A (Early Spring) Travel Guide to Chicago

Chicago, Chicago, what a place. Chicago and its neighboring suburbs have over 9.5 million residents. With so many people, every experience is different and you’ll always get different suggestions. These are just the things that I like doing and highlighting to my visitors, but if you have another activity you enjoy please let me know in the comments. I love finding out new things about my city!

First things first - food. Chicago has many signature dishes that visitors have to try. Once my boyfriend, Parish, got off the plane, we headed straight for Lou Malnati's. There’s a lot of options for deep dish pizza: Uno’s, Pequods, Giordano’s; but this place is one of my favorites. Their house salad is also one of my favorites.

Parish also really wanted to try an Italian Beef. There are a few places to do this. I took him to Portillo’s. I’ve never had anything I didn’t like at Portillo’s - hotdogs, onion rings, chopped salads, chocolate cake, ribs. I’m not kidding - it’s all good! I always go for the chopped salad, but you won’t regret anything you order there. Johnnie’s Beef is also a great place to get beef if you find yourself in the suburbs.

If you’re ever feeling a little fancy but are unsure about where to eat in the city, Lettuce Entertain You restaurant group has great options. They own restaurants with all different kinds of flavors all over the city. Beatrix, Wildfire, Joe’s, and so many more restaurants are part of this company and are all super tasty! Over the weekend, Parish and I tried one I’ve never been to. Ēma is a more Mediterranean feel with hummus and small plates. I had never heard of it, but knowing it was a Lettuce Entertain You restaurant, I figured it was worth a try. The brunch was delicious!

I titled this blog post “early spring.” Although the food is available all year round, activities shift depending on the season - if you can brave the cold! This trip, Parish and I did both outside and inside adventures because the weather was bearable. However, you never know with this time of year. One day it can be 65 and sunny and the next it can be 23, windy and snowy.

Friday afternoon we headed to the Chicago Art Institute. There’s so many great museum options but for what we wanted to do for dinner and drinks, the Art Institute made the most sense geographically. There’s so many famous and amazing works of art that you realistically need a few days to take it all in. Rodin, Picasso, and O’Keeffe, all have Other museums I highly recommend include the Field Museum, the Shedd Aquarium and the Museum of Science and Industry.

The Art Institute has an impressive Modern Art Wing that is connected to Millennium Park by a bridge. If you’ve ever had a friend go to Chicago, chances are they shared pictures of Millennium Park. It’s home to Cloud Gate, which you might know as the Bean. I had to be a good tour guide and make sure Parish had his touristy pictures with the Bean. (He was also a great stand-in photographer for Kristen. #instagramboyfriend)

We wanted to go warm up inside. I thought a great place to show Parish was the Chicago Athletic Club. The Game Room in the Chicago Athletic Club used to be a men’s only club and now is a beautiful hotel with many accents of its history. The beautiful old Chicago architecture can be seen in the lobby as well as the Game Room. The Game Room is on the second floor. You can have signature cocktails while playing on their full-sized, indoor Bocce Ball court or slide in one of the many cozy booth areas and catch a game. I loved taking Parish there because it’s one of my favorite bars in Chicago.

I also love showing people the different styles of architecture in Chicago. Since the boat tours of the city don’t usually open up until about about mid to late April, a quick and easy way this time of year is to go through the buildings on your own. I love showing people the Palmer House Hotel. The detailed and decadent design is perfect to take in while sipping a cocktail in the lobby. Walking by the Chicago Board of Trade building and seeing the statue of Ceres atop the building is another great piece of Chicago history. I would have to say my favorite building is the Wrigley building along the river.

I grew up near the Frank Lloyd Wright Oak Park studio, but had never actually gone on a tour of the home in the area. Parish and I went this past weekend. The rates are super fair and it’s a really easy way to see some history! I think the more travel guides I do, the more y’all will come to realize how obsessed I am with history!

After the Game Room, I took Parish to Italian Village. This traditional Italian restaurant is so old school they don’t take reservations! It’s frequented by play goers, since Hamilton is being performed down the street. The restaurant is set like an Italian village - complete with a starry night scene with twinkling lights, and little alcoves with a more private dining experience. The service is professional and the food is delicious!

Saturday was St. Patrick’s Day, Chicago’s version of Mardi Gras. The whole city celebrates and we even dye the Chicago River green! We headed down to the city to the River North area. When people ask me about being from Chicago, they usually ask what the most popular bar is, and like I mentioned before, since the city is so big and there are so many different kinds of people, you’re always going to get a different answer.

I would say that when I think of going out, I think of three areas in particular: Wrigleyville, Old Town and River North. We decided to hang out by River North since that is where they dye the river green. The Riverwalk was open even though it was a cold day so we got to see the river up close and personal. The Riverwalk is a relatively new achievement for the city. Open in the warmer months, this area is as you might guess, along the river. There’s a wide variety of restaurants and bars that line the Riverwalk so you can either walk down or boat up to the dock and hang out. We hung out for a while by the river before heading to get some food.


The bars were super packed and had really long lines, so we did not really try to go in anywhere, however the House of Blues was open. The House of Blues is easy to distinguish by the pringle-like roof. We went in there, had some green beer and enjoyed the live music. We bar-hopped a little bit before heading home. Getting home in one piece was truly the luck of the Irish.


No matter what time of year you come visit, Chicago always has something to offer. This is only a small sliver of stuff that we fit into a weekend in the late winter, early spring. But I hope that as the seasons change I can continue to show you guys more of this city. Come the spring and summer months, my friends and I will be going to Cubs games, the Oak Street beach, and probably spending more time outside in general! But until then, I will be bundled under many blankets with an extra-large mimosa. Cheers!


To new beginnings and new friends. Cheers!