Before autumn fades out for good, I wanted to take the time to recap on my recent trip to Chicago in case anyone was looking for ideas for an upcoming trip! While I’ve passed through the windy city many times throughout my life, this was my first trip (in memory, at least) where Chicago was the main destination. I was so excited! I’ve had a big hunch for a few years now that I would adore this city, and oh man, was I right.
In a nutshell, Chicago has that perfect balance of metropolitan bustle and small town coziness that I love so very much. There’s beautiful architecture, exciting food and drink options, a shockingly cool history and cultural identity, and some of the nicest people ever (midwesterners are the best). The weather was also perfect – we went the first weekend of October so it was sunny but with a perfect fall crisp. It occurred to me more than once during my stay there that if it weren’t for the brutal winters, I’d move there in a heartbeat.
Going with my big sister (& travel soulmate) was crucial. We do trips together really well and tend to create itineraries that include a lot of food & coffee, a ton of walking/biking, some ticketed special/local experiences, and relaxing quality time spent together. We like to steer clear of most tourist traps, keep things pretty frugal, and try to really get the feel of the place. This trip did exactly all those things, so without further adieu…Our Perfect Chicago Itinerary!
We started the day early (like 9:30-ish but we recommend even earlier!) at the Doughnut Vault. I love doughnuts, and saw this spot all over the ‘gram, so I made this one a non-negotiable. The aesthetics were so on point and the doughnuts were good, but we got there too late and the buttermilk old fashioned doughnuts had already sold out. Sad.
Starting here was also ideal because it put us in the heart of downtown Chicago. We took our coffees to go and leisurely walked around the downtown area so that we could admire all the city sights, like the iconic Chicago Theater!
We also picked up our metro passes early in the day. This ended up being completely worth it – the subway and bus system in Chicago is really nice and got us everywhere we needed to go. No Ubers or renting cars required!
Eventually we found our way to Millennium Park and The Bean. Our advice? Go early and go on a weekday. We were there when it was relatively empty, but just an hour later it was completely packed.
Around noon we loaded onto a riverboat for an Architecture Boat Tour. Seeing the city from this perspective, on the river that winds through the middle of it, felt really unique. I learned a few cool facts about different styles of architecture, and my only complaint would be that I had hoped for more trivia about Chicago itself.
By the time the tour was over we were starving, so we headed to Pequod’s Pizza for some Chicago style, deep dish pizza. Then it was off to explore the Lincoln Park area. This was definitely one of my favorite neighborhoods – it was beautiful, quaint, and almost London-esque. Doesn’t this house (below) look just like Hogwarts?!
At around 7:30 we made our way to Second City Chicago for an improv show. Guys, I don’t think I’ve laughed so hard for so long in my entire life. One of my favorite activities of the whole trip and a total must!
To end the night, we stopped at the LondonHouse rooftop bar for a quick drink and some stunning sights of the city at night. Then it was off to bed.
Our airbnb was a beautiful 15 minute walk to Wicker Park, so we headed that way for brunch at Etta. Talk about interior dreams.
Wicker Park turned out to be my favorite area, so we spent a good amount of time exploring. We stopped into several shops, sat and chatted over coffee at Wormhole Coffee, did a lot of great people watching, and loved every second of it. From Wicker Park, we walked all the way over to Logan Square where we tried a few beers from a local brewery and where I picked up a “souvenir” candle from Diptyque.
Around 5 p.m it started to rain, so we caught an early dinner at Beatnik. This was maybe my favorite place we ate the entire trip. The interior was so beautiful! There were plants everywhere, a glass ceiling, lots of middle eastern textures, big golden chandeliers, drippy candles, and fun patterns. The food was also so good.
Since it was still raining and we wanted to give our feet some rest, we headed back to our airbnb to relax and watch a movie together. After refueling, we headed back out to Wicker Park to get drinks at The Up Room cocktail bar, then ended the night at a speakeasy called The Violet Hour. The speakeasy culture of Chicago is really cool, so don’t sleep on it. I wish we could have gone to more!
We started out with another brunch in Wicker Park (can you tell it was our favorite area?) at Café Cancale. Then we headed back into the downtown area to visit the Chicago Cultural Center, which was stunning and so interesting. If you’re too crunched for time to do the Art Institute like we were, this is a great (and free!) alternative.
Our last big activity for the trip was renting a couple of bikes and biking up and down the lakefront of Lake Michigan, past the Navy Pier, and through several parks. I was completely floored by how blue the water was, how the lake looked like an ocean, and how it came right up to the edge of the running path! I saw so many people just jump right in (not wade, jump!), from where we were biking. The weather couldn’t have been better, people were out doing all kinds of activities, and it was altogether just stunning.
We biked all the way up to Weiner’s Circle for a Chicago-style hot dog as our last meal. Then we returned our bikes, picked up our bags, and headed to the airport (which was so easy to get to on the subway!)
That was it! I loved it there so much and can’t wait to go back. There were so many things we just couldn’t get to all in one weekend. Bravo, Chicago, you stole my heart.