Weekend Trip: Chicago
Chicago, Chi Town, the Windy City, whatever you call it, at least you’re callin'.. am I right? Chicago is known for its chilly temps, deep dish pizza, and interesting architecture, but after visiting for a weekend I came to the conclusion that Chicago is insanely underrated and there is so much more than meets the eye.
To me, Chicago seemed like a miniature, well-kept version of New York City. Don’t get me wrong, I love New York City, but I’d be willing to say that I enjoyed Chicago even more. The locals were friendly, the food was amazing, the city was trendy, and the views were to die for. I also had the pleasure of visiting when temps were in the mid 70s, so my perception may be a bit skewed, but I would 10/10 recommend visiting Chicago.
If the Windy City is on your travel bucket list, sit back and engulf yourself in the culture with these Chicago must-sees:
Places to Grub Out:
Brunch- I’m a huuuuuge brunch gal. Mimosas and eggs benny? You better believe I’m there. Brunch is an art form, one that no day is complete without, so put these two places on your to-do list.
Troquet- Located at the bottom of Hotel Felix, this trendy brunch escape serves bottomless mimosas with an entree for $29! (If you’re reading this in Burlington, NC that probably sounds like an absurd amount to spend on breakfast, but remember that we’re talking about big city prices here) Troquet has outdoor and indoor seating perfect for any weather.
Beatrix- Situated smack-dab in the middle of the city, Beatrix is the perfect quick-stop brunch place for your long day of adventure. The atmosphere and menu has a farm to table vibe, serving up healthy breakfast options that won’t bog you down as you explore all day. We arrived around 10am (we shamefully slept in) and the wait was around 45 minutes, but we sat at the first-come-first serve bar. Definitely call ahead to make a reservation!
Lunch- Deep dish pizza and Chicago-style hot dogs are famous staples, ones that no trip is complete without. I surveyed a number of locals and these restaurants won the popular vote and to no surprise, they surpassed my expectations. If you’re only in Chicago for a short period of time and want to try them both, take some notes from Ashlyn and I.. Just pull the “I’m only here for a few days” card and bring your hotdog to eat as an appetizer while you wait for pizza. *tourists*
Portillo’s Hot Dogs - This place has 4 mini-restaurants packed inside and serves an array of different types of food. Portillo’s also has multiple locations around the city and has a fun family-friendly atmosphere.
Lou Malnati's- Just listen to how authentic the name sounds. It sounds like a Chicago mobster is in the back whipping up the most authentic pizza you’ve ever eaten, tastes like it too. A medium pizza costs around $15 but is big enough to split. There are multiple locations around the city so just add it to your Google My Map and find the closest location.
Dinner-
The Signature Room on 95th- If you’re afraid of heights, this may not be the restaurant for you, but if you’re a thrill seeker, check this out! Situated on the 95th floor of the John Hancock Building (the 6th tallest building in the US), this elegant restaurant provides 360 degree panoramic views of the city. The walls are all glass windows and every seat has a breathtaking view, which explains why this is the most instagrammed place in Chicago. I ordered the tortilla soup and we split the roasted veggie plate appetizer and my bill came out right at $25. You can definitely spend a pretty penny in here, but there are options on the menu for those of us balling on a budget.
Snacks-
Best Views in Town-
Rooftop Bars- No trip to a city is complete without relaxing at a rooftop lounge. There was no shortage of rooftops in Chicago so we bounced from rooftop to rooftop. My favorites include:
Trump Towers Terrace or the London House. These two are directly across from each other and overlook the riverwalk. The London House had a more party-goer feel in comparison to the Trump Towers Terrace which was more laid back and swanky.
Drumbar- Take a trip back in time at this speakeasy style 1940s themed lounge. The menu features eclectic cocktails, including one with egg-whites mixed in.. we were very intrigued. The outside terrace has fire pits and tons of space. This bar is just a block away from the Signature Room on 95th so stop by there for a pre-dinner cocktail.
Cindy’s Rooftop- This rooftop bar overlooks the famous Chicago Bean. The line can be pretty long so try making a reservation in advance.
Lookouts-
SkyDeck- I am a daredevil and am not scared of much.. But HOLY CRAP this was crazy. If you think this looks scary, multiply that fear by about 500 and then you might understand the feeling you endure when you step out on the ledge. Being able to see 103 stories below and have a view that spans up to 4 states is a sensation you can’t explain unless you try it for yourself. Don’t ask how I did the handstand because honestly, I was shaking like a leaf afterward. Tickets cost around $25 to visit the lookout, but I’ve seen coupons floating around the web if you book online beforehand.
Travel hack: If you’re not really into stepping out on the platform or paying for the $25 elevator ride, but you want the awesome view, there is a restaurant on the 67th floor of the same building. You can go and pay the $25 to get a few drinks and have almost the same view as the SkyDeck.
Instagram VS Reality
Things to Do-
Michigan Avenue Shopping- Part of Chicago’s elite Magnificent Mile, Michigan Avenue features shopping of all ranges from Forever 21 and Zara to Cartier and Tiffany & Co.
The Bean- To many people’s surprise, including my own, the bean is actually named Cloud Gate. There isn’t much to do other than walk up, knock on it, and take obnoxious touristy-pics around it, but what else is vacay for?? Cindy’s rooftop is right beside the Bean so once you work up an appetite taking so many pics, head over for a drink.
Navy Pier- This is more of a suggestion for families or if you’re looking to kill some time between rooftop bars ;) The Navy pier is Chicago’s lakefront treasure jetting out 3,300 feet into Lake Michigan. The pier is the home of many carnival-style rides like a giant ferris wheel, a Drop Zone, carousel, and more.
Riverwalk- Walk along the Chicago river for beautiful views of the city and many options for dining. We stayed in the Sheraton Grand which was right along the river, so the riverwalk was our north star when navigating Chicago.
I could go on for days about Chicago and how great it was. Getting around Chicago is very easy as Chicago is a walkable city, but if you’ve had a few mimosas and don’t feel like walking, Uber and Lyft shouldn’t be more than $7 to your inner-city destination. Keep in mind that there are two airports in Chicago so make sure to check your boarding pass to ensure that you don’t end up at the wrong one. I was only there for 2 days so I wasn’t able to do everything on my list of to-dos, so a few honorable mention things are drinking on Hubbard Street, architectural river tour, Au Cheval burgers, the zoo (it’s free!), and Second City Comedy (a comedy club where many SNL stars began their careers). If you have any questions about my time or would like more recommendations, feel free to tweet at me or message me on Instagram!
Happy Travels!