Our First Trip to Chicago: 2 Day Itinerary
Chicago had been on my travel wish list for years, and I finally got the chance to visit on a girls’ trip in early May. We spent two full days exploring the Windy City, and let me tell you, this city got downtown right! It is truly one of the most well designed, clean, and beautiful downtowns I have ever seen.
What stood out to me most was the architecture. Everywhere I looked, there seemed to be another impressive skyscraper or historic building, each with its own unique design. I also loved seeing the colorful tulips blooming along Michigan Avenue and seeing the famous Cloud Gate sculpture, better known as ‘The Bean,’ in person.
If you’re planning your first trip to Chicago, this 2-day itinerary covers many of the city’s most iconic attractions, including Millennium Park, the Chicago Architecture River Cruise, Navy Pier, and Chicago 360.
Quick Overview of our 2 Day Chicago Itinerary
We stayed in the Magnificent Mile area at the Hyatt Centric Chicago Magnificent Mile, which made it easy to walk to many of these attractions and maximize our limited time in the city.
Day 1: Visit Cloud Gate (The Bean) and Millennium Park. Explore Michigan Avenue and the Magnificent Mile, with stops at the Starbucks Reserve Roastery and Giordano’s Pizza. Enjoy sunset views from Chicago 360 observation deck. Explore Devon Avenue in the evening.
Day 2: Take the Chicago Architecture Center River Cruise aboard First Lady. Walk along the Chicago Riverwalk and enjoy rooftop views from LondonHouse Chicago. Explore Navy Pier, ride the Centennial Wheel, and experience Flyover Chicago.
Where we stayed in Chicago
For our first trip to Chicago, I spent quite a bit of time researching where to stay. Since we only had two full days in the city, I wanted a location that would allow us to walk to as many attractions as possible and minimize time spent in traffic or on public transportation.
We ultimately chose the Magnificent Mile area, close to the Chicago River, and I think it was the perfect base for a first-time visit. Many of Chicago’s top attractions, including Millennium Park, the Riverwalk, Michigan Avenue, Chicago 360, and the architecture boat tours, were either within walking distance or just a short Uber ride away.
We stayed at the Hyatt Centric Chicago Magnificent Mile, and I would happily stay here again. The location was excellent, tucked away on a quieter street but still just a few minutes from Michigan Avenue and the river. We walked almost everywhere during our trip, which made sightseeing much more enjoyable.
The hotel itself was modern, comfortable, and well maintained. The rooms were spacious by city standards, and the staff was friendly throughout our stay. There was also a Starbucks in the lobby, which came in handy on busy sightseeing mornings when we wanted a quick coffee before heading out.
For a short first visit to Chicago, I don’t think we could have picked a better location. Staying at the Hyatt Centric Chicago Magnificent Mile made it easy to follow this itinerary with very little commuting, allowing us to spend more time exploring the city and less time getting around.
Day 1: Millennium Park, Michigan Avenue, and Chicago 360
We spent our first full day in Chicago exploring some of the city’s most iconic attractions. The day included Millennium Park, Michigan Avenue, stunning skyline views from Chicago 360, and plenty of time walking around downtown Chicago.
One of my favorite parts of the day was simply experiencing the city’s atmosphere, from the beautiful spring tulips lining Michigan Avenue to the impressive architecture surrounding us at every turn.
We started the morning with breakfast at Sunny Side Up. It was a nice brunch spot in a 3 storied historic building, perfect to fuel up before a busy day of sightseeing.
Cloud Gate and Millennium Park
Our first stop of the day was Cloud Gate, better known as “The Bean” due to its shape that resembles a bean. This iconic stainless steel sculpture has become one of Chicago’s most recognizable landmarks, and I can see why. Seeing the city’s skyline reflected across its curved, glass like surface was fascinating.
As you walk around it, the reflections constantly change, creating different perspectives of the surrounding buildings and people. There were crowds surrounding The Bean, but it is so large that there is plenty of space for everyone to get their perfect pictures. It is completely free to visit and is located right in the heart of downtown Chicago.
After visiting The Bean, we continued exploring Millennium Park. This large downtown park is home to several public art installations, gardens, and event spaces. Even though it was a busy weekend morning, the park never felt overly crowded.
We walked through the park to Buckingham Fountain, although it happened to be closed during our visit.
The Art Institute of Chicago is also located right next to Millennium Park. While we didn’t have time to visit on this trip, it is considered one of the best art museums in the country and would be an easy addition to this itinerary if you have more time in Chicago.
Walk Along Michigan Avenue
After Millennium Park, we continued our sightseeing along Michigan Avenue.
Michigan Avenue is one of Chicago’s main shopping streets. The section known as the “Magnificent Mile” is lined with brand-name stores, luxury boutiques, restaurants, hotels, and some of the city’s most recognizable buildings. While shopping is a big draw here, one of my favorite parts was simply walking around and taking in the atmosphere.
We visited in spring, and the sidewalks were lined with colorful tulips in full bloom. It was a sight to see! Combined with the impressive architecture and bustling city streets, it made for a beautiful walk through downtown Chicago.
One of the things I loved most about Chicago was its architecture. Even when we weren’t visiting a specific attraction, I found myself constantly looking up at the surrounding buildings. The skyscrapers here are impressive, and it felt like there was always another beautiful building around the corner.
Along the way, we stopped for Ghirardelli ice cream. As San Francisco locals, we found it funny that we ended up getting Ghirardelli in Chicago, but it was right there and exactly what we were craving after several hours of walking.
We also stepped inside the Starbucks Reserve Roastery, one of the largest Starbucks locations in the world. The four-story building is impressive, with multiple levels, coffee bars, and dining spaces. However, it was extremely crowded during our visit. The lines to order were long, and finding a place to sit seemed nearly impossible, so we didn’t stay long.
For lunch, we tried Giordano’s, one of Chicago’s most famous deep dish pizza restaurants. They have several locations throughout downtown Chicago, making it an easy stop during your sightseeing. Honestly, deep dish pizza is not my thing. I preferred the thin-crust pizza here, which was very good!
After our hearty pizza meal, we were stuffed and continued walking north along Michigan Avenue all the way to Chicago 360, enjoying the architecture and city views along the way.
Sunset Views from Chicago 360
For sunset, we headed to Chicago 360, one of Chicago’s two major observation decks. The other popular option is Skydeck Chicago at the Willis Tower (formerly known as the Sears Tower). Both offer impressive city views, but we chose Chicago 360 because of its views of Lake Michigan and the additional attractions available here.
➡️I recommend visiting Chicago 360 observation deck during sunset time for daytime and nighttime views
One of the unique experiences at Chicago 360 is TILT, a platform that slowly tilts visitors outward over the edge of the building. We skipped it ourselves, but it looked like a fun option for anyone looking for a more thrilling experience.
I highly recommend booking your tickets online in advance if you plan to visit around sunset. We made our reservation the day before, and many of the sunset time slots were already filling up.
We arrived before sunset and stayed for a couple of hours, which allowed us to experience both the daytime views and the city lights after dark. There is also a bar where you can purchase drinks and snacks while enjoying the views.
From the glass enclosed observation deck, we could see Chicago’s impressive skyline stretching in every direction, along with the blue waters of Lake Michigan. If you only have time for one observation deck during your visit, I think Chicago 360 is an excellent choice.
Dinner on Devon Avenue
We ended the day with dinner on Devon Avenue, one of Chicago’s best known areas for Indian and Pakistani food. This lively stretch is filled with restaurants, grocery stores, sweet shops, and clothing stores.
The restaurant we chose was not good, so I won’t specifically recommend it. We were looking for a restaurant with good vegetarian options and unfortunately, ended up making a poor choice. If you’re looking for popular options, Ghareeb Nawaz, Uru Swati, and Sabri Nihari are all well-known choices in the area. If you’re vegetarian, I would do a bit more research ahead of time than we did.
After dinner, we headed back to our hotel to rest before another full day of exploring Chicago.
Day 2: Architecture Cruise, Riverwalk, and Navy Pier
Our second day in Chicago focused on some of the city’s most famous waterfront attractions. The day included an architecture boat tour, a stroll along the Chicago Riverwalk, and an evening at Navy Pier.
We started the morning with breakfast at a popular bagel shop, Gotham Bagels, near our hotel. It was crowded, but the bagel sandwiches were good. From here we walked down Michigan Ave to the Chicago Riverwalk area for our architecture cruise.
Chicago Architecture River Cruise
While researching popular things to do in Chicago, the architecture cruise was the activity that came up over and over again, and it ended up being one of my favorite experiences of the trip. Well, second only to The Bean.
If you only have time for one tour during your visit, I would strongly consider making it the architecture cruise. We did this on Day 2 of our itinerary because the weather was sunnier than our first day, so I would recommend planning it around the forecast if possible.
We booked this Chicago Architecture Center River Cruise aboard First Lady for 1 PM and arrived about 30 minutes before departure. The boarding line was already quite long, so if you want a railing seat, I would recommend arriving even earlier. Most people headed straight for the open air upper deck, and we did the same.
As we cruised along the Chicago River, we passed dozens of skyscrapers and historic buildings while learning about their design, history, and significance from the tour guide. I was surprised by how informative the narration was and learned a lot about the city that I would have otherwise missed.
One of the things that stood out to me was how impressive Chicago’s skyline looks from the river. We had already admired the buildings while walking around downtown and from Chicago 360 the day before, but seeing them from the water was a completely different experience.
My favorite part was when the boat reached the intersection of the Chicago River and Lake Michigan. From here, you get an incredible view of the entire Chicago skyline, which was easily one of the best views we saw during our trip.
➡️This is the tour I did, and highly recommend – Chicago Architecture Center River Cruise aboard First Lady
Chicago Riverwalk
After the architecture cruise, we spent some time exploring the Chicago Riverwalk. Since we had already seen much of it from the boat, we only walked a portion of the path, but it was still a pleasant place to stroll and enjoy the river views.
The Riverwalk is lined with restaurants, outdoor seating areas, public art, and plenty of spots to sit and watch the boats pass by. We also found several street vendors selling Chicago souvenirs and picked up a few items to take home.
Before heading to Navy Pier, we made a stop at the rooftop terrace at the historic LondonHouse Chicago hotel. The rooftop offers beautiful views of the Chicago River, surrounding skyscrapers, and Lake Michigan in the distance. It was another great spot to admire Chicago’s skyline.
You do not need to purchase a drink to access the outdoor viewing area, although we ended up ordering a couple of drinks and relaxing for a bit.
Navy Pier
We spent the rest of the evening at Navy Pier, one of Chicago’s most popular attractions along Lake Michigan. The pier is home to restaurants, shops, rides, and entertainment, making it a fun place to spend a few hours.
One of the first things that stood out to me was the color of Lake Michigan. The water was a beautiful blue and looked almost like an ocean from certain viewpoints.
While at Navy Pier, we rode the Centennial Wheel for panoramic views of the city skyline and lakefront.
We also experienced Flyover Chicago, which ended up being my favorite attraction at Navy Pier. The immersive ride takes you on a virtual journey over Chicago’s landmarks and neighborhoods, accompanied by special effects that make you feel like you are actually flying through the city.
➡️I highly recommend the Flyover Chicago Experience at Navy Pier
Since we visited Flyover Chicago toward the end of our trip, it felt like a fun recap of many of the places we had already seen. It was a unique experience and a great way to wrap up our Chicago sightseeing.
Before leaving, we spent some time in the food hall area, enjoying coffee, Garrett Popcorn, and a few sweet treats while taking a break from sightseeing.
For dinner, we headed to Mercadito on Kinzie Street. The restaurant was packed with a lively atmosphere. While the food was decent, we found the portions very small for the price.
We then walked back to our hotel, once again appreciating what a great location it was for a first time visit to Chicago.
Final Takeaways
Chicago exceeded my expectations. Between the impressive architecture, beautiful waterfront, walkable downtown, and iconic attractions, it was a city that was easy to enjoy from the moment we arrived.
If you’re visiting Chicago for the first time, this 2 day itinerary covers many of the city’s highlights while still leaving time to simply enjoy being in the city.
