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Hey Chicago! weekend adventure guide

There are a million things to do in Chicago, so here are my recommendations of about 10 millionths of the incredibly fun things to do there. We recently took a super-quick weekend getaway to the windy city and we're still talking about it. It was an absolute blast! If you're heading to Chi-Town anytime soon, here are the adventures that kept us solidly entertained for the approximately 48 hours that we were there.

First things first, thanks Southwest for getting us there safely. We took the Chicago “L” transit, aka the subway, to and from the Chicago Midway International Airport (this is where Southwest flies into). It was extremely convenient and easy to navigate, but I would do some research before you go to make sure you know where to get on and off. We also took it to Wrigleyville on game day and while it was crowded, you were never uncomfortably smashed against a stranger. It was $2.50 per person one-way to the game, so I’d say it’s the cheapest way to get around the city as well.

We stayed at the Wyndham Grand Chicago Riverfront. The location was wonderful, we could walk to bars, restaurants, Millennium Park, etc. and had a perfect view of the Chicago River! It was one of the cheaper rates we found on the river and had everything we needed (aka a place to sleep & shower).

Our first stop after checking in around 10 p.m. was the LondonHouse, a riverfront hotel coincidentally right next door to ours. A lot of people recommended we visit the rooftop bar there, so we did. It was a bit misty that night and the bar was really crowded with no place to sit or really even stand; however, I would recommend it you’re not staying on the river walk. Be prepared to spend like $40 on two drinks.

We had a second dinner that night around midnight at Emerald Loop, a little Irish Pub close to our hotel. If your palate is feeling a breakfast for a midnight dinner flavor, I’d highly recommend the bangers and mash. It’s definitely different than previous bangers and mash dishes that I’ve had, but it was like your grandmother's warm comfort food on a chilly night. Perfection. It consisted of four breakfast-like sausages, baked beans and mashed potatoes (my mouth is watering as I type this).

Saturday was all about the Cubbies! We woke up early, enjoyed mimosas and our room’s river view as we all put our (actually Brett’s) Cubs jerseys on and headed to Wrigleyville. First stop was the batting cages at Sluggers World Class Sports Bar, it’s a bar downstairs with batting cages upstairs. Blue Moon, first… coins to hit, second. It was a blast! To our surprise, there weren’t long lines to get into the cage which was ideal. I’d recommend getting there a couple hours before the game started, like we did. After that we bar hopped, hit some Cubs shops and headed into the game. You have to go to a Cubs game if they’re playing at Wrigley and you’re visiting Chi-town! Y’all, even if you’re not a baseball fan, go to eat the Chicago Dog!!! & sing Go! Cubs! Go! I do not usually like hot dogs, but hot diggity dog… I am a Chicago Dog FAN! I am a believer that a bun can make or break whatever you’re eating and the Chicago Dog bun was a perfect combo of sweet and moist. It was no doubt my favorite meal of the trip. Another favorite part of the trip was, like I mentioned, singing Go! Cubs! Go! after the Cubbies won! (We may or may not have listened to that song numerous times on YouTube after the game.) Moral of the story, Wrigley Field for a Cubs game is a must!

After the game we hung around Wrigleyville for a bit, but it gets even more crowded after the game (well at least after a 1:20 p.m. game). We took the train back near our hotel and had dinner and drinks at Public House, another food stop recommended to us. I’d also recommend it if you’re looking for good food and a fun bar atmosphere!

Sunday Funday! We started our morning with coffee from Intellegensia which was perfectly located in the direction we were headed. (Yes, this was another recommendation and that’s why I’m writing this blog post… so when you go to Chicago you can just look here and be on your way… Ha!) My first ever iced matcha latte with oat milk, again yummy; however, it was not nearly as sweet as your typical flavored iced latte. Intellegensia offers a variety of drinks.

It was then time to find The Bean! In writing this blog post I found out it’s not actually called “The Bean.” The real name of the bean looking architectural structure is “Cloud Gate” … say what? Mind blown. Anyway, we found the bean, took the obligatory photo and explored Millennium Park.

It was time to make our way to our architecture tour! Numerous people had recommended doing this tour and there are a lot of companies that you can go through, we chose the Chicago's Original Architecture Tour on Wendella Boats. Our tour guide was entertaining, there were a variety of adult beverages offered and we got to see and learn about Chicago’s amazing architecture while tootling around all three branches of the Chicago River on a Wendella vessel. I’d highly recommend doing this as well.

After our boat cruise, we were hungry and stumbled upon The Little Beet Table. It was a quaint, industrial-modern restaurant focusing on whole foods and is 100% gluten-free. There were a variety of options to choose from and everything we ordered was 100% delicious, including the gluten-free beer! If you’re near The Little Beet Table (845 N. State Street) I’d recommend grabbing a bite.

Our next stop was the John Hancock Center where we visited The Signature Lounge on the 96th floor. The views were breathtaking; you could see for miles. The specialty cocktails were delicious too; I’d recommend the Rose Sangria cocktail which consisted of Absolut citron, rose wine, Aperol, Strawberry puree, lemon juice, simple syrup and garnished with a strawberry.

The Little Beet Table. Signature Lounge view. Public House grub.

Our time in Chicago was coming to an end, but that was the perfect ending to a fabulous trip. If you’re heading to Chicago anytime soon, I hope these recommendations help! You could also ask anyone else who’s been to Chicago and I’m sure they’ll have 1,000 more suggestions. Lastly, travel with your besties and you’re already guaranteed a fantastic time. We loved you, Chicago!


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