although there is a queue to experience it at both places, at The Summit, visitors are made to look up at a camera to get a photo taken with their backs to the view, which makes no sense, since they have to move right along after the photo and don’t really get to turn around and experience the suspended illusion. At Willis, visitors get more of a chance to enjoy it without the silly canned photo, which we feel is a better implementation. So that’s a point for Chicago. ;)
Advanced tickets through their website are highly recommended for the Willis Tower, as it is a very popular attraction.
Best guided tours in Chicago
If you only have 24 hours in Chicago you might want to consider a guided tour to make the most of your time. Here are some of the best options:
The wonderful view from our room at the Westin Chicago River North. The hotel is located directly along the Chicago River and is close to all of central Chicago’s attractions.
You can find more info and rates here.
Chicago River tour
See more than 40 buildings including the Wrigley Building and Willis Tower
Lots of options, tour runs more than 20 times daily from Navy Pier and Michigan Avenue
Live commentary on board
Book the Chicago River tour here
Food, History and Architecture Walking Tour
Overview of the city and major attractions
Sample food including Chicago-style hot dogs, Pizza, and Italian Beef
Book the walking tour here
Gangsters and Ghosts Tour
Learn about gangster-era crime in “The Loop” area
Visit Palmer House Hotel, rumored to be haunted
Visit Congress Hotel, Al Capone’s headquarters
Book the Gangster and Ghost tour here
Note - This blog post contains affiliate links. This means that if we are recommending a product, activity, or hotel, we might be receiving a small commission if you buy or book from these links. This is done at no additional cost to you. We only recommend products we have personally used or have thoroughly researched.
Go City Pass
If you plan to see multiple attractions during your trip a Go City Pass might save you money.
Take a look on their website and see. Click here.
View of the Chicago skyline, including the Willis Tower
This post was researched and written by Debbie of the Empty Nest Explorers. You can learn more about the Empty Nest Explorers here.
Some well-reviewed Chicago tours:
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