“Don’t listen to what they say. Go see.”
Chicago is one of those cities that you have to visit in the summer. I’ve been to Chicago several times before but this time I got to really experience the city in a whole new way. You can see all that Chicago has to offer in just a couple of days. My boyfriend and I spent the weekend here, enjoying some amazing views and some really good food. Keep reading to learn about some of my recommendations and take notes for whenever you visit the big city in the midwest!
Stay
I recommend booking a hotel stay in the downtown area. It’s super convenient to the closest shops, restaurants and attractions. We stayed at the Millennium Knickerbocker Hotel right next door to the Louis Vuitton store. The hotel was not my favorite but was walking distance to a lot of places we visited. It would have been nice to have more space in the hotel room, as it felt small. Try to be mindful when booking as the pictures can sometimes be deceiving of the space you actually get.
Booking information is on their website. Millennium Knickerbocker Chicago
Transportation
For our trip, we chose the cost effective route as Uber and Lyft prices have drastically increased. We were going to be pretty close to everything anyway so we chose to purchase 3-day CTA passes to be able to ride the subway and bus unlimited times the entire trip. These were only $15 a person, an extra $5 if you were purchasing a new card. We were able to take the subway directly from the airport all the way into downtown Chicago. This was super convenient and hassle free. Not to mention, cheap! We were already used to public transit from being out on the east coast, so it wasn’t a big deal to us. Chicago’s subways are MUCH cleaner than New York’s by the way! Of course at night when we went out, we didn’t ride the subway or take public transit because the safety risk. Be sure to keep that in mind.
Another way we got around was with bikes. With Lyft you are able to check out a bike and receive the first 30 minutes free. This is another cheap option but also give you an adventure at the same time.
Food
Of course each city is known for their food and Chicago is no different. We made sure to check out some Chicago favorites and get our thoughts.
Breakfast/Brunch
Batter & Berries: 10/10
Tip: Check in on Yelp to join their waitlist way ahead of time. Their wait is typically a few hours long, so do not be surprised. I promise it is worth waiting!
The Whale Chicago: 9/10
We love a good ambiance! Great drinks. If you’re coming with a large group, they have mimosa towers and mimosa kits! Definitely check them out!
Lunch/Happy Hour
Giordano’s: 10/10
Tip: Do not come if you’re starving — the deep dish takes an hour to make! SO worth it though!
Cerise Rooftop: 10/10 — amazing views!
Currently do not have happy hour deals BUT the drinks and the view are amazing! Be sure to check out their swing for the best photo op.
Overhyped Recommendation: Harold’s Chicken. For me personally, the chicken was not very flavorful. The sauce they have wasn’t that great. I’ve definitely had better chicken. You wouldn’t be missing out if you passed on this one.
Dinner
Nico Osteria: 10/10
To my surprise, my favorite part about this restaurant was their cocktails. I’m not sure who was bartending that night, but they knew what they were doing. Ha! I ordered their popular Rigatoni pasta which did not disappoint. Check them out if you’re in the city.
Things To Do
I’ve included a few free options too!
Catch some amazing views of Chicago’s skyline while also enjoying the sunset.
If you love art and museums, this is a great one to check out!
In the summer, the Navy Pier offers free firework shows weekly.