Now that summer is officially over and the weather is starting to turn cooler, I’ve been reflecting on my hobbies from this summer. Without a doubt traveling was my top hobby. The summer months lend themselves to exploring new places with better weather and opportunities to be out and about. Luckily all of my friends are spread across the country, so I was not short of places to visit. I spent almost every weekend visiting a different city.
Below I’ve rounded up my itinerary from my summer weekend in Chicago with my college roommates! If you’re looking for a casual go-with-the-flow weekend then this plan would be great considering we only made one reservation all weekend.
Friday
- Arrive to town – *Tip* – If you’re coming into O’Hare around rush hour like we did, make sure you look into taking the train into the city. Traffic can get crayzee long and the train takes about 45 minutes into the Loop from the airport (and I swear it’s super easy to figure out even if you’re a stranger to public transportation).
- Walk around Millennium Park – Visit the infamous Bean, and be sure to walk through the entire park to see Lurie Garden.
- Drinks at Cynthia’s – After a walk through the park, we went up to Cynthia’s rooftop bar overlooking Millenium Park. The bar had great drinks with a view and was perfect for a summer evening! You can also have dinner at this spot but will need a reservation if you want to get more than drinks at the bar.
- Dinner on the riverwalk – We wanted a casual dinner on night one, so we headed to the Chicago Riverwalk (type it into your Apple maps and head down the steps once you get there). There are many restaurants and breweries along the riverwalk. We landed at Beat Kitchen Cantina for late night tacos.
- Drinks at Londonhouse – If you’re looking for a rooftop bar in the city with a club vibe, head up to Londonhouse for a very Instagrammable vibe.
Saturday
- Brunch at Hampton Social – Home of the Rose all day signage you’ve likely seen all over Instagram (plus some good brunch food).
- Walk Michigan Ave – After brunch we walked in and out of shops along Michigan Avenue until we reached the Drake Hotel. If you’ve never heard of Michigan Avenue – just know that it is famous for spectacular (and mostly out of my budget) shopping.
- Walk or bike the Lakefront Trail – A great afternoon activity on a summer day in Chicago is visiting the Lakefront Trail. You can rent bikes, walk the trail or sit along the lake and watch everyone else like we did. The trail goes north for about 18 miles.
- Walk Navy Pier, go in the ferris wheel – Another must in Chi-Town is to pay a visit to the Navy Pier. I know that this is the biggest tourist trap in the city, however the view of the city is worth it.
- The best photo opportunity – Milton Lee Olive Park. This spot is right near Navy Pier and has a great view!
- Portillo’s for late lunch – After walking the city, we worked up an appetite and headed to Portillo’s. Every time I’m in the city I must go to Portillo’s. Of course you’re obligated to get a Chicago style dog, but I really come here for the chocolate cake. You know the cake is a must when I don’t ever eat chocolate cake unless I’m at Portillo’s.
- Improv show – In the evening we wanted to switch it up, so we booked tickets to an improv show. I had no idea what to expect since this didn’t fit our standard quo of eating and drinking all weekend, and we all ended up loving this! If you’re also looking for a different activity, I recommend Baby Wants Candy (or probably any show) at Second City.
Sunday
- Beach – After all of our weekend activities, we decided some beach time was needed before leaving town. Since Sunday was our departure day, we stayed close and hung out on Ohio Beach to kill some time.
- Afternoon tea at Palm Court at the Drake – For some reason having tea at the Drake has been on my bucket list ever since I started visiting Chicago as a kid. This is only strange since I don’t even like tea. Shout out to my friends for indulging me and agreeing to go to a $67 per person tea time. You will need a reservation for this. I am so so glad we did this, and I can say I even liked the tea! And in the end, my friends agreed that this was worth the price since you get so much food that you leave stuffed.
I hope you found this itinerary helpful if you’re looking for a casual weekend in the city. If you’re looking for additional activities, I’ve listed some great options below that I’ve done on other trips to Chicago. There’s only so many hours in one weekend!
Other Activities
- Brunch at the John Hancock
- Giordano’s
- Museums
- Architecture tour
- Restoration Hardware
- Wrigleyville – Cubs game
- Lincoln Park Zoo – great in the winter time to see Christmas lights
- Grant Park
- Willis Tower Skydeck
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