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  • Writer's pictureThe Killorans

A Weekend in Chicago

Chicago, Illinois. The Windy City. The Second City. The City by the Lake. The City of the Big Shoulders. Whatever you know it as, Chicago is definitely a city to add to any traveler's list to visit. Whether you're excited to have deep dish pizza or experience some of the more cultural activities, you will not be disappointed.

Paid time off can be hard to manage in just a short year, so we tend to plan weekend trips around various areas in the US a few times a year just so we can get in some travel without eating into all of our days off. Most people ask us whether we ever work or not - we do. How else would we be able to afford travel? We are just very intentional with our travel plans and will spend the energy to take a quick weekend trip somewhere so we can experience someplace new. A lot of times if one of us has a work trip at the beginning or end of a work week, we will tie in personal time the weekend around it. Chicago just happens to be one of those places.

If you're planning a weekend trip to Chicago, we have a few items that we would highly recommend and also lightly suggest skipping if it doesn't spark your interests. With a late flight in, our Friday was practically a dud but we were able to pack in quite a bit on a Saturday and Sunday. The key is having a nice hotel to stay at in a convenient location and you will be good to go.



If you're a coffee lover and enjoy fresh roasted coffee in a fun little shop, you have got to try Intelligentsia Coffee. They have amazing coffee, wonderful iced mochas, delicious pastries (we shared a chocolate croissant) and breakfast tacos with fresh salsas that really hit the spot when you weren't able to catch dinner the night before due to a late flight in. We highly recommend giving this place a try.


If you're new to the Chicago area and want some really thoughtful history on the city, including food and architecture, we recommend you try out Free Tours By Foot for a free walking tour of part of the city. We chose to start off our day with the 10 am Loop and Millennium Park tour with Andy, who actually gave great insight while keeping the tour light and informative. It's approximately 2 hours and definitely a great use of time. The tour starts right underneath the old Chicago Theatre. With the tour starting early, the lights on the sign aren't fully lit, so you'll have to come back later in the day to see the theatre in it's full glory. They do offer tours inside the theatre as well, but this is separate from the walking tour itself. Two of the aspects of this historic building that we loved the most were that it is modeled after the Arc de Triumph and; when the theatre was opening, Frank Sinatra was first to perform and signed his name along the back wall of the theatre. Since then, every single performer who graces the stage will also sign their name on the same wall.

Here's a look at a quick map of the area showing several of the stops we had:

Without this tour, you likely will miss a lot of fascinating sites. One in particular was inside of a Macy's near the Chicago Theatre. We wouldn't have thought just walking into a department store that we would see some extremely interesting and beautiful architecture. With the light wells and intricate detailing hidden within the structure, it's a great stop. It's a fairly easy building to spot but if you look for the green clocks at two corners of the building, you'll know you're there. Just don't forget to look up when you walk in.

One thing we forgot to go back by and see during the evening was Chagall's Four Seasons art installation in the Plaza near the disorienting Chase Bank building. This art installation is designed around the seasons made up of tiny mosaic tiles and, when you visit it at night, it's lit up and appears to sparkle gold. It was still pretty impressive during the day, but we wish we had stopped by during the evening to check it out.


Lunchtime was up and where else do you stop in than one of the most famous Chicago-style hotdog joints in the city - Portillo's. We hadn't really had a true Chicago-style hotdog and, though this place seems a bit crazy because of the almost market-like setup, it was fairly quick. If you haven't had one before, you have got to try one when you're here. And if you aren't super familiar with what they are, they are hotdogs covered with a whole pickle spear, sport peppers, sliced tomatoes, chopped onions, relish, mustard and a topper of celery salt all on a poppy seed bun. Pretty delicious.


If you're into Art and love to see some classics, then head on over to the Art Institute of Chicago. You could spend all day here but if you want an abbreviated version, you can knock out quite a bit in one afternoon. We made it over at about 3:00, with the museum closing at 5:00, but it was so worth the trip. As long as you know what type of art you like, you can manage to see everything you want in a short period of time. Ideally, it would have been nice to have an extra hour, but we got our money's worth in just 2.

Most everyone has seen Ferris Bueler's Day Off and knows the famous pointillism painting of Georges Seurat known as A Sunday on La Grande Jatte. It really can be something of a sight to see this painting in real life. All of the millions of dots of color painted onto the canvas to create a vivid park scene is really quite impressive. Even his border work is impressive, which from this photo, you can barely see!

Overall, the pieces displayed at the Art Institute, in our opinion, are some of the most impressive pieces you can see up close. Specifically, the Self Portrait of Vincent Van Gogh from 1887 really pulled us in for quite some time. We stood in awe of his layering and play on complementary colors through his brushstrokes which create such an interesting three-dimensional aspect that draws your eye from any angle throughout the room. It's absolutely fascinating.

If you're interested in art, we highly recommend to spend some time here to take it all in, however long that may be.


Right at 5:00, the museum essentially escorted us out of the galleries, letting us know it was time to leave. Luckily, just across the street from the Crown Fountain, we stumbled on a really great bar/restaurant called The Gage.

We were able to find a seat in the bar area and had some fancy cocktails (the Smoke and Mirrors margarita + the Far and Away sparkling rose mixed drink) with some PBR fried pickles to pick us back up from all of the walking around the city. The place was fairly crowded, full of people dressed up ready to go to a show, others casually catching up with friends and tourists like us taking a much-needed break from the city.


As mentioned earlier, the key to a successful weekend trip to a big city like Chicago is having a place to stay within a good walking distance of the areas you wish to explore most. Since we walked around all day, it was nice to be able to stop back by our hotel to relax for a bit before heading out for the evening. From our experience staying in cities all over the U.S., we have found we love the Kimpton hotel chains and the Hotel Allegro off of West Randolph Street and La Salle was no exception. Conveniently located in the middle of practically everything, just a short walk, Uber or train ride away from getting to our final destination. Each location is unique, decorated like a boutique-styled hotel, has a nice complimentary happy hour, fruit water available at all hours, is super clean and always has a hip vibe. Look it up and try one out - you won't be disappointed!


Once we were well rested, we made our way via the train several blocks North to Eataly, an Italian-style market with restaurants, wine, foods and desserts for purchase. Most everyone we talked to about Chicago raved about this place and it was nice to experience. However, it probably would have been better had we lived in Chicago and picked up fresh pasta, cheeses, bread, and produce to cook at home.

We were told you go from stall to stall to try different foods, but we must have done something wrong because it seemed like you physically had to sit down at each place like a restaurant and order food accordingly, which takes forever. Everything we had was pretty tasty, including the cheese and charcuterie, but we probably could have done without it.


After killing a few hours indulging at Eataly, we were on our way to the main event of our evening - The Second City. If you've never heard of Second City, you should look it up. Loads of famous comedians who have been featured on shows such as Saturday Night Live got their big start from Second City, with locations in LA, Chicago and Toronto. People like Mike Myers, Dan Aykroyd, Amy Pohler, Tina Fay, and so on and so forth.

This comedy club offers a couple of different acts that you can go see. We went with a couple of friends to see The Gaslight District - an improv comedy show held Thursday-Sunday nights. We went to the late show at 11 and we laughed so hard we were hoarse the next day. Our recommendation is to be sure to get there well before showtime to get seats (they're assigned on arrival) and, if you're seated way off to the side like we were, just simply ask and they may move you (we got moved to the second row, dead center). Also, never ever sit on the front row unless you don't mind getting selected to be pulled on stage and henceforth be teased throughout the show. These comedians were fresh, hysterical, and surprising. We cannot wait to see where they end up next!

Fun Fact: Our Free Tours by Foot tour guide Andy told us he writes comedy for Second City, which is pretty awesome, though he didn't write for the particular show we saw. If and when we make it back to this city, The Second City is definitely a destination we plan to visit again.

And with that (and an interesting late-night Uber ride back to the hotel), Day #1 was complete.



Day 2 and and still so much to see.

To change things up a bit, we decided to head on over to one of the more highly reviewed donut shops across the river and give homemade Chicago donuts a try for breakfast! The Doughnut Vault. They have a very specific menu and will serve donuts and fresh coffee until they run out, so you've got to get there early enough to get what you really want. Just located around the corner from the famous Merchandise Mart, this tiny little shop has just enough space for a small line to form and then it begins to wrap the building. And when lines begin to wrap buildings, you know you're in a good place. Let us tell you these donuts were delicious! From top left around to bottom right, we tried a Chocolate Glazed, Buttermilk Old Fashioned (which seemed like the one you have to try if it's your first time), a Vanilla Glazed and their special of the day - Wedding Cake. Unfortunately, they were out of the Seasonal Jelly Doughnuts, but the rest were so tasty, as well as the hot and iced coffees we ordered. Definitely enough food for 2 for breakfast, especially if you're wanting a little something sweet.


With the river so close by on the other side of the Merch Mart, we decided to follow the stairs down to have our own free architectural tour along the river.

If you love skyscrapers and a unique point of view, walking along the lower level of the river is awe-inspiring. The buildings feel so huge from below street level and the walk down to Lake Michigan, rain or shine (we walked in the rain), is something you've got to do at least once in the city. Fog and all, it can be quite an impressive site for any traveler.

Plus, once you make it to the Lake, you're greeted with either the Ferris wheel of the Navy Pier to the North or the Chicago skyline from the boat docks to the South. It was foggy the day we strolled by the harbor, but it made for some pretty neat scenery, welcomed us with greetings from dozens of geese and kept the day nice and cool for June.

From this approach back to the city via Millennium Park, cut through Maggie Daley Park (which is advertised as a "family-friendly" park because they have big play areas, rock climbing, mini golf and the like, but really we highly recommend you take a stroll through it). Not only is it lush and green and clean and beautiful, but you also get an un-bastardized view of the skyline. Plus, if you do have time to spare, there are plenty of activities to do here, by yourself or with groups of people. It was wonderful and totally worth the walk.


By this time, you might be beginning to work up an appetite for lunch. If you have yet to try real deep dish pizza, now is your opportunity. It'll be getting close to the lunch rush, and the trick to ordering deep dish pizza at one of those many restaurants you read about in reviews (Lou Malnati's, Pizzaria Uno, Giordano's, Gino's East) is to get there when you aren't quite at your "I'm ready to eat" stage but really when you're at that "food is starting to sound like it would be a good idea in the next hour or so" stage. Once you arrive, most places have you place your deep dish pizza order before you're even seated. You just wait around for a bit to be seated (we walked around outside at a nearby fountain) and not long after you get a table, your pizza is ready to go. Seems foolproof but it does take some time, so don't plan on a quick meal.

And folks, deep dish pizza really is no joke. If you do plan to have a few bites of some appetizer or snack before indulging, know that you should order a personal to a small size, depending on how many people you're sharing with. We decided on a small, though we definitely could have ordered a personal size between the two of us, due also to the fact that we split an appetizer and salad (in an effort to get some greens into our overloaded cheese lunch). We only got through half of the pizza when it was all said and done.

Of the places we've eaten at in the past, we had tried Uno and Lou Malnati's. Our Tours by Foot guide, Andy, offered his recommendation of all the deep dish pizza joints in the city and suggested Giordano's, so we figured why not. It seems like a very touristy place, which it was, but he said of the other locations around, this was his favorite. But really, in the end, it's all deep dish pizza. It comes out hot, extremely cheesy, and saucy.

Though we could understand the whole rage of it all, we decided after having a deep dish together, deep dish really isn't our thing. We're glad we shared one, but next time we visit, we will forego the pizza. We'd still go eat Italian, just not deep dish. If you haven't tried it yourself, though, you have to do it at least once.


Time to walk off all those carbs.

We strolled back on over to Millennium Park to see the bean one more time, but in the rain.

This structure is so interesting, and watching the way people interact with it is always entertaining. It was designed so that when you stand just to the left of where this photo above was taken, you get a full 360 degree view of continuous skyline. In this view, you can see how the trees over to the right alter that vision. But, most of the time, it's just people taking pictures of their reflections on different angles of the bean or selfies with the bean in the background.

We're no exception to that stereotype.



With our adventure winding down and an impending flight out to get back in time to start the work week over, it was time to say goodbye to Chi-Town. Chicago. The Second City. Though we barely scratched the surface, we packed in some pretty memorable experiences that we wouldn't change for the world. Chicago definitely has a lot of character, is full of nice people, is extremely walkable, a little unpredictable when it comes to the weather, and is overall a very pleasant place to be. There's definitely a lot to see and if you're planning a weekend away, do yourself a favor and plan maybe 1 thing ahead of time (for us, that was Second City), get there and just see where the city takes you. You'll be surprised at some of the fascinating things you can encounter.


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