Here’s How to Spend a Perfect Weekend in Chicago

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After a year without traveling, a weekend is more welcome than ever. Not that we don’t love spending time in the great state of Texas. We have done many day trips and had some incredibly unique stays in the past year- like these glamping trips. But as Covid restrictions relax and our vaccinations begin, weekend getaway planning is back on the books.

When you’re ready to travel beyond Texas, follow our adventures here and on ours Instagram account. Well, without further ado …

How to spend a weekend in Chicago!

Friday –

Once you’ve landed and settled in the Windy City, head to the West Loop neighborhood. This is where you will find the incredibly instagrammable WNDR Museum. The museum is Chicago’s first immersive experience. It’s constantly changing, offering new ways to experience art and technology. It currently includes Chicago’s first Infinity Mirror Room designed by legendary Japanese artist Yayoi Kusama. But that’s not all! Even the bathroom is an experience in this stimulating and fun place. Pro tip – push the button (although it’s not called).

WNDR Museum
1130 W Monroe Street

Next, walk to Madison Street. Though history is a little 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 your way to a game of Bulls or Blackhawks). We wandered into the Black Barrel Tavern by chance and enjoyed the clientele that included a couple of four-legged friends.

After all the fun, you need to refuel for the rest of the evening. What better variety of food for your first night in Chicago than PIZZA ?! We could devote quite a bit to the debate about who has the best pizza, but we are not going to go there. Whether you like a deep dish, a thin crust, or even a style that became famous in another city, you will find it in any neighborhood. However, I will dare to share my personal favorites: Pizano’s and Aurelio’s pizza.

Chicago pizza

Ready for more perfect places? There’s no shortage of filming locations in and around the city – if you’re interested in seeing things like this in real life. Here are some of our favorites. Another thing that doesn’t seem to be lacking is pop-ups that are inspired by TV shows and movies.

Check out Replay Chicago and see what’s going on right now. At the time of our visit, the Lincoln Park location was a tribute to “The Office”. Here are some pictures to give you a better idea of ​​the experience.

Repeat Lincoln Park
2833 N. Sheffield

After all this adventure, it’s probably time to call it a night. The hotel is right in the heart of the Magnificent Mile and we spent our first night in DoubleTree by Hilton You’ll find a variety of amenities here, including a restaurant, bar, and rooftop pool.

Saturday –

The first day was full of action so you really spent the morning sleeping. Had brunch been the order of the day, 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 are all shaken just thinking about it!

Photo via AO Hawaiian Hideout on Instagram.

AO Hawaiian hideout
1315 S. Wabash Avenue

Try starting a White Sox game since you are already on the south side. If you’re really lucky, you might be in town for their annual Elvis Night (though it doesn’t happen in 2021). If you’d rather see the cubs play, make your way to Wrigleyville on the L. There is plenty to do and see in this area, even when there is no game.

Another option is to leave the city a little and visit 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. In the latter you’ll find plenty of filming locations for John Hughes films that once featured Michael Jordan and now Billy Corgan of the Smashing Pumpkins.

On this final trip, we traveled to Oak Park, known as the hometown of Ernest Hemingway. Frank Lloyd Wright also spent much of his early career here. You can wander the neighborhood near his studio to see several FLW designed and inspired homes.

Back in town, you might want to pull up a different popup as, as mentioned, the Windy City has no shortage of special exhibitions and events. The friend’s experience was definitely a highlight – although unfortunately it ends on May 31st. You can also visit the New York and Atlanta experience. Maybe other cities will be added soon!

Before heading out for dinner and drinks, visit the 21c Museum’s gallery. The 21c Museum offers unparalleled access to the works of some of today’s emerging artists all day long. It’s free and open to the public 365 days a year. And here’s something really cool: you can sleep there! That’s true. We had a real night at the museum. While the first two floors are equipped with modern art, stylish and comfortable hotel rooms are located on the upper floors. Find out more about how to book your stay here.

Since you are in the middle of the city center, there is no shortage of places to eat and drink. Whichever direction you turn, you will likely find a fun place to park for the evening. We went to Hubbard Street and found the perfect JoJo’s Shake Bar, El Hefe and O’Callaghans Irish Pub.

Sunday –

Before heading to Midway (where you can fly straight to Austin in the southwest) the brunch was definitely ok. Just around the block from 21C is Goddess and the Baker. Their website states that they are an energetic hangout with great food, fun treats, and excellent coffee. We can confirm all of this. Try the frozen brown sugar with cold foam latte. Not only is it tastier than Starbucks’ brown sugar latte, it’s cheaper too! They have a wide variety of really creative and delicious coffee drinks. Look at her Here. The choice of food is just as lovely. And make sure you save space for dessert! Your cakes and cookies are to die for. Yes, this is Key Lime Cake that is baked into a real lime!

Well there you have it. The perfect way to spend three perfect days in Chicago! Of course, if you have more time than described there is a lot more to do – we haven’t even touched the more touristy spots like the observation deck at Willis Tower, Millennium Park, Field Museum, etc.

More trips from Travel Beyond Texas will follow soon! In the meantime, check out these articles on some of our favorite Texas day trips:

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