My first visit to the windy city was full of deep-dish pizza for every meal, cruising down the Chicago River, visiting The Bean at various times of the day, stepping on glass skydecks overlooking the bustling city below, seeing ancient dinosaur fossils, feeding stingrays, and celebrating huge life milestones for close friends.
Trevor and I flew from SFO → ORD on our way there and then flew out of MDW → SFO, which in my opinion was much less chaotic than the bustling O’Hare airport and was an even closer distance to downtown Chicago. If you are traveling into the O’Hare airport, it has a very memorable exit for travelers with neon lights bouncing off mirrored ceilings. The nonstop flight was a little over 4 hours one way. Our visit was from Thursday, September 4 - Sunday, September 7.
Mode of Transportation
Chicago is a fairly walkable city if you are staying downtown, especially in the very late summer season as the weather was nice enough for us to walk outside. However, we definitely used ride-sharing services for destinations that required 20+ minutes of walking to spare our feet and to make sure we got to see everything on our itinerary, so have both Uber and Lyft downloaded for your convenience. I have heard from many Chicagoans that coming in the later fall and winter season might have been a bit too cold to get to experience everything this beautiful city has to offer. The weather in early September was great, temperatures hovering around 64-68 degrees in the daytime. I recommend packing pants and light sweaters and long sleeves. Make sure to bring a jacket or wind breaker, as the wind did make an appearance!
The Hotel
We stayed at Homewood Suites by Hilton Chicago-Downtown. The location of our hotel was the main reason we picked it, as it’s just around the corner of the iconic Trump Tower, Chicago Tribune, and Riverwalk. I recommend staying here due to the convenience of its location. The hotel was super spacious, as it had a living room, kitchen, and bedroom.
The Itinerary
City Pass
During my trip to Seattle a few years ago, I discovered City Pass, which I can’t recommend enough! City Pass is great for several reasons. It helps build out your itinerary, it allows you to make reservations in advance and skip long lines, and it’s more cost effective if you plan to see multiple sites. We each purchased a City Pass, which kept us very busy during our stay and allowed us the chance to experience the best parts of Chicago.
Lou Malnati’s
We arrived to our hotel at around 8:45pm and then made our way to the famous Lou Malnati’s before they closed for the night. This Chicago pizza joint is known for their deep-dish and buttery, flaky crust. It is loved by both tourists and local Chicagoans! There are multiple locations scattered around Chicago and the one we went to was about half a mile from our hotel in the River North location. After trying other pizzas, their deep-dish was ranked #1 in my book! Deep-dish takes around 30-45 minutes to bake, so plan your dining experience accordingly. Ordering a size small will be plenty for a party of two, given the pizza is so dense it will fill you up quickly. I loved it so much, Trevor surprised me and took me to have one last meal at the Lou Malnati’s located 5 minutes away from the MDW airport. He ordered ahead of time, so we were able to enjoy the pizza instantly and make it to our flight on time (we learned our lesson from our first New York trip together!)
Streeterville
Streeterville is one of Chicago's most luxurious areas, packed with restaurants and famous architectural buildings such as Trump Tower, Chicago Tribune, Wrigley Building, and many others. It provides a beautiful view of the Chicago River and showcases different eras of Chicago architecture - from 1920s classics to cutting-edge modern designs. The area perfectly represents Chicago's architectural evolution and ambition. Be sure to walk by in the day and night time. Each view is beautiful and this area really makes you feel like you’re on the set of Batman and in Gotham City! Many of the film’s scenes and buildings are from this neighborhood.
The Bean
After we finished our delicious dinner and walked through Streeterville, we made our way to see the famous Bean. I had only ever seen photos of The Bean, so I was super excited to see it in person for the first time. I didn’t know this, but it’s actually called Cloud Gate. We arrived at around 11:15pm, and we were surprised to see the park was fenced off and there were no people around. We found an area with an opening, so we made our way inside. However, we were stopped by security who let us know the park is closed to the public starting at 11pm. I was still able to see The Bean in all its glory, with a rare sighting of no people around.
The next morning, we put our name for a table at a breakfast place called Wildberry Pancakes and Cafe, which is conveniently located right across the street from The Bean and Millennium Park. While we waited for our table, we made a day time visit to The Bean. There were hundreds of people swarming the famous mirror-finished sculpture that reflects the Chicago skyline. I really recommend seeing it both in the day and night time, as it’s truly a different experience!
We came back to The Bean once more at night, when the park was still open. The reflection of the city skyscrapers in the dark reflecting off the mirrored bean is a sight that I couldn’t get enough of (clearly - we came here 3 times!)
Millennium Park
This public park is home to The Bean, Millennium Monument, and Crown Fountain and is open daily from 6am - 11pm. They often have concerts in the park and other seasonal events worth checking out.
Wildberry Pancakes and Cafe
After exploring the park and The Bean, our table was ready. This restaurant is perfect for breakfast or brunch. We ordered a stack of the danish blueberry pancakes and also ordered a breakfast combo plate to balance out the sweetness overload. If you love pancakes, this place is for you!
Architecture River Tour
The River Tour was my favorite activity we did! There are typically 75-90 minute cruise options to select from, and these tours run from April through November (weather dependent). There are two different spots to board from; Michigan Avenue Bridge area or Navy Pier. We boarded from the Michigan Avenue Bridge area and it was easy to find our reservation from there. Tickets range in the price of $40-50 per person. The tour is one of the best ways to see Chicago's incredible skyline and learn about its architectural history. Make sure to bring a jacket with you for this activity; it definitely got breezy while out on the water. As we made our way back to the boarding pier, I opened my phone to find a very exciting, life-changing email: I had received a job offer from one of the top AI companies, Anthropic! It was the most memorable place to find out my happy news.
Chicago Skydeck
We took an Uber to the Chicago Skydeck at Willis Tower, formerly known as Sears Tower. It was one of the most thrilling attractions we did! Before you make it to the skydeck, you will get to walk through a museum-like experience that tells you the history of the tower and city. The skydeck is located on the 103rd floor, 1,353 feet above ground. The ticket includes The Ledge experience, glass boxes that extend 4.3 feet from the building. You will have 90 seconds to stand on one of the glass boxes and take all the photos you’d like while doing fun poses.
The skydeck offers stunning views of Chicago, where you can even see four different states: llinois, Indiana, Michigan, and Wisconsin
Riverwalk
Following our skydeck experience, we met up with Trevor’s best friend from college, Mikey, after he finished work. We went to the Riverwalk and explored the lovely waterfront views. The Riverwalk is a beautiful 1.25-mile waterfront path along the Chicago River with plenty of restaurants, bars, boat rentals, public art, and green spaces to enjoy. It was super lively, as many people were out and about on a Friday after work, getting their weekend started. We grabbed small bites and caught up on all things life. For dinner, we got in an Uber and ate at the delicious Italian restaurant called Formentos.
The Field Museum of Natural History
The next morning, we explored The Field Museum, home to Sue the T-Rex! (the dino in this photo is not Sue, you’ll have to see her for yourself ;) We spent about an hour and a half in the museum, but you could definitely spend longer given there are lots of exhibits to see. My favorite parts were seeing the dinosaur fossils and visiting the reptile exhibit. Typically, the museum is open daily from 9am - 5pm and the basic admission fee is around $20-25 for adults.
Mikey & Ally’s Party
Following our museum visit, we went back to our hotel and got ready for Mikey and Ally’s party. We came to Chicago to visit Trevor’s best friend Mikey, his wife Ally, and to meet the cutest newborn baby Cooper. The Julian’s had a beautiful housewarming / welcome baby party this weekend. We were so excited to celebrate their new home and welcome baby Cooper to the world! It was so wonderful catching up with our dear friends and seeing them become parents was a very special and happy moment for us!
Freddy’s
Recommended by Danny and Marissa, we took a Lyft from the Julian’s house to the highly-rated Italian market Freddy’s. We were so sad to arrive and see that they were closed! Google and Apple maps said that they were open though. In the few minutes we stood outside the store, more than six people came by excited to eat, but left with the same sad reaction as us when they saw the closed signs. We will try to eat here again on our next Chicago trip!
Freddy’s is known for authentic Chicago Italian specialties such as their vodka gnocchi, Neapolitan pizza, and chicken limon. Photographed below are what Danny & Marissa ordered when they came here and this is what we would have ordered if they were open! This place is not located downtown, but is perfect if you want to experience authentic Chicago Italian food outside the downtown tourist area.
Giordano’s
Due to the miss on Freddy’s, we went to another top-rated Chicago deep-dish pizza restaurant for dinner. I was wanting to experience another deep-dish and compare between Giordano’s and Lou Malnati’s. My favorite pick goes to Lou Malnati’s due to their buttery crust. The tomato sauce and cheesiness for Giordano’s was delicious though! After dinner, Mikey picked us up and took us to get soft serve ice cream. Then, we went back to the Julian’s house where we created a surprise Lego portrait and hung out into the late night catching up with everyone.
Shedd Aquarium
On our last day in Chicago, we squeezed in a full day of activities before our evening flight and finished up our City Pass activities. Our first stop of the day was the Shedd Aquarium, home to a diverse range of marine life. My favorite part of the aquarium was the stingray feeding experience. For $5, we purchased a cup of anchovies that was cut up into 3 pieces. After washing up for the safety of the stingrays, we dipped our arms into the water to pet the cute rays and fed them straight from our hand! This was a highlight of the trip, as I am obsessed with stingrays and will always cherish this experience.
Halfway through our aquarium visit, we grabbed lunch from the cafeteria and sat on the outdoor terrace, which offered a beautiful view of the city skyline. I got a plain hotdog (because that’s how I like it 😆🌭) and Trevor got the Chicago styled hot dog, wrapped in a poppy seed bun topped off with mustard, chopped white onion, bright green relish, tomato wedges, peppers, and celery salt.
The Art Institute of Chicago
Our next stop was The Art Institute of Chicago, where we saw beautiful contemporary, modern, impressionist, post-impressionist, and ancient art pieces. This is "A Sunday on La Grande Jatte" by Georges Seurat - one of the most famous paintings at the museum and a masterpiece of Post-Impressionism. You could spend hours if you wanted to exploring all of the exhibits, but we did a quick 1 hour tour admiring pieces by Van Gogh, Monet, and Picasso.
Pro-tip, the museum has two deals: a FREE ticket if you present a Bank of America credit card during the first weekend of the month, AND if you purchase your tickets an hour before closing the tickets are all 50% discounted. We qualified for both, so instead of paying $64 ($32 x 2), we ended up paying only $16 (and didn’t have to use up one of our CityPass activities!)
360 Observatory Deck
To end our weekend in Chicago, we went to our final destination at the 360 Observatory Deck, formerly known as the John Hancock Observatory. Located at 875 N. Michigan Avenue on the 94th floor of the John Hancock Center, this is another fantastic sky-high Chicago experience that offers panoramic views of the entire city. We weren’t sure what the main difference between the 360 Deck and the Chicago Skydeck was, but after visiting both I can now share the differences.
The 360 Observatory Deck has the CloudBar, perfect for drinks at sunset. The 360 Observatory also has the TILT experience that you can purchase onsite for $15 -18. This is an additional cost that is not included in general admission tickets. TILT is a 2 minute thrilling experience where enclosed glass boxes actually tilt outward from the building, giving you a downward view of the street 1,030 feet below - similar to Skydeck's ledge but with a tilting motion. My hands got a little bit sweaty while I was looking down from the tilted view! If looking to only visit one or the other, I personally enjoyed the overall experience of the Chicago Skydeck more than the 360 Observatory Deck.
My first visit to Chicago gave us everything we hoped for and more. Watching the city reflect in The Bean during the day and sparkle at night, stepping out onto the Skydeck's glass ledge, and walking through streets that felt straight out of Gotham City made every moment feel cinematic. We stuffed ourselves with incredible deep-dish pizza, had the best time feeding stingrays, and shared in the pure joy of seeing our friends become parents to the cutest baby in town. It's a city that balances big-city thrills with genuine warmth, and we're heading home with full hearts and unforgettable memories.