2 Days in Chicago: Plan the Perfect Trip to the Windy City

Know all about our two-day stay in Chicago and what we did as a first-timer in the city, along with hotel recommendations, must-try things to do and eat, and more to help you plan your ultimate budget adventure to Chicago!

One early summer afternoon, Abhi and I were watching The Bear, a Chicago-based show on Hulu. As we immersed ourselves in the vibrant scenes of the city, it struck us—we should plan a trip to Chicago. Excitedly, I started looking for flights. Fast forward to September, and we found ourselves on a plane, ready to explore the Windy City.

Our five-day sojourn began in Chicago, followed by a day trip to Milwaukee, and concluded with two memorable days at Niagara Falls, Ontario.

In this blog post, I’ll share details about our two-day adventure, including the best attractions, delicious food, flight and hotel details, and some exciting day trips you can take if you have an extended stay.

It was my first time in the city and Abhi’s second visit, so I let him pick activities that would give me a complete view of Chicago as first-timers. Here’s how it went.

Reaching Chicago from Seattle

Flight is the best mode to reach Chicago from Seattle, with plenty of non-stop flights between these two cities for under $200 per person round trip. Alternatively, you can also take the Empire Builder train, starting from Portland (Oregon), which takes two days to reach Chicago. It is considered one of the most scenic routes in the USA, passing through various cities and a National Park.

We took the American Airlines flight to Chicago from Seattle, which was 4 hours long with a time difference of 2 hours. It was a red-eye flight, and we were super tired the next day. But that didn’t dampen our spirits to explore the city. The cost of our one-way flight was $100 per person since our return was from a different destination (Buffalo, NY).

Top Spots We Visited in Chicago

Lincoln Park

Lincoln Park is a charming neighborhood in North Chicago known for its beautiful green spaces, historic architecture, and vibrant ambiance. The Lincoln Park Zoo and Conservatory are among the most prominent attractions in the area. Additionally, there are numerous trails around the park, from beach walks to garden paths, offering a glimpse into the city’s diverse landscape.

We were staying at the Chicago Getaway Hostel in Lincoln Park, so we decided to begin our adventures, exploring the largest park in Chicago, Lincoln Park.

North Pond

I’m sure you all know how much I love birds, so we decided to begin our exploration from North Pond, a beautiful 13-acre natural area, home to diverse flora and fauna. The trail was nice and easy with water on one side and lush gardens on the other. We spotted birds like the Great Blue Heron, American Robin and Juncos, and a few eastern fox squirrels.

North Avenue Beach

We then booked a cab and headed to the southernmost tip of Lincoln Park, North Avenue Beach, a popular spot offering breathtaking views of Lake Michigan and the city skyline.

The vibe at the beach was incredible and lively, especially while passing by the massive volleyball court and the food shacks. We took a long, relaxing walk to the North Avenue Beach Pier, enjoying the fresh breeze and the stunning blue waters of Lake Michigan.

I wish we had some room in our stomachs to try one of the restaurants. But if you do, stop by Shore Club Chicago, a high-end beachside restaurant offering a variety of food and drinks (based on Google reviews) with an amazing view of the lake.

Ulysses S. Grant Monument

As we continued our walk, we reached our next spot, Ulysses S. Grant Monument, a quick photo stop on the way to the boardwalk. The monument is located near the South Pond and is a tribute to the 18th President of the United States and Civil War hero. This beautiful stone entryway features an imposing equestrian statue of Ulysses S. Grant, symbolizing his leadership and military prowess.

Peoples Gas Pavilion

Next, we visited the Peoples Gas Pavilion, a.k.a, the Honeycomb. Designed by award-winning architect Jeanne Gang, famous for Chicago’s Aqua and St. Regis buildings, it features fluid, nature-inspired structures. This design is a favorite among photographers, and I couldn’t resist capturing the picturesque scene, which made a stunning backdrop for our photos.

South Pond and Nature Boardwalk

Our final stop was the South Pond, a tranquil oasis surrounded by dense greenery and walking paths. We walked along the Nature Boardwalk, observing many native plants and birds, and watched a breathtaking sunset.

If you visit this park during the day, visit the charming Café Brauer for a quick refreshment.

Chicago River Cruise

On our second day, we embarked on a Chicago River Boat Cruise, a must-do experience for all. We booked the Architecture Tour by Summer Of George Tours, offering an insight into the city’s iconic architecture.

It was a fun 1-hour tour where we discovered many fascinating insights about Chicago’s history and architecture. It was the perfect way to explore the city, gliding along the Chicago River and enjoying the beautiful blend of historic and modern buildings.

River North District

After a fun boat tour, we headed to the River North District, a vibrant neighborhood known for its arts scene, bustling nightlife, and stylish eateries. Moreover, this neighborhood is also home to several iconic skyscrapers and architectural landmarks like the Wrigley Buidling and Tribune Towers.

Millennium Park

Finally, we headed to the famous Millennium Park, home to the Bean. The park resides in the heart of downtown and features several iconic attractions, from Cloud Gate to Jay Pritzker Pavilion.

Millennium Monument

We started our journey at the Millennium Monument at Wrigley Square, featuring a series of columns and a central sculpture within a water fountain. This grand architectural piece, designed by architect Francis K. McCarthy, pays homage to the city’s history and development.

Cloud Gate

Next, we visited Chicago’s most beloved art installation, “The Bean.” This reflective sculpture by Anish Kapoor offers stunning photo opportunities and a unique reflection of the city’s skyline. Unfortunately, access to the Bean was closed due to ongoing construction work, so we’ll have to save it for our next visit!

Jay Pritzker Pavilion

Lastly, we stopped by the Jay Pritzker Pavilion to attend the Chicago Jazz Festival. We were truly blown away by the grandeur of this outdoor concert venue designed by Frank Gehry. The combination of live jazz and the picturesque setting made for an unforgettable evening.

You can also visit Crown Fountain (designed by Jaume Plensa), an interactive fountain that displays video images of Chicago residents, and the stunning botanical park Lurie Garden.

Other Iconic Attractions We Recommend

Chicago is home to a plethora of world-class museums and parks. Here are some more that we highly recommend visiting if you have more time to explore.

Grant Park

Grant Park is one of the top spots in the city, an urban oasis home to many top attractions of Chigaco. Here are some top attractions that we recommend visiting in Grant Park.

• Clarence F. Buckingham Memorial Fountain – also known as the Buckingham Fountain, is an iconic fountain in the heart of Grant Park. This typically remains open from May to mid-October and offers a stunning light and sound show every evening for its visitors.
• Field Museum – immerse yourself in the interactive exhibits at the world’s one of the best natural history museums, from mummies to the largest Tyrannosaurus rex ever discovered (SUE the T. rex).
• Shedd Aquarium and Adler Planetarium – if you’re traveling with kids, we highly recommend visiting these two fun places. They are both educative and entertaining. One lets you explore the mighty creatures of the sea, while the other opens a portal to our vast universe.

Skydeck Chicago

If you love visiting observation decks, head to Skydeck at Willis Tower (formerly Sears Tower) and enjoy a breathtaking view of Chicago. Located on the 103rd floor, Skydeck offers an immersive museum experience, stunning views, and a thrilling experience to look straight down the glass balcony extending four feet outside the building.

The Art Institute of Chicago

Explore one of the oldest and largest art museums in the United States, housing the world’s second-largest collection of Impressionist and Post-Impressionist art. This museum is huge and would take more than half a day to see all the top exhibits.

Navy Pier

Navy Pier, Chicago’s one of the most iconic landmarks. This place has something for everyone, from fun rides to quirky shops and restaurants. We only saw the pier from our river cruise tour but would have visited if we had more time.

Four Must-do Activities in Chicago

If you have two days or less to explore Chicago, here are four must-do activities to let you experience the city to the fullest. These highlights showcase what makes Chicago unique and offer an insider’s perspective of this vibrant metropolis.

Ride the Chicago “L”

The Chicago “L” is one of the most efficient public transit systems in the USA and is a great way to explore the city on a budget. We used the “L” to travel between River North and the South Loop district, and it was super convenient as almost all the major spots were connected. Moreover, even if you’re not riding, watching these elevated trains pass by is fun and a great place to get some postcard-worthy photos.

Try a Deep-Dish Pizza

No visit to Chicago is complete without indulging in a famous deep-dish pizza. Each slice of this culinary icon comes loaded with a generous amount of cheese, sauce, and veggies (or meat). We recommend Lou Malnati’s Pizzeria, one of the best deep-dish pizzas in Chicago. You can read more about Chicago’s culinary scene in my Chicago Food Guide.

Chicago Food Guide: Budget Eateries, Must-try dishes and more

Visit a Jazz Bar or Blues Club

Another thing Chicago is known for is its legendary music scene. The city’s musical roots date back to the Great Migration era when African Americans brought their music to the North. Therefore, visiting a Jazz Bar or a Blues Club is a must. We recommend heading to Buddy Guy’s Legends or Green Mill for an authentic experience.

Take the River Cruise Tour

As I mentioned earlier, River Cruise is one of the best ways to explore the city. The tour offers a fantastic way to see the city’s architectural marvels from the water and a scoop of Chicago’s history.

What We Ate in Chicago

Food is a big part of the Chicago experience, and we made sure to try a variety of local flavors. Here’s a detailed Chicago Food Guide, where I share a list of restaurants we loved and a few top-rated spots you can try.

We absolutely love Chicago—so much that we even considered moving there, though our hearts remain in Seattle. While the winters can be harsh, timing your visit right reveals a city full of world-class museums, delicious food, and stunning views. Pack your bags and experience all that this amazing city has to offer!

Feel free to reach out with any questions or tips, and happy travels!