Two weekends ago I got the chance to visit a city that had been on my bucket list for some time; Chicago. I’ve spent so much time traveling outside of the United States that sometimes I feel like I’ve neglected to see all that the US has to offer. There are tons of cities that I’d love to visit within the next few years and Chicago was first on the list. When my fiance’s job took him on a business trip there, I hopped on the chance to make it into a long weekend for us.
I wanted to round up a few of my favorite spots that are perfect if you plan on visiting for a long weekend too–
Where to Eat
Siena Tavern–This trendy Italian spot in River North did not disappoint. The waiter was friendly and helpful with the menu and and knowledgeable about their extensive wine list. The giant meatball appetizer is a must have. For entrees, we went with the bolognese and the kale and sweet potato pizza. Both were delicious and we would recommend them to anyone looking for a solid Italian meal in a less traditional environment. Bonus tip– if you go late, Siena Tavern turns into more of a lounge that still offers late night food (We went around 11pm). Not only do you get a great meal but you ALSO get great music.
Summer House Santa Monica– The name may be deceiving but this restaurant is actually in Lincoln Park not California (a girl can dream though!). The fun summer decor will have you thinking you are relaxing at brunch on the beach. The menu has something for everyone. For those looking to stay healthy they offer omelettes and avocado toast. For those who like it sweet, they offer giant stacks of pancakes and cinnamon buns.
RPM Steak– I had just finished Whole 30 when we went on this trip and was dying for a nice steak dinner where we could really go all out. There are tons of great steakhouses in Chicago, although some are chains and not native to the Chicago area. We decided we wanted to go with a local one that we couldn’t experience anywhere else. After reading countless reviews, we went to RPM steak and I was so glad we did. There are so many dishes here that I recommend trying; the coal roasted king crab being the star appetizer, the cheddar popovers, the filet mignon, and the spicy broccolini. For dessert, I recommend the Baked Alaska or the cookies and cream ice cream sundae.
The Hampton Social– Live music, laid back beach decor, and good drinks. What more could you want in a brunch experience? As a New Yorker, I loved the Hamptons vibes here. My recommendations here are the breakfast sandwich and butternut squash toast.
Pequod’s– Because you NEED to have deep dish pizza. We decided to forego Lou Malanati’s and Giordano’s in lieu of a more local favorite and understated spot. Pro tip– You can actually put in a “table request” weeks before you plan on going. They don’t actually take reservations but this cuts down on the wait time tremendously. Definitely recommend the more touristy spots as well! But if you’re looking something a little more off the beaten path I would go here.
Where to Drink
My favorite bar we visited was a Tiki bar called Three Dots and a Dash. The cocktails were cool and creative. The vibe was super relaxed. It was a nice change from your standard bar.
What to Do
The John Hancock Tower (360 Chicago)– You might wait a little bit here but it is SO worth it. Purchase a ticket that includes an alcoholic beverage and take the elevators to the top of the building. From here, you can experience breathtaking views of Chicago with a glass of wine in hand. You won’t want to miss this.
The Skyjack @ The Sears Tower– This has a similar view of the city minus the alcohol and with a longer wait time. Definitely plan on getting here early if you’re going on the weekend to avoid a 2 hour line.
The Magnificent Mile– The shops on Michigan are a MUST if you love the shop. They have everything and everything. It reminds me of 5th avenue!
Millenium Park– The Bean is just one of those things that you have to see.
Where to Stay
Personally, I loved staying in River North because we were near a ton of great bars and restaurants that were all within walking distance. Both Siena Tavern & RPM Steak were a 2-3 minute walk from The Westin. I love the Westin because you’re always guaranteed cleanliness and good service. Not to mention they have great amenities especially with their Westin Workout program that now provides Peloton bikes!
Where to Workout
There are tons of options for fitness classes in Chicago. If you’re in River North, I recommend Barry’s Bootcamp or Flywheel that are nearby. There are also Pure Barre and Orangetheory Studios in Lincoln Park as well as a ton of options in Gold Coast.