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The Best Things To Do in Chicago on Your First Visit

by Caitlin
Best Things to Do in Chicago

What to Know When Visiting Chicago for the First Time

From one first-timer, to another first-timer, here’s what to know about traveling to Chicago.

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Weather in Chicago 

Stuff to do in Chicago

Oh man, the weather in Chicago sure is something else. If you like the cold and the wind, you’ll LOVE it here. If you don’t like the cold, well you better bundle your butt! (Yes, even in the summer…) 

If you’re wondering when the best time to visit Chicago is… Well, unless you want to see heaps and heaps of snow,  you are best off visiting in the summer months. For more information about Chicago’s typical weather, by month, check out this site.

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How to Get Around Chicago 

Weather in Chicago

Chicago has a fabulous public transportation system! I found it was extremely easy to get around by the Metro in Chicago. We paid $25 for an unlimited 3-day pass. Which is very reasonably priced! The metro runs frequently and goes all over,  including to the airport!!

One downside is there is no official app, so you better be good at reading maps. However, Google Maps has been stepping up their game when it comes to generating directions for travel by public transportation.

Additionally, we did not have a good time ordering Ubers and Lyfts. It seemed that it took them a long time to get to us, and most of the time we were dropped. I don’t know,  I think there was some missing communication about the pickup spots between the app, the drive, and I.

Pro Tip: Take a water taxi when you go to or leave Museum Island! There are water taxis that run all day from Museum Island to the Navy Pier. Tickets are $10 for adults, one way. You’ll get amazing views of the skyline from the lake.

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Where to Stay in Chicago

Hotels in Chicago

We stayed at TheWIT, right in the heart of Downtown in the Theater District. I love staying at Hilton Hotels, and this one had such a great location. With the Hilton app you can pick your room before check in. I was lucky to get a room on the 22nd floor. We had amazing views of all the beautiful skyscrapers that Chicago is known for.

Best Stuff to do in Chicago

Here are some of the other hotels I was eyeing for our Chicago trip:

By the way, if you’re not looking at staying in Downtown, you might want to check out these other great Chicago neighborhoods:

  • Bridgeport is the home neighborhood of the Chicago White Sox and also has an up-and-coming arts scene packed with globally-inspired restaurants and local dives.
  • The Loop (North or South) is the heart of Chicago and features many of the city’s top attractions and tallest skyscrapers.
  • Pilsen is a richly Latino neighborhood in Chicago and is sometimes known as the heart of the city’s Art District.
  • River North is a former manufacturing and warehouse district, but these days it is full of high-end stores and eateries.
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The Best Things To Do in Chicago

Visit Cloud Gate in Millennium Park Campus (or One of the Many Other Parks in Chicago)

Things to Do in Chicago

Chicago has so many beautiful parks, but you can’t miss a stop at (pictured above) Cloud Gate– aka THE BEAN, in downtown Chicago’s Millennium Park Campus. There is also The Honey Comb up in Lincoln Park, which is another iconic Chicago landmark. Or if you have more time, head down south to visit the Japanese Gardens in Hyde Park.

Check Out the Local Drag Scene

Chicago’s neighborhood Boystown is one of the oldest officially recognized gay neighborhoods in the United States. It’s here that you can shop cool vintage stores, eat at funky and bustling eateries, or hit the town for nightlife that features drag shows, karaoke, and plenty of LGBTQ-friendly dive bars. Another thing to do in Boystown is walk the Legacy Walk, an outdoor LGBTQ history exhibit that colorfully honors heroes and historical events that have shaped the LGBTQ community.

Take an Architecture Boat Tour of Chicago’s Skyline

Boat Tours in Chicago

One of the top recommended things to do in Chicago was a boat tour., But not any boat tour, what was most recommended was an architectural boat tour. Boy, did it deliver. This was one of the best experiences on our first trip to Chicago. It was such a fun way to get to learn more about this beautiful city we were visiting.

We used a company called Chicago River Boat Architecture Tours, and had a great experience! You can book your own tour on their website here.

If You’re Not Afraid of Heights, Visit the Skydeck

Ascend to the very tippy-top of Chicago and see it all from the Floor 103 at the former Sears Tower. There are clear observation boxes that EXTEND out from the building. As someone petrified of heights, I’m happy to staying on the ground and checking out the views via other people’s photos! Buy tickets here.

Watch Some Sports!

Things to Do in Chicago

Chicago is home to so many classic professional sports teams such as the Bears, Cubs, and the Bulls (Oh My!). As someone who comes from a state with ZERO major league teams (hey Virginia!), I knew I could not miss out on the opportunity to catch a game. It was baseball season during my visit, so we got tickets for a game at Wrigley Field (pictured above). And it was iconic.

Whatever sport is in season (football, basketball, or baseball) it is definitely a must to check out a game!

Get Your Education on at Museum Campus

Chicago Museums

Speaking of sports, spending time at Museum Campus is a fun thing to do in Chicago on your first visit. Museum Campus is a 57-acre park in Chicago, right along Lake Michigan, and it’s home to some of the city’s best attractions. Here you can visit Alder Planetarium (America’s first planetarium), Shedd Aquarium, Field Museum of Natural History, and Solider Field (home to the Chicago Bears.).

Pro Tip: Take a $10 water taxi from Navy Pier to right in front of Field Museum, you can also take it from Museum Campus to Navy Pier. You’ll get a stunning view of Chicago’s skyline as you coast across Lake Michigan.

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Where (and WHAT) to Eat in Chicago, Il

Chicago is such an iconic city. I know, you’re probably like, “I sure wish she’d shut up with that word!”. But seriously, from architecture to culture, to sports to food, this city is known for so many things.

And would you look at that! We’ve made it my favorite part of visiting a new city: FOOD. Below, you’ll find explanations on Chicago’s most iconic dishes, plus the top spots to find them.

Deep Dish Pizza

Best Chicago Foods

Now, Chicago-style pizza might not look anything you’re used. Many people say it’s more like lasagna than pizza, but I digress. The ‘za is baked in a pan that has high edges, which gives it a characteristic high edge. This high edge allows for heaps and heaps of cheese and chunky tomato sauce to be piled on top.

Here are some of the best places to try Chicago-style pizza:

Chicago-Style Hot Dogs

Best Chicago Foods

Many cities have their own take on the classic American hot dog, but I really don’t think anyone is doing it like Chicago. The history of the hot dog craze in Chicago is thanks to a wave of Jewish immigrants who realized that American’s love for the little weenies made hot dog vending a great way to earn a living. The classic Chicago hot dog goes as follows:

  • Poppy seed bun
  • All-beef frankfurter
  • Yellow mustard
  • Green relish
  • Hot peppers
  • Red tomato slices
  • Diced sweet onions
  • Pickle spear
  • And finally, a dash of celery salt!

Chicago Italian Beef Sandwiches

Best Chicago Foods

Chicago’s Italian beef sandwich was born in the kitchens of immigrants who were wanting to stretch their meat portions as far they could. This sandwich features thin slices of roast beef served on a long French Roll with au jus (on the side, or as I recommend, DIPPED). You can also get it with either spicy or sweet peppers.

From the recommendations I received, the best place to grab an Italian beef sando in Chicago is Al’s Beef or Portillo’s Hot Dogs. Both have multiple locations around town. Don’t take my word for it, there are dozens of places to get this simple but delectable sandwich and I don’t want to ruffle the feathers of any locals who feel more passionate about this recommendation!

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Where to Drink in Chicago

Breweries in Chicago

Half Acre Brewery + Keeping Together Beers (pictured above) is a Chicago brewery with two locations. They feature a large dog-friendly patio, a small menu of food, and Keeping Together beer from Jester King’s former head brewer Averie Swanson.

The Signature Lounge on the 96th floor (along with dining at The Signature Room on the 95th floor) in the John Hancock Tower is one of Chicago’s many rooftop bars. For a swanky night out, make sure to book a reservation here.

Best Chicago Foods

Billy Goat Tavern (pictured above) is now a chain, but we visited the original “World Famous” tavern and grill in Downtown. The tavern became famous outside of Chicago thanks to Saturday Night Live’s Cheezborger sketch– which is a frigging classic sketch. The tavern has been popular for Chicago way before that. In fact, the tavern’s Wiki page is quite the fun rabbit hole to read. This is a great late night place for some greasy food and cold cheap beer.

Where to Eat in Chicago

Uncommon Ground (pictured above) is a restaurant and brewery in the Wrigley neighborhood. They frequently have live music to pair with their menu. More importantly, they are home to Greenstar Brewery, the first certified organic brewery in Illinois. Along with Greenstar, Uncommon Ground is the first certified organic rooftop farm in the US! There are two locations in Chicago, and it makes for a great spot for a casual, but delicious dining experience.

Best Chicago Bars

Two Dots and a Dash (pictured above) Under the streets of Chicago is a tiki bar that will transport you away to somewhere warm and tropic. This Chicago cocktail bar features drinks served in beautiful glassware (flaming and group cocktails available), 200 rums, Polynesian bites, and funky retro tiki vibes. I’m beyond obsessed with this bar and I bet your booty you will be too!

Revolution Brewing is one spot that I was so bummed I did not have time to visit. This Chicago brewery is Illinois’s largest independent brewery, and I’ve heard great things about their brews. Next time, though! And if you go, do let me know how awesome it is!

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Now it’s off to you! Time to start planning your trip to Chicago!

Things To Do in Chicago
Things To Do in Chicago
Things To Do in Chicago

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