I decided to go to Chicago as a trip for my birthday for a couple of reasons…..One, a restaurant that I have wanted to eat at for about 20 years is there. I’m talking about Alinea, led by Chef Grant Achatz, which has been named the Best Restaurant in the World by Elite Traveler, the Best Restaurant in North America by The World’s 50 Best Restaurants, and the Best Restaurant in the U.S. by Gourmet and Business Insider. It is one of only 14 restaurants in the U.S. to earn three Michelin stars. The second reason was that my brother lives in western Pennsylvania and he was willing to drive to Chicago to meet us. While we didn’t take our kids on this trip, we packed as much eating and sightseeing into our trip as we could — and most of what we did would be perfect for families to do together. Here in 4 parts is a run-down of what activities we did over three days in Chicago. Check back soon to read part 2, part 3, and part 4.
Day One
Our Chicago adventure began in the wee hours of the morning. We ended up having to change our flight and leave a day earlier. That caused us to end up with an overnight flight that landed in Chicago at about 4:30 in the morning on Tuesday. After traveling on Monday and airport layovers, we were exhausted. We hopped into an Uber and watched the city slowly come to life as we made our way downtown to the historic Warwick Allerton, bleary-eyed but excited for the days ahead.
The hotel staff was incredibly accommodating, even at that early hour. They couldn’t check us in yet, but they happily stored our luggage. The friendly lady at the front desk, noticing our tired faces, suggested we head to a couple of nearby spots for coffee and breakfast. She recommended Stan’s Donuts for coffee and Wildberry for a full breakfast. She also recommended that we kill some time by taking the pedestrian tunnel to the nearby riverfront park, which piqued our interest.
It was barely 6 am when we arrived at Stan’s Donuts, but the place was already buzzing with activity. We ordered our coffees and couldn’t resist the pastries. I chose a key lime cronut, while my partner went for a toffee donut. We also grabbed a spinach feta pastry to share. After our impromptu breakfast, we felt pretty full and decided to skip Wildberry. We decided to explore and headed down to the waterfront in search of this mysterious tunnel. Unfortunately, we couldn’t find it, and being too tired to wander too much, we retreated to the hotel, hoping against hope that a room might have opened up.
We found it hard to choose from all these pastries.
To our surprise and delight, when we returned, a different staff member informed us that a room was ready. We gratefully accepted the early check-in and then took a three-hour nap.
Feeling refreshed, we ventured out again, this time in search of Chicago’s famous deep-dish pizza. We ended up at Gino’s East, which was just around the corner from the Warwick Allerton, opting for their pre-made lunch special. We got two personal pizzas — one pepperoni and one sausage, which came with either salad or minestrone soup; definitely a good deal for lunch. The sausage pizza was flavorful, but I found the pepperoni a bit lacking. Still, it was a satisfying introduction to Chicago-style pizza.
Deep dish pizza from Gino’s East.
After lunch, we realized we needed a few essentials and walked to a nearby CVS. As we walked back towards Gino’s, we spotted my brother arriving to meet us. We decided to explore the area together, heading towards the river. Along the way, we stumbled upon a butterfly habitat, on the way to Navy Pier, and we decided to go in. The butterfly house is only open during the summer months, but if you happen to stumble on it like we did, it was an enjoyable way to spend a half hour.
You can pay en extra $1 and get a long Q-tip that you can use to feed the butterflies with.
As we wandered by the river, we saw that a river cruise was just about to get underway so we quickly bought tickets. We always enjoy taking tours of some sort — either a walking tour or a food tour — in new cities that we visit, so I recommend these river tours. There are many to choose from. This one was a general history of Chicago tour while the one we went on the second day is focused on architecture. The header image on this post is our view from the boat.
Book Your Stay in Chicago
For dinner, we opted for something quintessentially Chicago — hot dogs from America’s Dog & Burger at the Navy Pier food court. I have to say that while the dog was very good with the tang of yellow mustard, the crunch of the pickle, the bite of the tomato, and the acid of the sport peppers, the hot dog itself was kind of lost underneath all those flavors! But it lived up to the hype.
The Chicago dog from America’s Dog & Burger at the Navy Pier food court.
We capped off the night at 3 Dots and a Dash, a tiki bar I’d been eager to try. Despite having a reservation for 7 pm, we arrived an hour early and were pleasantly surprised when they could seat us right away. My brother had never been inside a tiki bar, so he was taking in everything to see about the bar’s tropical decor and creative cocktails. He got excited about the rum and wanted to taste some by itself and not in a cocktail, so we asked our waitress about flight options. Even though the menu doesn’t list rum flights, we were able to get a taster flight of three different rums. It was the perfect way to sample their rum menu without overdoing it.
The Pearl Diver and the Coconut Midnight Stinger from 3 Dots and a Dash.