The Best of the Windy City: One Day in Chicago

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Rising from the shores of Lake Michigan, Chicago is bursting at the seams. World-renowned museums, awe-striking architecture and a food scene to rival any mean a visit to the third largest city in the U.S. is always a good idea.

The birthplace of deep dish pizza and steel-framed skyscrapers, Chicago is possibly best known for its history of organized crime. Thankfully, the days of gangsters ruling the streets are long gone, but their legacy lives on. On the big screen, scenes of Chicago were brought to our homes by Home Alone, The Blues Brothers and, of course, Chicago itself.

Whatever is drawing you to Chicago, you won’t be disappointed. A sprawling multi-faceted metropolis, Chicago really needs to be on your U.S. bucket list. Whether your ideal day in the Windy City is spent ambling along the lakeshore, delving deep into its museums, splurging on designer goods, soaking up the sights or a mix of them all and more, you’ll be amazed how much you can do with just one day in Chicago.

When to Visit Chicago

With a great mix of indoor and outdoor activities, there really is no bad time to visit Chicago. Being situated in the Great Lakes region, winters can be cold with frequent snowfall and temperatures often dropping below freezing. Visiting in winter isn’t a bad idea though, especially in the run up to Christmas. Chicago is one of the most festive cities in the U.S.; just remember to wrap up warm. Hotel prices also tend to be lower in the winter months.

Summers are mild with the warmest months being June, July and August. Visiting in summer is perfect for boat trips on Lake Michigan, gazing up at the stunning architecture and taking part in outdoor events.

Is the Windy City really that windy?

Despite the name, Chicago isn’t the windiest city in the U.S. That title actually goes to Dodge City, Kansas. In fact, Chicago’s average annual windspeed is lower than Boston’s. What earned Chicago the nickname the Windy City is the wind tunnel effect caused by wind blowing from Lake Michigan being channelled between skyscrapers.

Interestingly, there are several other theories relating to the nickname which don’t involve the weather at all. One claims that the name originated due a baseball rivalry with Cincinnati, but my favorite is that journalists from New York inflicted the name because of the amount of hot air coming from Chicago politicians’ mouths.

One Day in Chicago

9 am: Breakfast in Marina City

Chicago is known for its food, so the only way to kick start your one day in Chicago is with a breakfast to remember. Head to Yolk in Marina City on the north bank of the Chicago River. This vibrant, modern brunch spot is all about eggs, just in case the name didn’t give that away. Fried, scrambled, poached or in an omelette, however you like your eggs in the morning, you’ll like Yolk’s.

If eggs aren’t your style, Yolk’s selection of sweet specialities certainly don’t disappoint. From pancakes and waffles to freshly baked cakes and French toast, you’ll be spoiled for choice. Yolk are open every morning from 7am, so if you want to start early and get even more from one day in Chicago, you won’t have to start hungry.

10 am: Admire architecture from the river

Even more famous than its food, Chicago’s architecture is simply staggering. Home to one of the most diverse and innovative collection of skyscrapers in the world, Chicago was built with practicality in mind. It may be the third largest city in the country, but even here, space is limited. The best solution: build upwards.

Chicago’s first skyscraper, the Home Insurance Building, was built in 1885. At just ten stories high, it was the first building to use a structural steel design. In the decades which followed, hundreds more followed, getting taller skyscraper by skyscraper. Today, the Willis Tower takes the title of Chicago’s tallest. At an incredible 110-stories, it certainly dwarfs the Home Insurance Building.

A great way to see the tower, along with countless other Chicago architecture highlights is to take a cruise on the Chicago River. I love this 90 minute guided architecture cruise which departs from the foot of the Wrigley Building. It’s an efficient and relaxing way to learn a little more about the city’s unique design. If you’re running tight for time, a 45 minute option is also available.

12 pm: Chicago Riverwalk

Back on dry land, cross DuSable Bridge, named in memory of Jean Baptiste Point du Sable, one of the founders of Chicago to join the Riverwalk. Follow the path east towards the mouth of the river. If the cruise has fuelled your thirst for architecture, pause at the Chicago Architecture Center to learn even more. When you reach Lake Shore Drive, cross FDR Bridge to DuSable Park for a stunning view of the harbor.

1 pm: A lakeside lunch at Navy Pier

Built in the midst of the First World War to accommodate freight boats and passenger steamers, it wasn’t until the early days of the Second World War that Navy Pier gained its name when it was transformed to a naval training center in 1941. When the war drew to a close, the pier served briefly as a university and later returned to commercial use.

If you’re spending one day in Chicago with young children, don’t miss the Chicago Children’s Museum at the foot of the pier. An immersive interactive museum, it has everything from dinosaurs to a climbing schooner.

The Pier is the ideal place to pick up some souvenirs and grab a quick lunch. Dozens of cafes and restaurants line the building. For the best view, head to Offshore Rooftop at the pierhead.

During summer months, Navy Pier is the starting point for sightseeing cruises on Lake Michigan. These offer some of the finest views of the city and are a highlight of any trip to the Windy City. If you have time for a leisurely lunch, I strongly recommend this 2-hour gourmet cruise which tastefully combines gastronomic delights with Chicago’s iconic views. With just one day in Chicago, this half-hour speedboat tour is the perfect way to enjoy the sweeping vista of the city without compromising on time.

3 pm: Chicago from above

In keeping with pretty much every U.S. city, Washington DC being a notable exception, Chicago has more than its fair share of observation decks. Whilst the Willis Tower’s Skydeck is the highest and most famous, we recommend checking out 360 Chicago instead.

Not only does 360 Chicago offer shorter wait times and far better value, its proximity to Lake Michigan means the view is unrivalled. From the 94th floor, you can see the city unfolding beneath you whilst gazing down upon Navy Pier and Lake Shore Drive. What’s more, it’s perfectly situated for the next stop on our one day in Chicago itinerary: the Magnificent Mile.

4 pm: The Magnificent Mile

Chicago’s most famous street, the mile-long stretch of North Michigan Avenue from the Chicago River to the Near North Side is home to some of the city’s most iconic landmarks. Walk south along the Magnificent Mile, first passing the historic Water Tower then the Allerton Hotel before reaching the Tribune Tower on the banks of the river.

Magnificent Mile’s biggest draw is its shopping. High-end department stores, including Bloomingdales and Sachs Fifth Avenue line the street along with designer boutiques. Home to Ralph Lauren’s largest store, iconic brands such as Tiffany & Co., Bulgari and Cartier, this certainly isn’t the place to be hunting for bargains. If shopping is thirsty work, stop by the Starbucks Reserve Roastery, the Seattle coffee giant’s biggest outlet.

6 pm: A Slice of Chicago

It may be one of the simplest dishes around, but no day in Chicago would be complete without sampling the Windy City’s most loved food. Deep dish pizza was invented here in 1943 by Rudy Malnati, a chef at Pizzeria Uno. His son Lou, who followed in his father’s footsteps working at Pizzeria Uno, later opened his own restaurant: Lou Malnati’s.

Both now operate several restaurants in Chicago and beyond. The age old question: which is better? In truth, there’s probably very little difference but if you want to try the original, Pizzeria Uno is the place to go. Uno has a location two blocks from the Magnificent Mile on East Ohio Street, whilst the nearest Lou Malnati’s is beside the Wrigley Building where the Mile reaches the river.

7.30 pm: Catch a show on Broadway

Broadway in Chicago comprises five theatres, three of which are located in The Loop. One, the Broadway Playhouse is just off the northern end of Magnificent Mile whilst the Auditorium is in Downtown. Up-to-date show listings and ticket sales are available on the Broadway in Chicago website. 2025 highlights include Tina – The Tina Turner Musical, Beauty and the Beast, Moulin Rouge and Riverdance 30.

10.30 pm: A nightcap with a view

For the perfect ending to your one day in Chicago, head to LH Rooftop at the London House Hotel. On the southern bank of the Chicago River, directly opposite the Wrigley Building, Tribune Tower and the towering Trump International Hotel, this cosy heated rooftop bar is the ideal spot to unwind.

Where to stay if you have more than one day in Chicago

Whilst our one day in Chicago itinerary showcases the city’s highlights, this is Illinois’s biggest city, and there’s plenty more to see. Luckily, if you want to stick around to see it all, Chicago has no end of quirky boutique hotels.

For the ultimate Windy City experience, opt for one around the Magnificent Mile or the Chicago Loop. Our top pick is Hotel Saint Clair, conveniently located just off the Magnificent Mile. Designed in art-deco style, the rooms are bright and modern and their cooked-to-order breakfast is exceptional. Also on East Ontario Street, Ivy Boutique Hotel is the perfect mix of comfort and value. Their rooftop terrace and fantastic restaurants seal the deal.

If you prefer to stay in The Loop, the River Hotel should be your first choice. This classic riverfront hotel has recently been given a fresh lease of life under new management. It’s well worth paying a little more for a room with a view of the Chicago River, some of which overlook the Wrigley Building. Just south of the river, on North Michigan Avenue, Arlo Chicago boasts modern rooms with simple yet stylish décor along with a superb cocktail bar.

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