- May 26, 2021

Travel Beyond Texas – Spend a Weekend in Chicago

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After a year of no travel, taking a weekend away is more welcome than ever. Not that we don’t love spending time in the great state of Texas. We took many day trips and experienced some incredibly unique staycations in the last year – like these glamping excursions. But as Covid restrictions relax, and our vaccination shots set in, planning weekend trips is back on the books.

If you’re ready to travel beyond Texas too, follow along with our adventures here and on our Instagram account. Now, without further adieu…

Here’s how to spend a weekend in Chicago!

Friday –

Once you’ve landed and settled in to the Windy City, head to the West Loop neighborhood. Here you will find the awesomely instagrammable WNDR Museum. Chicago’s first immersive experience, the museum is constantly changing, adding new ways to experience art and technology. It currently includes Chicago’s first-ever Infinity Mirror Room by iconic Japanese artist Yayoi Kusama. But that’s not all! Even the bathroom is an experience at this stimulating and entertaining spot. Pro tip – push the button (even though it says not to).

WNDR Museum
1130 W Monroe Street

Next up, wander over to Madison Street. Though its history is a bit gritty, the street is now home to upscale apartment buildings, restaurants, and plenty of sports bars (it’s also a great place to stop on the way to a Bulls or Blackhawks game). We happened to wander into Black Barrel Tavern and enjoyed the clientele, which included a few four legged friends.

After all that fun, you’re going to need to fuel up for the remainder of the evening. What better food choice for your first night in Chicago than PIZZA?! We could dedicate many a post to the debate about who has the best pizza but we’re not going to go there. Whether you like deep dish, thin crust, or even a style made famous in another city, you’ll find it in every neighborhood. I’ll dare to share my personal favorites though: Pizano’s and Aurelio’s Pizza.

Chicago Pizza

Ready for more picture perfect locales? There’s no shortage of filming locations in and around the city – if you are interested in seeing things like that in real life. Here are a few of our faves. Another thing there seems to be no shortage of is TV show and movie inspired pop-ups.

Check out Replay Chicago and see what they currently have going on. At the time of our visit, the Lincoln Park location was paying homage to “The Office.” Here are a few pictures to give you a better idea of the experience.

Replay Lincoln Park
2833 N. Sheffield

After all that adventure, it’s probably time to call it a night. Located right in the heart of Magnificent Mile, we spent our first night at DoubleTree by Hilton where there’s a full array of amenities including an on-site restaurant, bar, and rooftop pool.

Saturday –

Day one was action packed so yours truly spent the morning sleeping. Had brunch been on the agenda, we would have tried to get a reservation at AO Hawaiian Hideout. The newest and hottest HAWAIIAN-inspired restaurant in Chicago’s South Loop, this hidden tropical gem features a luau brunch with an Elvis tribute band. We’re all shook up just thinking about it!

Photo via AO Hawaiian Hideout on Instagram.

AO Hawaiian Hideout
1315 S. Wabash Avenue

Since you’re already on the South side, try to hit up a White Sox game. If you’re really lucky, you may be in town when they host their annual Elvis night (though it isn’t happening in 2021). If you’d rather see the Cubs play, make your way up to Wrigleyville on the L. There’s plenty to do and see in that area, even if there isn’t a game.

Another option is to head out of the city a bit and check out one of the neighboring communities. Nearby towns we recommend include Evanston, Willamette (home to the only Taj Mahal-style temple in the US), Riverside, and Highland Park. The latter is where you’ll find many John Hughes movie filming locations and was once home to Michael Jordan and currently home to Billy Corgan of the Smashing Pumpkins.

On this most recent trip, we traveled out to Oak Park which is famous as the hometown of Ernest Hemingway. It’s also where Frank Lloyd Wright spent much of his early career. You can wander the neighborhood near his studio to see multiple FLW designed and inspired homes.

Back in the city, you may want to hit another pop-up because, as previously mentioned, there’s no shortage of special exhibits and events in the Windy City. The Friends Experience was definitely a highlight – though sadly it closes May 31. You can also visit the experience in New York and Atlanta. Perhaps other cities will be added soon!

Before heading to dinner and drinks, check out the 21c Museum gallery. 21c Museum offers unprecedented access to the work of some of today’s emerging artists, every day all day. It’s free and open to the public 365 days of the year. And here’s something really cool: you can sleep there! That’s right. We had a legit night at the museum. While the first two floors are filled with modern art, the upper floors contain stylish and comfortable hotel rooms. Learn more about how you can book your stay here.

Since you’re right in the middle of downtown, there’s no shortage of spots to eat and drink. No matter which way you turn, you’ll likely find a fun place to park yourself for the evening. We wandered over to Hubbard Street and found the picture perfect JoJo’s Shake Bar, El Hefe, and O’Callaghan’s Irish Pub.

Sunday –

Before heading to Midway (where you can fly home to Austin direct on Southwest), brunch was most definitely in order. Just around the block from 21C is Goddess and the Baker. Their website states that they are an energetic gathering place with good food, fun treats, and excellent coffee. We can attest to all of that. Try the iced brown sugar cold foam latte. Not only is it tastier than the brown sugar latte at Starbucks, it’s cheaper! They have a multitude of really creative and yummy coffee drinks. Check them out here. The food choices are just as delightful. And make sure you save room for dessert! Their cakes and cookie are to die for. Yes, that’s key lime cake baked into an actual lime!

Well, there you have it. The perfect way to spend three perfect days in Chicago! Of course, if you have more time than what’s outlined, there are many many many more things to do – we didn’t even touch on the more touristy locales like the observation deck at the Willis Tower, Millennium Park, the Field Museum, etc.

Stay tuned for more Travel Beyond Texas trips coming soon! And in the meantime, check out these articles about some of our favorite Texas day trips: