88 Hour Trip from BK to Chicago and Back
Dates: April 6-9, 2026 Location: Chicago, Illinois
The Pivot: From Mexico to the Windy City
Due to last-minute changes, we cancelled our trip to Playa Del Carmen, a place that we truly love visiting and had last visited before the COVID shutdown. Instead, we decided to make a last-minute trip to Chicago. For this trip, we challenged ourselves to pack all our clothes into 4 backpacks—no rollers and nothing to check in.
The Packing Strategy: To make this work, we used compression cubes, which greatly aided in saving space. We also had to change our mindset of having a new outfit for each day, which meant wearing some of our clothes for two days.
The Essentials: We of course brought our Yoyo stroller and the Wayb Pico car seat, which was great for the car rides to and from LGA.
We booked our flight with Spirit using our existing credit and took advantage of the Chase Sapphire points we had to book our stay at the Intercontinental and our City Pass to attend the museums. If you are a cardholder, take advantage of the 1.5x points redemption and the $250 credit back with certain hotels—Sara’s suggestion to use enough points to hit that balance saved us big.
Packing light for Chicago, no rollers and just backpacks this time…
Day 1: Deep Dish and Dinosaurs
The 6:30 am departure from LGA was early, but the flight was uneventful. We arrived at our hotel and Cameron was very happy to see the big tulips out front. By 11 am, we were across the street at Lou Malnati’s for our first real taste of Chicago history.
The Order: We went with "The Malnati Chicago Classic." * The Experience: Coming from Brooklyn, the difference is night and day. Unlike the thin, foldable NY slices we’re used to, this is a masterpiece of engineering. It features their legendary Buttercrust—which is more like a savory, flaky pie crust than bread—topped with a massive, edge-to-edge "patty" of lean sausage, extra cheese, and vine-ripened tomato sauce. It’s a fork-and-knife affair that felt like a proper welcome to the city.
We walked over to Millennium Park for "The Bean" and the playground Maggie Daley Park—highly recommended for the slides and swings—before heading to the Field Museum. The big highlight was Sue, the T-Rex, the most complete T-Rex in the country. We ended the day with takeout back at the hotel.
Deep dish from Lou Malnati’s-1120 N State St, Chicago, IL 60610-order as soon as possible when you arrive as it takes 35 mins to prepare
At the “Bean”, a quick 20 min walk from our hotel
At Maggie Daley Park…so much fun, for both girls
Day 2: Double-Deckers and Science Marvels
We started Day 2 at Wildberry Pancakes and Cafe. The service was fast and the food was excellent.
The Order: Go with the Two Eggs Any Style with sausage links or patties. It's served with hash browns, and you can sub your toast for a side of Specialty Pancakes for only $3.
For our big outing, we took the Metra—double-decker trains—to the Museum of Science and Industry. It was a quick 35-minute ride. This was one of the best museums I have ever been to; the sheer scale of the building is breathtaking. Highlights included the U-505 Submarine, the Plane Exhibit, and the "Wicked" exhibit.
For dinner, we headed to The Shops at North Bridge (the Nordstrom mall) right across from our hotel. Cameron was super excited to visit the Jellycat pop-up there, but we found it a bit underwhelming compared to others we've visited. It basically had everything you can already order online—nothing exclusive or location-specific like the unique sets you find at the NYC or London shops. We ended the night with authentic dogs from Chicago's Dog House (located on the 4th floor), Panda Express for the girls, and a fresh fruit platter from Whole Foods.
Candace at Science Museum at Uboat exhibit
Wildberry pancakes across from Millenium Park-130 E Randolph St, Chicago, IL 60601
Day 3: Caffeine, Creatures, and a Goat
We visited the Starbucks Reserve Roastery on Michigan Ave—one of the biggest in the world. Sara had the Smoked Cold Brew, a unique non-alcoholic coffee whisky drink. The girls loved exploring the five floors.
Afterward, a short bus ride took us to Lincoln Park Zoo, which is free year-round. The last time Sara and I were here was 14 years ago! We grabbed lunch at the Park Place Café; I highly recommend the Tropical Grilled Chicken Sandwich with pineapple salsa.
Before dinner, we let the girls enjoy the hotel pool. Dinner was at Girl & the Goat, where we enjoyed a tapas-style feast: Kohlrabi Salad, Goat Liver Mousse, Chickpea Fritters, Wood Fired Chicken, Curry Fried Pork Belly, and my favorite, the Roasted Pig Face. We ended the night with a stroll along the Riverwalk.
At Starbucks roastery, recommend trying the Starbucks Reserve Whiskey Barrel-Aged Cold Brew
A fun filled day at Lincoln Park zoo -2001 N. Clark St., Chicago, IL 60614
Goat liver mousse at Girl and the Goat - 809 W Randolph St, Chicago, IL 60607- Cameron tried it for the first time and really enjoyed it!
Day 4: Aquariums, Ramen, and Airport Tortas
For our last day, we checked out and stored our bags with the bellhop at the hotel. We had breakfast at Beatrix on Streeterville (671 N St Clair St, Chicago, IL 60611). Cameron and Sara loved the Lemon Fluffy Pancakes, while I ordered the Breakfast Burrito, which is packed with scrambled eggs, cheddar, bacon, and finished with a zesty salsa verde.
Next, we hit the Shedd Aquarium. We visited the Wild Reef first for the sharks and rays, then caught a training session. The dolphin show was the main event, though we found the aquariums in Baltimore and Mystic, CT a bit more impressive.
For lunch, we got our ramen fix at Misoya (Mikami). I ordered the Paitan Ramen, a creamy chicken-based broth that reminded me of Tokyo. Cameron had the Tonkotsu, and Sara had the vegetable ramen.
We caught the Blue Line to O'Hare at 4 pm—watching the highway traffic from the train confirmed it was the right choice. Before our flight, we stopped at Tortas Frontera in Terminal 5. Sara had the Chipotle Chicken Torta and I had the Chicken Milanesa. The girls shared a Chicken Quesadilla.
After a short flight, we landed back in NYC and took a quick Uber back to Brooklyn. We have three days of spring break left—and a mountain of laundry to do!
Lemon fluffy pancakes from Beatrix-671 N St Clair St, Chicago, IL 60611
Shedd Aquarium -1200 S DuSable Lake Shore Dr, Chicago, IL 60605
Paitan -chicken based broth ramen from Mikami - 1400 S Michigan Ave, Chicago, IL 60605
James’s Perspective
"Managing a family of four with just backpacks and compression cubes was a challenge, but the mobility was worth wearing our clothes twice! From the buttery crunch of the Malnati Classic to the convenience of the mall right across the street, Chicago delivered. It was great to revisit the spots Sara and I loved 14 years ago while making new memories with the girls."
Cameron’s Corner
"The double-decker train was cool, and my backpacks were heavy but the compression cubes made them fit! I was so excited for the Jellycat pop-up, but they didn't have any Chicago-only toys like the ones in New York. The Chicago pizza is like a giant cake made of cheese and sausage—I liked it way more than regular pizza!"
