Guide to Long Weekend in Chicago

long weekend in chicago

I love having friends visit, because it gives me a chance to see my city through fresh eyes again and run around town playing tour guide! It’s fun to feel all proud inside, showing off all the places and people that make my city so great.

A couple weeks ago, Eric and I had our very first visitors (aside from family, of course), Chelsea and Ryan, fly in for a few days to check out our new lives in The Windy City. Eric was working the first couple of days they were in town, but since I hadn’t started my job just yet, I got to explore with Chels and Ryan! Once the weekend came, we all had a blast running around and sight seeing together.

By Sunday morning when Chelsea and Ryan left, we had pretty much conquered Chicago and knocked off everything off their list, plus more. They got the perfect mix of tourist and local experiences.

Check out our itinerary for a long weekend in Chicago below!

[Late Night of Arrival – WEDNESDAY]


Chels and Ryan got in pretty late, but we couldn’t let the night completely go to waste! We took them for the their very first Chicago dog at the famous Wieners Circle. Just as a PSA, this place can be pretty crazy…they’ve got a Dick’s Last Resort vibe, but the dogs are delish.

[Day 1 – THURSDAY]

We were so productive today! Chels, Ryan, and I started the day with Pumpkin Spice Lattes (ugh, I know so basic) and made our way downtown to walk around the river bridge area right by the Wrigley Building. You can get some gorgeous backgrounds for photos there.


Next up, we knocked out several top Chicago attractions – the Bean in Millennium Park (aka Cloudgate), Buckingham Fountain, a walk around Soldier Field, and the Shedd Aquarium (perfect for getting out of the rain). We stopped for a quick bite in between all that at The Protein Bar – it reminds me of a lighter Chipotle.

long weekend in chicago

Took this at the Bean with space to photoshop Eric in since he was at work a couple blocks away...

Took this at the Bean with space to photoshop Eric in since he was at work a couple blocks away…



That evening, Eric and I took Chelsea and Ryan to grab some delicious Korean BBQ and sushi at a nearby restaurant called Yuki Hana. This place is also BYOB and you get to cook the BBQ yourself on grills at the table, so it’s a fun place to chat and eat. Afterwards, we went to check out this really cool, slightly hidden, tropical themed bar called Three Dots and a Dash – go!! The drinks come in these awesome glasses and have super interesting flavors. It was the first time for our group, and we loved it.



Chels, Ryan, and I kicked off the day with a trip to Wrigley Field. I would’ve loved to take them to a Cubs game, but the boys were on the road. The forecast showed rain all day, but the weather was cooperating beautifully, so from there we headed downtown and walked around Navy Pier.



While we waited for Eric to get off work for an early deep dish pizza dinner, we walked around Magnificent Mile to shop a bit. Well, by shop I mean load up on gummies at Dylan’s Candy Bar. The four of us had dinner at my favorite Chicago pizzeria Lou Malnati’s, leaving so stuffed and happy as usual.



Next, it was back to the apartment to freshen up for a night out! We went to a bar called Guthrie’s in Wrigleyville that is quickly become one of my favorite spots. They have a whole wall of boardgames you can play while you sip on local brews. We also swung by a second bar called Sheffield’s, and then got a late night heavenly grilled cheese at Cheesie’s not far from home.


All dayyy fun dayyy all together, because Eric was finally off for the week!! The day was off to an early start to beat the crowd at the Willis Tower skydeck. The views were stunning, and the people looked like ants as we looked down through glass from 1,451 feet above the ground. We got there around opening at 9:30 am and highly recommend this – the line was crazy an hour later.


After grabbing a quick lunch at M Burger, we made our way to the river for our architecture boat cruise on Chicago’s First Lady. Our tour guide was the sweetest and it was such an amazing way to see the city! I feel like this is a must do.


That afternoon, we went to watch the Texas Longhorns play at Chicago’s UT bar, Stanley’s.* We munched on quesadillas, queso, and Texas teas – it was all pretty delicious for bar food. Once UT won, we ventured off to the John Hancock Tower’s fancy lounge on the 96th floor – our last stop for Chels and Ryan before they left early the next morning. The drinks are pricy, but it’s worth getting one to get a glimpse of the gorgeous nighttime, panoramic city views.


Our friends had a wonderful time in the city, and Eric and I had such a fun time showing them around! This was the perfect adventure around town that allowed them to get the full Chicago experience, but also was still so much fun for us supposedly now “locals.” I’m looking forward to having more visitors – if you have a favorite for your guests that I missed, I want to hear!


*Note: Stanley’s has sadly been closed since I originally shared this post! Have no fear though, if you are a Longhorn in the city, Old Grounds Social has been declared the new watch party spot.

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