I spent 5 days in Chicago, Illinois last week, & I’m already looking forward to going back! Since it’s a 4+ hour flight from San Francisco, California to Chicago, Illinois, I did my best to pack as much as possible into 3 days, & I definitely succeeded! I managed to do everything that I wanted to do & more. That said, here’s my 3 Day Chicago itinerary!
Day 1: Millenium Park, Brunch at Cindy’s Rooftop, & Lincoln Park
Despite the 2-hour time difference, I was up bright & early for my first day of exploring. I stayed at Claridge House, which was only a 2-minute walk from the Clark & Division Red Line stop. Before arriving in Chicago, I met a very kind lady at the San Francisco airport, who recommended using the “L” train, and reassured me that it was very efficient and so much cheaper than San Francisco’s BART (Bay Area Rapid Transit) train. I ended up buying a 7-Day CTA pass for unlimited rides, & I’m so glad I did!
Like any Chicago tourist, our first stop was Millenium Park to see Cloud Gate “The Bean”. We got there early in the morning to ensure there were fewer people around to get the best pictures. We then spent the next hour wandering around the park to see the Millenium Monument, Lurie Garden, Crown Fountain, & Jay Pritzker Pavillion.
After exploring Millenium Park, we went to Cindy’s Rooftop for brunch! Cindy’s has not only a delicious menu but also amazing rooftop views overlooking the park. As I’ve mentioned, brunch is my favorite meal of the day. I also love having brunch as a way to save money while I’m traveling, so that I only have to pay for 2 meals for the day rather than 3.
After brunch, we headed back to the hotel for a quick rest. Then, we walked over to Lincoln Park. Claridge House is only a 14-minute walk from Lincoln Park, & it’s such a cute neighborhood. Most of the houses I walked past were fully decorated for Halloween. At Lincoln Park, I saw animals at the FREE Lincoln Park Zoo, flowers at the Lincoln Park Conservatory, the Lincoln Monument, the Alfred Caldwell Lily Pool, & so much more.
That evening, we had dinner with my sister’s co-worker at GEMINI. I had water & the San Pancho cocktail to drink. Then, my sister & I shared a Baby Wedge Salad, Steak Frites, & a Pineapple Upside Down Cake for dessert. We were so hungry after exploring all day that this was the only meal I didn’t manage to photograph. lol
Day 2: Shopping, Brunch at Little Goat Diner, Skydeck Chicago, Three Dots & a Dash, & Blackhawks Hockey Game
On day 2, I took the train to do some shopping. I’m a huge Kristin Cavallari fan, so I had to stop by her Chicago Uncommon James location. I bought a Cross Ring & Strawberry Fields Earrings.
After shopping, we had brunch at Little Goat Diner. I had coffee & a Kimchi Spiced Boody Mary. Then, my sister & I shared the Smoked Corned Beef Hash with Eggs, a single Apple Cinnamon Pancake, & a fruit cup. The food was delicious, & our waitress was an awesome Chicago native who gave us the inside scoop on what else to do/see/eat during our trip.
After brunch, we hopped back onto the L to Skydeck Chicago. The interactive experience brought you through several rooms with information about famous Chicago landmarks & history. Then, we headed up to the 103rd floor to take pictures in the beautiful glass Skydeck above the city. Afterward, we hopped back onto the L back to our hotel to rest a bit.
Next, we went to the cutest speakeasy tiki bar, Three Dots & a Dash. First off, let me say that my two favorite types of bars are tiki & speakeasy. (The only other bar I’ve been to that was also both was False Idol in San Diego, which I highly recommend too.) I had delicious crab rangoons & two cocktails, Painkiller & Aloha Felicia #4.
After the quick Happy Hour, I headed to the United Center for a Blackhawks hockey game! I’m not a big hockey fan, but I’m a HUGE live sports fan. I honestly wanted to catch a Cubs game at Wrigley Field & possibly get a tour of the stadium. Regardless, it was still so much fun to cheer on the Blackhawks. Plus, tickets were also only $27! After the game, we took the L back to our hotel & called it a night.
Day 3: Chicago Architecture River Tour, Chicago Riverwalk, the Magnificent Mile, Portillo’s, Jojo’s Shake Bar, & Bulls Basketball Game
On day 3, we did a Chicago Architecture River Tour, & this was actually my favorite activity. When I travel I love learning about the local architecture in addition to the history, so this tour was the perfect combination of both. (My Dad is a Civil Engineer, so I’ve always had an innate love of architecture, which is also why I love Europe. So much architecture & history!)
After the tour, I walked along the Chicago Riverwalk & the Magnificent Mile. We then headed to Portillo’s for lunch. I had a classic Chicago Style Hot Dog. (No ketchup!) Then, my sister & I shared fries & onion rings.
After lunch, I went back to the hotel to rest. Then, for Happy Hour, I went to Jojo’s Shake Bar! I had a Witch’s Brew cocktail, a loaded grilled cheese, & shared a Pumpkin Patch Shake for dessert!
After Happy Hour, I went to opening night for the Chicago Bulls at the United Center! I even got a free T-Shirt! I’m a huge basketball fan by the way. My team is and will always be the Golden State Warriors, but who doesn’t love the Bulls right?! I love Michael Jordan, Scottie Pippen, Dennis Rodman, & I was obsessed with watching The Last Dance docuseries.
After the game, we hopped back onto the L to our hotel to start packing up for our last half day in Chicago. It was a lot packed into 3 days, & even though I still wasn’t able to check out Navy Pier or see the Cubs, I look forward to coming back to Chicago again! I hope my itinerary helps you plan out your own. Safe travels!