Welcome to Chicago

The windy city is blustering with excitement.

And we can't wait to share it with you

There is nothing quite like the Windy City in any season, even though Winter can be quite frosty. Baseball, snowball fights, epic parties in Wrigleyville, there is nothing like Chicago. If all else fails, grab a brew and Save Ferris!

We can't lie, we are partial to the summer months but take this guide and enjoy this city as much as we do. 

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What to See

The iconic skyline of Chicago is filled with unforgettable memories and exciting activities just waiting for you.

  • The Sears Tower Observation Deck: there is a glass floor so you can see all the way down 108 floors!

  • Goose Island Brewery Tour- The Brewery tour includes a beer tasting, it also has a restaurant so you don’t get too hammered while tasting.

  • Chicago is known for its Architecture. The Architectural river cruise is an amazing way to see a lot of the city and learn its history.

  • The Bean in Millennium Park is a must see in Chicago.

  • Also, if you like Improv the Second City Theatre has pumped out some major legends, Tina Fey, Amy Poehler, Chris Farley, Chevy Chase! Also Check out the Improv Olympics.

  • There are hundreds of tours to take, including a helicopter tour! Pick the right one for you and get exploring.

  • If you are on a budget or aren't about paid tours, a walk down Michigan Ave or the Magnificent Mile. The more upscale area filled with amazing restaurants and shops.

  • The Navy Pier is a great spot filled with rides, restaurants, and boutiques.

  • Shopping: You can find everything you want and more on Michigan Ave. There is a Nordstrom, All Saints, pretty much it is like the 5th Avenue of Chicago, there is also a Mall at the John Hancock building!

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Where to Eat & Drink

Have you heard of Chicago-style Deep Dish pizza? Yeah, us too.Chicago is known for its food and we had no problem testing that out .

My number one suggestion is to download the app Infatuation, it is a food blog out of New York, they have since expanded to Chicago, LA, and San Francisco (I’m not going to lie, I hope they appreciate this shoutout.)

  • But first there is brunch—Wildberry Café home to my personal favorite Red Velvet pancakes….like they are a real life dream come true in your mouth. I could never love anything more, they also have a biscuits and gravy eggs benedict! I wish that I could go on and on about this place, but it would be unfair to the other restaurants.

  • Le Colonial is your go to spot for Vietnamese food.

  • Giuliana and Bill Ransic own both RPM Italian and RPM Steak….I know what you are thinking eww gross another celebrity restaurant, why are you so obsessed with Celebs! I am obsessed with Celebrities, but I can attest that RPM Italian hosts probably the best meatballs I have ever had in my life…hands down, RPM Steak is amazeballs as well. It is definitely a must try, they are pricy but worth it. Everyone deserves one nice night out while on Vaycay.

  • Another great steak place, that is pricey but amazing is Chop House.

  • Howells&Hood and Rock Bottom ( a chain but still worthy) both have great Beer Flights.

The Windy City

We have so much in store for this beginning guide. We cannot wait to expand. But you'll definitely be drunk by the end of this one.