Chitown. Where the wind is fierce & the city is too.

Not gonna lie. Chicago has become my favorite city in the last 1.5 years.

I just made my fourth trip there in less than 2 years and I just can’t get enough of it! I love that you can be in the heart of the city surrounded by skyscrapers and 5 minutes later, be looking out into the incredibly blue waters of Lake Michigan. There is great food, friendly people, so much to do, local brews, constant events, architecture beauty, and much more that the city has to offer. Because I love this city so much, I’m going to overwhelm you with a TOP 10! In no particular order…

  1. Architecture Tour
    Anyone and everyone will recommend going on an architecture tour. It’s one of the most popular tourist attractions, and for good reason. There are plenty to choose from, but I personally recommend Seadog Cruises. I booked the 75-Minute River & Lake Architecture Tour, where you ride a speedboat out on Lake Michigan and have an incredible view of the skyline and then receive the architecture tour down the river.
    Tip: Check out Groupon for discounted tickets.
  2. Comedy
    This is another no brainer that anyone who knows Chicago will tell you is a must. As it has been nicknamed The Second City and is a hot place for up-and-coming comedians, you can find many comedy clubs that will leave you crying with laughter. The two I’ve experienced and highly recommend are the properly named Second City and The Improvised Shakespeare Company. They are both very reasonably priced ($23 & up for Second City and $16 for Shakespeare) and completely worth your time & money.
  3. Millennium & Grant Park
    You can’t go to Chicago without getting your iconic picture with Cloud Gate, aka The Bean! Don’t forget to walk around the rest of Millennium Park; check out the Jay Pritzker Pavilion (and before your trip, see if they are having a free concert or movie showing!), marvel at The Crown Fountain (but don’t get sprayed), walk along The Lurie Garden, take the BP Bridge to Maggie Daley Park, and end your walk along Lake Michigan with Buckingham Fountain in view.
    -Tip: Go to the Bean in the early morning (and I mean like 8am) you can get much better pictures without a hundred other tourists there.

  4. Deep dish pizza
    The never-ending debate on the best deep dish pizza. Lou Malnati’s. Pequod’s. Giordano’s. Or, if you wanna go crazy and have a Pizza Pot Pie instead, check out Chicago Pizza & Oven Grinder Co. Because, you can’t go wrong with pizza pot pie. (But seriously, they’ve been on the Food Network, just watch this heart attack video). You should note that all the big deep dish pizza restaurants do NOT take reservations, but read below for some sneaky tips…
    -Tip: If you decide on Pequod’s, go online to their website 24 hours in advance and you can submit a Table Request, which means when you arrive, you’ll be moved to the top of the wait list. If you decide on Lou Malnati’s and there’s a long wait, have your group order your pizza when you put your name on the list and your pizza will begin cooking then instead of once you’re seated.

  5. Beaches, Lake & River
    The river and Lake Michigan are two landmarks that set Chicago apart and must be experienced. December may not be the best time of the year to check out the beaches, but even walking along Lake Michigan can be just as fun and have just as beautiful of views. If you are visiting during the summer, I highly recommend grabbing a blanket, some snacks, and a good book (or just people watch) and find a spot along Lake Michigan to relax. If you would rather be entertained by some high school and college kids, check out North Avenue Beach and grab a drink at Castaways. Or, you can take your own river cruise with Chicago Electric Boats, which is a company that lets you rent out a 10-passenger duffy boat to drive along the Chicago River at your own leisure. Did I mention it’s BYOB?
  6. SkyDeck at Willis Tower
    This is one tourist experience that is worth every penny. It’s not every city that offers a glass ledge 103 stories high. If you go on a clear day, you can even see Michigan on the other side of the lake.
    Tip: If possible, go on a weekday morning when it opens to avoid the long lines and crowds. You won’t wait nearly as long to get up to the 103rd floor, AND you won’t feel rushed to take a couple pictures and then jump out of the ledge (obviously, back inside the building).img_0731
  7. Museums
    The Art Institute, Field Museum, Museum of Science & Industry, Planetarium, Aquarium, the list goes on! My favorite that I’ve visited is The Art Institute but I don’t think you can go wrong with any of the above options, plus more. Definitely worth a visit and your time!
  8. Breweries
    If you’re not a craft beer aficionado like me, then you can skip this one. 🙂 If you love craft beer and checking out breweries, make sure to visit Goose Island Brewery (and schedule a tour before your visit) and Half Acre. I didn’t have a chance to visit Lagunitas or Revolution, so those are both on my list for my next visit!
  9. Wrigleyville
    I’ve never visited a city that had an entire neighborhood centered around their baseball field, but that’s essentially what Wrigleyville is. Head out there on a gameday and you don’t even need to go to the game to experience the excitement around there! With plenty of bars and restaurants to choose from, you can’t go wrong. And if you’re feeling some tropical cocktails & karaoke singing, check out Trader Todd’s; you’ll be sure to have a great time!
  10. Au Cheval/Small Cheval
    OMG the burgers. I haven’t actually had the privilege of eating a burger from Au Cheval, but they always pop up on the lists of best burgers in Chicago (and the country, and the world…). Au Cheval is known for having a good wait, but I’ve heard if you go to the bar right when their kitchen opens (which is at 5pm on Saturdays and Sundays) and hang out for a while, your wait time might not be as long…If you don’t have time to wait, then check out their sister restaurant, Small Cheval. A more casual feel, and with not as extensive as a menu, Small Cheval offers the stripped down menu of Au Cheval, with a much faster turnaround. And personally, it was one of the best burgers I’ve ever had!

    Honorable Mentions:
    Cindy’s Rooftop (for an insane view, delicious food and unique cocktails), Chicago Party Boats (check out their website for tickets to one of their Yacht Parties), and theWit for a rooftop bar experience.



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