I’m always taken aback when I come to Chicago. My memories of visiting this city don’t seem to do justice to the stunning downtown skyline, the beautiful lakefront that seems to stretch forever, and the overall vibe and energy of the city that just pulls you in.
Known as The Windy City, Chi-Town, or Second City, Chicago has a bit of everything. It’s also the home to one of the World Marathon Majors, and this was the reason for our visit in October 2025. We had 4 days in total, including the day of the marathon, to squeeze in some site seeing, sports watching and of course indulge in some famous deep-dish pizza.
Where We Stayed
Chicago is a huge city, so there’s plenty of options on where to stay. If budget is not an issue and you are short on time, then staying downtown in the Loop would be advisable. But being there for the marathon, prices of hotels and even Airbnbs were more expensive than normal, so we opted to stay a bit outside the city, but still close to local transport.
We had a short 5-minute walk to a nearby bus with only a few stops to get to the L, which takes you directly into the city. Our total commute time was about 45 minutes. We found this incredible Airbnb in Jefferson Park where we had the entire second story of the house to ourselves. The neighborhood we stayed in was lovely with beautiful homes, super safe streets, and bonus they were all decorated for Halloween!
Getting Around
Chicago has a great public transportation system operated by CTA (Chicago Transit Authority) and it’s very affordable too. There is an official app (Ventra) for payments, but we had no issues just using contactless on our credit cards for all buses and trains. We also used Uber a few times when we were short on time.
I’d recommend buying an e-sim before you leave, so you have data while out and about – Airalo is a great option. Using the Citymapper app it was very easy to get around with public transport.
Architecture Boat Tour
The Architecture Boat Tour is one of the most popular and unique ways to explore the city and for good reason. It’s a front-row seat to one of the most architecturally rich skylines in the world, while cruising on the Chicago River. We booked tickets ahead of time through Shoreline Sightseeing and chose the 60 min tour departing from Navy Pier.
I would advise arriving a bit early for your tour to ensure you can choose the best seat!
I can’t speak highly enough about this tour. It was definitely the highlight of our trip. We were blessed with a gorgeous sunny day and the reflections off the buildings shimmered on the water which just made it more magical.
Chicago is the birthplace of the skyscraper, and the skyline showcases architectural styles ranging from Chicago School, Neo Classical and Art Deco, to Mid Century Modern and Contemporary. There’s over 150 years of architectural evolution along the river that you cruise past. The tour also gives some great history about the city and the architecture, and if you’re lucky, you’ll get some comedic commentary as well.
Willis Tower (formerly Sears Tower)
Willis Tower (formerly Sears Tower) has 110 stories and held the title of the world’s tallest building from 1973 until 1998. The draw to this building is the Skydeck located on the 103rd floor. From up there you can see up to four U.S. states on a clear day (Illinois, Indiana, Michigan, Wisconsin). Book ahead of time, as time slots will sell out. Once at the top, you can look out the floor to ceiling windows from all sides.
“The Ledge”
The top attraction is the glass balcony called “The Ledge” that extends out from the building allowing you to walk out and look straight down. There was a small queue we had to join to get our allocated time at the ledge. There are three different ledge boxes that are managed by staff who set a 90 second timer and help snap all those perfect Instagram photos. It’s actually pretty well organized, and we were more than happy with how our photos turned out. And if you want a 2nd attempt and more photos, then just rejoin the line!
Millennium Park
Opened in 2024, Millennium Park is a beautiful 24.5-acre park built on top of parking garages, railroad yards and other structures, which essentially makes it one of the one of the world’s largest “rooftop gardens.” The park is home to several iconic features like Cloud Gate (“The Bean”), Crown Fountain, Jay Pritzker Pavilion and others.
Cloud Gate aka “The Bean”
Probably the most well-known spot in the park is Cloud Gate aka “The Bean”. This polished mirrored modern art sculpture by Anish Kapoor is shaped like a bean and reflects the beautiful skyline of the city incredibly. Always a great spot for some selfies, but try and plan for a sunny day. And good luck trying to catch this place without a crowd!
Jay Pritzker Pavillion
Directly behind the bean is the Jay Pritzker Pavillion, an outdoor concert venue designed by renowned architect Frank Gehry. The design is quite modern with curving stainless steel ribbons that flow over the stage. The venue was designed to combine modern art with a public space for musical performances and home to the Grant Music Festival.
Crown Fountain
Adjacent to the Bean, you’ll see two enormous 50-foot LED screens facing each other across a shallow reflecting pool. This interactive modern art installation is the Crown Fountain. The screens continually display faces of different people, which looks stunning against the Chicago skyline. Watch out for the lips which spout water every few minutes.
There are several other beautiful spots within the park, so I recommend taking some time to walk around, enjoy a coffee or enjoy your lunch al fresco with the gorgeous skyline as your backdrop.
Grant Park
Grant Park is known as Chicago’s’ front yard because it’s where the city gathers. This 319-acre park stretches along Lake Michigan in downtown Chicago between the loop and the lake. This “front yard” is actually a collection of other hotpots that sit inside it, like Millenium Park, Art Institute of Chicago Museum Campus and Buckingham Fountain. Big events like Lollapalooza and the Chicago Marathon Finish Line take place here.
Buckingham Fountain
Do not miss walking by Buckingham Fountain as I think it’s one of the most beautiful spots in the city. It is one of the largest fountains in the world and is inspired by the Latona Fountain in Versailles.
Around the fountain are four sets of sea horses symbolic of the four states bordering Lake Michigan (Illinois, Wisconsin, Michigan, Indiana).
It’s hard not to be blown away standing in front of this majestic fountain against the backdrop of the city! We thought it was the perfect spot for an outdoor lunch stop.
Chicago Lakefront - Get on Your Bike!
Another thing that makes Chicago so special is the lakefront. This incredible 26-mile (42 km) stretch of public lakefront runs along Lake Michigan, from Hollywood Avenue (north) to 71st Street (south). The long stretch is almost entirely open to the public and takes you past Navy Pier, Lincoln Park, Lakefront Trail (runs full length of the lakefront), beaches (over 2 dozen), Museum Campus, Burnham Park and Promontory Point.
In my opinion the best way to see the lakefront is to rent a bike. There is a city bike share called Divvy with both classic pedal and e-bikes that you can rent by the minute. These are great for shorter trips, but if you want to ride further or bike around the whole city, I recommend renting a bike for the day. We rented a city bike with Bike & Roll Chicago near Millenium Park for just $35 for the day! We enjoyed riding from DuSable Harbor all the way to Montrose Beach – great exercise, beautiful views and sightseeing all at the same time!
Chicago Riverwalk
Prefer getting around on foot? Chicago Riverwalk is a much shorter walking path along the south bank of the Chicago River. It stretches for about 1.25 miles from Lake Shore Drive to Lake Street. It’s lined with many restaurants, bars, gardens, and some art installations. Many restaurants have terraces over the water or just on the water, so it’s some of the best up-close views of the skyscrapers and bridges you can get!
Thankfully, the spot we stopped at for a glass of wine also had outdoor heating lamps to help with the Chicago wind that can be so bitter sometimes! For something more active, it’s a lovely place to jog or rent a kayak to explore the river up close and personal.
Navy Pier
Navy Pier was completed in 1916 as part of the 1909 Plan of Chicago to emphasize open space and lakefront access. Originally named Municipal Pier No.2, it was built as a modern pier for freight ships to dock and transfer goods directly to the rail lines, but also as a public gathering place with promenades, gardens and events.
During World War I, it was used as a naval training center and hence became known as and was later officially renamed to Navy Pier. Today this 3,300-foot pier is home to shops, gardens, restaurants and various entertainment venues. You’ll also get some more great views of the city skyline.
Interestingly Chicago is where the first ever Ferris Wheel was opened to the public (at the World Expo in 1893). There is still a Ferris Wheel on Navy Pier, but it’s not that original one!
Flyover
Inside Navy Pier you will find one of Chicago’s newest attractions – the Flyover. This is an immersive experience that takes you soaring over several of Chicago’s iconic spots. And no joke you really do feel like you are flying over these, even getting sprayed with water mist as we flew over Lake Michigan. The tickets are $34 per person, so a bit pricey, especially given the short time of the experience. But that being said I still thought it was very cool, with views of Chicago you won’t get anywhere else!
Chicago Sports
Chicago is home to some of the most famous and legendary sports teams in the country, making it a true sports town at heart. From the Bulls and Bears to the Cubs, White Sox, Blackhawks, and Fire, Chicago’s teams have passionate fan bases and deep histories that are woven into the city’s identity. Whether it’s watching the Bulls play in the arena where Michael Jordan became a superstar or sitting in the stands with a hotdog and watching the Cubs play in one of the oldest ballparks in the country, Chicago is truly one of the great sport cities.
We were lucky enough to watch the Bulls play in a pre-season game while we were in town. Unfortunately, baseball season was over for both the Cubs and the White Sox, but we did go down to Wrigley Field anyway to check out the stadium and area.
Wrigley Field and Wrigleyville
Home to the Chicago Cubs, Wrigley Field is one of the oldest and most iconic baseball stadiums in the US. It’s known for its ivy-covered outfield walls, the old iconic red marquee, and historic hand‑operated scoreboard. This legendary stadium has been open since 1914.
While we couldn’t watch the Cubs play, we did enjoy walking around the stadium, visiting some of the souvenir shops and enjoying a drink in a local bar. Wrigleyville is a neighborhood that has its own vibe and character beyond baseball. There are several lively bars and restaurants, many filled with Cubs history and memorabilia (obviously) that make it a fun place to hang out!
The Chicago Marathon
The Chicago Marathon has been happening since 1977, and is one of the original World Marathon Majors. It ranks third in terms of participants with just over 54,000 finishers this past year (2025). The event is huge and the whole city turns out to support the runners along the route. I’m no marathon runner, but I was lucky enough to not only watch this incredible event but personally cheer on a runner! The day was great fun, migrating from spot to spot to cheer people on. We were extra lucky that the weather was warm and sunny on the day too.
The Chicago marathon is so popular, that most runners (unless you are elite and have the necessary qualifying times) will need to submit their application to a lottery and keep fingers crossed to get a spot! So, if you are interested get your application in!
Roof Top Bars
I’d highly recommend visiting some roof top bars to get some of the best views of Chicago’s skyline or the lakefront. Cindy’s located right on Michagan avenue has this incredible view of Lake Michigan and Millenium Park. And, they also have some delicious cocktails.
London House on the corner of North Michigan and East Wacker has the views of the skyline overlooking the Chicago River. Non reserved space up here is limited, so if you want to spend some time enjoying drinks and the view, I recommend making a reservation.
Chicago Style Deep Dish Pizza
I mean who’s going to come to Chicago and not indulge in some deep-dish pizza? It would be a crime not to enjoy a hearty, filled pie!
We had to go to the source and visit the restaurant that invented this tasty treat. The most widely accepted origin of deep-dish pizza is at Pizzeria Uno, which opened in 1943 in downtown Chicago at the corner of Ohio and Wabash. The founders Ric Riccardo and Ike Sewell wanted to create something more filling and unique than the thin, foldable pizzas common in New York.
My fun fact takeaway here is that Ike Sewell was not only a fellow Texan, but from a small town in Texas close to Dallas, my hometown! Okay back to the pizza – these things are very, very filling, so take that into consideration when deciding what size to order. We ordered a small and that was plenty for the two of us! They are made to order so the wait can take some time – but hey you can’t rush perfection!
Wrap Up
Our four days in Chicago were action packed, and I felt we did get to see and experience a lot. Booking tickets ahead of time for things like the boat tour, the Skydeck and the Bulls game were essential, and saved on time trying to sort this out on the go or worse having things sold out.
We were quite lucky with such warm weather consdering we visited in October. There is definitely more to see, and I wish I had another day to check out Lincoln Park or get tickets to the comedy at 2nd City. But that just gives me more of an excuse to come back, plus my bucket list won’t be complete without watching the Cubs play at Wrigley. Until next time Chicago!!
