5 Reasons Why You Need to Visit Chicago

You know a vacation is good when you get home and start researching deals to go back… now more than ever, Chicago is such a magical place to be. If you’re craving the city life but want your dollar to stretch a little further, this is definitely the place you need to be.

I first ventured to Chicago about two years ago after graduating college with some of my best friends. Our time there was short, leaving me with the desire to explore more of it. It may have taken a little while to get back, but I’m SO glad that I did.

We booked our vacation just a short 10 days in advance of our departure.  I had the vacation time approved since September, but couldn’t decide on where to go. November is not known as an ideal time to travel for most cities, but we took our chances. And it’s not too late for you to take one, too! Below are some of my favorite highlights of the trip and why you should visit too.

  1. The restaurant scene… WOW
    • When you’re sad about being full because you want to try more food: talk about first-world problems. Here are a few places we went to that I still dream about
      • The Kitchen: I had one of the greatest gin gimlets ever here. And I’ve had a lot of gin gimlets in my day. The bartender filled me in on a secret: they infused the gin with cinnamon sticks + apples to give it a fall flair.
      • Eataly: one of my favorite parts about Chicago is that it has all of the same major restaurants and flagship stores as NYC, but they’re not as busy. Eataly NYC was so popular that they had to build a second one. If you’ve never heard of it, it’s basically a giant, multi-story Italian market with several sit-down restaurants planted in the middle of it all. The energy here is inspiring, and leaves you feeling like you’re part Italian.
      • The Allis: located on the first floor of Soho House–which is normally a member-only spot–the Allis is a public coffee shop. Although I’m not sure what the buzz is about with Soho House and its exclusivity, The Allis is totally worth the trip to this side of the city. At night, like several other Chicago coffee shops, it turns into a bar (win/win).
      • AMK Kitchen: one of the most difficult decisions I had to make while in Chicago was where to eat brunch. After some deep research on OpenTable, Yelp, and various other websites, we finally landed on AMK Kitchen. Let me just say, although Chicago is in the midwest region of the U.S., they know how to make a pretty darn good chicken n’ waffles.
      • Revival Food Hall: after the opening of The Hall on Franklin in Tampa, I became a little more acquainted with this unique and trendy concept. While on the way to Willis Tower, we caught a glimpse of this gem and immediately fell in love. Any place that serves gourmet sandwiches and Tito’s Vodka + Mint Lemonade is always a good decision.
      • Molly’s Cupcakes: imagine a place that has delicious cupcakes, rope swings attached to the bar, and 90s rap music on repeat. A few things that you had no idea would work so well together… like a creme brûlée cupcake and Tupac.
      • Gino’s East: no one comes to Chicago and doesn’t get deep-dish pizza. Like the brunch situation, we were unsure of where the best slice would be. Luckily, we had a friend who gave us an inside scoop on where to go. Gino’s East is a super laid back restaurant that’s covered in signatures of previous visitors. And I’m not gonna lie, I’m a little sad that I didn’t sign too. One small pizza between the two of us was enough to make the walk home a struggle (but so worth it).
  2. Great deals on flights–even greater last minute prices
    • As I mentioned earlier, I booked our trip 10 days out and still managed to get an incredible deal on Expedia. On our first day there, we got upgraded to have an additional queen bed in our room so we joked with a friend about flying up to join us for the weekend. Out of curiosity, I searched roundtrip flights leaving the next day, and it was $76 !!! For Cyber Monday, Expedia has a ton of deals that are worth looking into. I just checked the dates for Fri, Dec. 15 – Mon, Dec. 18 and found an awesome hotel + flight package for as low as $250 per person! I’m telling you, people, you need to take advantage of this.
    • We stayed in the Wyndham Grand Chicago Riverfront and flew nonstop with United + American on the way back for just $499 per person. The staff was so incredibly friendly and accommodating, and you just can’t beat these views. This is definitely the area you want to be in.
  3. Winter Wonderland
    • Visiting Chicago in mid-November was such a tease for Christmas!! As we strolled down Michigan Avenue, we’d see everyone so hard at work as they wrapped lights on every tree and designed their new window displays. On the bright side (or cold, that is), we were there for the very first snow of the season. Seeing the snow form a white blanket over the fall leaves was such an incredible sight that I’ll never forget. As Floridians, we stuck out like a sore thumb as we were the ONLY people brave enough to walk down the street while it snowed and actually enjoy it. Although these holiday destinations weren’t open for our visit, I highly recommend them:
      • Ice skate at The Ribbon in Maggie Daley Park
      • Sip wine and enjoy the views from your personal IGLOO at the City Winery on the Riverwalk
      • Zoo Lights at Lincoln Park Zoo
      • Ice skate in Millennium Park (and check out the breathtaking Christmas tree)
      • Christkindlmarket
  4. Walkability and transportation
    • Despite the fact that it was under 40 degrees for the majority of the weekend, this city is so lovely to walk in! We walked to most of our destinations, and for those that were beyond walking distance, we took the bus or train. If you fly into Chicago O’Hare, you’ll more than likely take the Ventra to avoid the $40 Uber/Taxi. Instead of just buying one ride, buy the 3-day pass. It’ll encourage you to explore all over the city, and do it with ease.
  5. Rooftop Bars
    • Chicago is home to one of America’s greatest skylines. What better way to take in the views than with a drink in your hand? For those of you who are afraid of heights, that should help give you a little liquid courage. Below are some of my favorites, including two that aren’t on rooftops but are worth mentioning!
      • LH on 21/LH on 22: LH, short for London House, was our hotel neighbor. We decided to check out the rooftop bar since we don’t get too much of that in Tampa. We learned that a day of snow results in a closed bar… makes sense. Luckily, you could still grab a drink at LH on 21 (the indoor bar) and take the stairs to 22 to admire the city views. Ben was very resourceful by flipping the seat cushions over to get rid of the snow, then proceeded to build snow mounds for our drinks to stay cold. It. Was. Awesome.
      • Cindy’s: located on the 13th floor of the Chicago Athletic Association Hotel, Cindy’s is known for its great views of Lake Michigan and beyond. This is a great spot for after-dinner drinks or even weekend brunch.
      • Signature Lounge at the 96th: 360 Chicago is a popular tourist attraction on the 94th floor in downtown. Unfortunately, we visited on a “zero visibility” night so we couldn’t go. The ticket sales agent gave us an inside tip to go to the Signature Lounge, located two floors ABOVE 360 Chicago. The best part? It’s free! We took the elevator to the top, had a drink, and realized they weren’t kidding about the visibility. I felt like I was in the clouds. On a clear night, the views here would be amazing!
        • Side note: I’d highly recommend purchasing a CityPASS. Not only did this get us admission to all of the city’s greatest attractions, but we actually got VIP access/add ons to most! It really helped to enhance the overall experience.
      • Three Dots and a Dash: quite the opposite of a rooftop bar–this place is located in what seems to be the basement of a building. It’s a cross between a speakeasy and a tiki bar. Don’t second guess where your GPS is telling you to go; it’s located in an alley. It gets pretty busy, it’s best to go on a weeknight.
      • Pops for Champagne: also not a rooftop bar, but so cute! I visited this place during my first trip to Chicago in 2015 and loved it so much that we had to go back. It could be because I’m a sucker for champagne, but I love this spot. The bartenders were so friendly and willing to make cool, off-the-menu concoctions for us.


So I may have gotten a little carried away with these recommendations… but there seriously was not a bad place that we visited while in Chicago! I hope this helps you if you find yourself in the city, wondering what to eat, where to go, what to see.




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