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Welcome to the world through my eyes. I'm an internationally published travel writer and photographer who has travelled to 80+ countries, and has tried to capture some of that along the way. Travel means the world to me, and my goal is to offer tips and advice to help you feel the same! 

How to Spend 2 Days in Chicago - Your Chicago Trip Planner

How to Spend 2 Days in Chicago - Your Chicago Trip Planner

Chicago was a city I always knew that I had to visit in my lifetime, I just didn’t know when it was going to happen. It was funny, when I was planning my Chicago itinerary, it wasn’t so much excitement that I felt as much as relief that I’d finally be going.

You see, there are certain cities which are on my bucket-list which are in the “non-negotiable” category, and Chicago, for me, was on that list - meaning that at some point in my life I had to go.

Chicago is just a city that throughout my life, I couldn’t ignore. It just kept coming up again and again, and it attained a bit of a larger than life stature in my mind. Before even stepping foot in the city, I revered Chicago for its sports history, its music, its theatre, its food, and perhaps most notably for what Chicago has done from an urban planning standpoint that Toronto hasn’t (cough cough waterfront preservation).

Boarding the plane, I just had this pleasant yet subdued smile on my face. Finally,finally, it was time to experience all that Chicago had to offer.

Now, I spent longer than 2 days in Chicago doing research for this article, but I’m focusing on how to tackle Chicago in 2 days because I created a poll on social media, and most people were keen to learn what they could reasonably fit into a weekend in Chicago. And, to me, it’s all about providing value to my readers and followers.

So, this is a going to a busy, beautiful, and hectic two days in Chicago if you’re following this Chicago itinerary to a tee, but you’ll leave with a good feeling for the city. That, I promise.

NOTE: This post may contain some affiliate links. That means, simply, that I may get commissions from some of my recommendations. That being said, my opinions are fully my own.

What Should be on Your Chicago Itinerary If You’ve Only Got Two Days in Chicago?

If you’ve got 2 days in Chicago, you better make the most of it, that’s why I’ve got this Chicago trip planner.

Firstly, I want to stress that the following list reflects my ideal 2 days in Chicago, but it’s likely that 100 different people could come to Chicago and all have their own version of what a perfect Chicago itinerary looks like. That, in a sense, is what makes Chicago special.

I wouldn’t scold someone if they came to Chicago and just spent two days eating, nor would I scold someone if they came and spent two days in museums. There is no right or wrong way to do Chicago, but what I’ll aim to present below is a diverse, high-energy Chicago Itinerary to give you a taste of the city at large.

It’s going to be your ideal Chicago trip planner if you’re cool with running on caffeine and the energy of the city while there, then sleeping when you’re back home

So, let’s get started. What needs to be on the list?

The Art Institute of Chicago

You should include the Art Institute of Chicago in your Chicago itinerary if you’re spending two days in Chicago.

Whether you have one hour, one day, or one week in Chicago, you better make sure you visit the Art Institute of Chicago. I’ve been to Paris, but not to the Louvre, which likely means this is the most impressive collection of art that I’ve ever laid eyes on in person.

If you are indeed trying to tackle Chicago in 2 days, it’s fair to say that you could spend your entire time here, but to get a feel for a city, that’s likely not wise. The museum opens 10:30am daily, so I’d aim to come right when it opens and spend roughly 1.5-2 hours.

There are three sections that in my mind you’ve got to see.

Firstly, you need to see the Impressionism section on the second floor. Monet, Degas, Renoir, Cézanne, Caillebotte - it’s literally like the greatest hits of French Impressionism.

Also on the second floor, check out the Contemporary artworks. We’re talking Magritte, Pollock, Georgia O’ Keefe, Warhol.

Lastly, run on up to the third floor to see the Modern artworks. You’ll find Dali, Chagall, Kandinsky, and Picasso’s “The Old Guitarist.”

Let me be clear, what I saw in two hours there was incredible, but when I get the chance to go back to Chicago, I’ll spend at least a full day here. But, those recommendations are for folks who are limited on time, but still want to set their eyes on some of the greatest art ever created.

Here’s a little visitor guide if you’d like more info in preparing for your visit.

Try Chicago’s Signature Dishes

If you’re only got 48 hours in Chicago, be sure to eat a lot of food in Chicago!

Chicago is known for its food, and I’d say a few things in particular. I learned quickly that conversations about where to get the best (insert famous Chicago dish) can get hotly contested to say the least.

In general, I think it’s fair to say that Chicago is known for its deep dish pizza, hot dogs, Chicago mix popcorn, and Italian sandwiches, and you should try all of these dishes at least once (forget the diet in Chi-Town, please)

To try to be efficient, I ended up doing Bobby’s Bike Hike “Chicago Favorites Walking & Food Tour.” The tour was about 2.5-3 hours long, so it ran from 11:30-2, which allowed me plan activities on my Chicago itinerary both before and after the tour.

What I did like was that our tour guide Ben led us on a route that allowed us to see a fair bit of Chicago itself including The Loop, the Chicago Riverwalk, the Magnificent Mile, as well as The Pritzker Pavilion and Cloud Gate in Millennium Park. Throughout the tour, he was both knowledgeable and personable.

We got deep dish pizza at Giordano’s, which was excellent and a spot that was recommended to me by many readers and followers before I left for Chicago. Our Chicago Hot Dog was by a relatively nameless spot by the river, and, quite honestly, I feel like it was just a spot that happened to be along the route (that was the one big miss of the tour), Our Italian Beef Sandwich from Bongiorno's Cucina Italiana & Pizzeria though was delicious, and a spot, like Giordano’s, that was already on my radar.

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Other spots that you may want to try Chicago deep-dish pizza include Pequod’s Pizza, Gino’s East, Chicago Pizza and Oven Grinder Company and Lou Malnalti’s Pizzeria. If you can only choose one, I’d go with Pequod’s.

Other spots that you may want to try a Chicago hot-dog include Hot “G” Dog, Portillo’s Hot Dogs, Jimmy’s Red Hots, and Superdawg Drive-In. If you can only choose one, I’d go with Portillo’s.

Other spots you may want to try an Italian beef sandwich include Al’s Beef, Ricobene’s, and Johnnie’s Beef. If you can only choose one, I’d go with Ricobene’s.

If you’re enjoying this post, you’ll love my post on the Most Fun Things to do in Cleveland or on the Village of Rhinebeck, New York!

A Cruise Down the Chicago River

Taking a Chicago RIver Cruise is definitely something you should do if you’re trying to tackle Chicago in two days.

This was hands down the highlight of my trip to Chicago, and it’s hard to imagine that it wouldn’t just instantly become the hit of your Chicago vacation.

Architecture is something that deeply fascinates me (especially a skyline like Chicago’s which shows classic examples of so many styles), and so I did Chicago’s First Lady’s Architecture Tour. They’re the only Chicago River cruise that’s partnered with the Chicago Architecture Center (CAC), so that was a selling point for me.

I got a seat on the top deck, and the following 90 minutes were spectacular. At times, some of the information from our guide lacked a little energy or pizzazz, but she was truly an impressive wealth of knowledge as to the city’s architectural history. Not to mention, some of the views that I was able to get from that tour I will, quite literally, remember for as long as I live.

There’s probably no 90 minute period during my time in Chicago that has been so carefully crystallized and that I can rewind and play back at will so well. That, to me, is always a sign that it was something special.

It’s the opportunity to contextualize the rest of your Chicago experience while simultaneously getting a taste of the best of the city, and a history that, as far as I’m concerned, only a few cities can rival on the continent.

My guess is, if only have 48 hours in Chicago, it’s during these 90 minutes that you’ll fall in love with the city. I should also add that they run a Twilight River Cruise and Yoga Cruise is that’s more up your alley as well. Whatever boat you take, whatever tour you do, just make a point of getting out on the Chicago River.

As a side-note, this isn’t the only notable throughway associated with Chicago - Route 66 starts from Chicago!

Attending a Chicago Sporting Match

Your Chicago itinerary needs to include a visit to Wrigley Field and a Chicago Cubs baseball game

Even if you’re not a sports fan, the history of the city of Chicago and its sports teams are inseparable, so I’d recommend at least looking into attending a sporting match. It’s going to be dependent on the time of year, but ultimately you’ll be aiming to see the Chicago Bulls, Chicago Cubs, Chicago White Sox, Chicago Fire, or Chicago Blackhawks.

I’m a sports history nut, so my number one choice was to see the Chicago Cubs at Wrigley Field, and that’s exactly what I was able to do. My great friends Devin and Justine (who Bri and I were close to in Turkey, and still are close to now), joined me for the game, but, unfortunately, the Cubs got destroyed by the Athletics.

That being said, we got some beers before and after the game in Wrigleyville, and just to say I’ve been to Wrigley Field is a huge bucket-list item for me.

Whatever your preferred sport, I’d say it’s worth getting to a game. Sports are a way to gauge the pulse of a city, and going to a Cubs game confirmed what I already knew - that Chicago is a passionate and proud city.

People who don’t respect or love sports don’t quite understand that attending a sporting match is likely the quickest way to get a real read on what a city and its people are all about.

If warmer US destinations are your thing, check out my articles on Tempe, Arizona, as well as the 10 Best Family Vacation Spots in Florida

The Skydeck Chicago at Willis Tower

The Skydeck Chicago was worth visiting simply because it’s the tallest building in the Western Hemisphere, and it offers unforgettable views of the city. I mean, you’re not getting this view anywhere else.

“The Ledge” is also a fun experience in that you get to walk out about 4 feet into this glass box over the city, and you’ve got all kinds of butterflies in your chest. It’s 103 floors up, baby!

However, it’s worth being aware of the fact that visiting the Skydeck Chicago can eat up a lot of time on your Chicago itinerary because of the amount of waiting that’s involved during peak times. Sadly, you aren’t the only one who wants to get out onto “The Ledge.”

For reference, I believe when I went people were waiting 45 minutes or so just to get up to the top floor, then another 30 or so minutes if they wanted to do “The Ledge.” It may have been more, but I did go during prime tourism season when kids were out of school, so it’s entirely possible you’ll have better luck, I mostly just want to do my job as a travel writer here in informing you may wait.

I’d avoid going on weekends if you can, and go as soon as it opens if possible (9am March-September and 10am October-February). Especially if you’ve only got two days in Chicago, you need to make sure you think carefully about how to fit this in, so it doesn’t accidentally take up too much of your day. If you do this right, my guess is you can arrive, get up and get down in about 1.5-2 hours or less.

If you can do this quickly and efficiently, then you’re going to get some of the most memorable and exquisite views of the city of Chicago, so really just make sure you’re not going at noon on Saturday in the summer, and you should be good to go.

As a side note, Skydeck E-Tix holders are permitted to early entry at 8:30am on Saturday.

Exploring Chicago’s Wicker Park and Bucktown Neighbourhoods

If you’ve only got two days in Chicago, you should still make an effort to get to the WIcker Park neighbourhood in Chicago!

It seems every city has their neighbourhoods which lie just outside the downtown core (though not too far away), and serve as a refuge for those who actively don’t want to be in the downtown core.

Wicker Park and Bucktown remind me a little bit of Toronto’s Kensington Market in that they’re creative epicentres which are worthy of exploration just to see what the inhabitants of those neighbourhoods are up to.

I had Peter Orlinksky of Chicago Greeter Tour lead me around and show me the live music venues, the architecture that defined both Wicker Park and Bucktown, some neat cafes, a few chef-driven restaurants and just to generally fill me on the history and stories of these respective neighbourhhoods.

We even popped into a bank which had been converted into a pharmacy and had a “piil vault” now. Peter had a passion for the area that was noticeable from the beginning, and he came well prepared with all the info I could ever want to know about Wicker Park and Bucktown.

We also took a walk through the Flat Iron Arts Building, which is a central hub of the Wicker Park neighbourhood. The building is dedicated to providing artists the space to work, as well as showcase their work. You can find everything from visual artists, to costume designers, to tattoo artists, to theatre performers (and performances sometimes), and everything in between.

I’d recommend taking about an hour to walk around Wicker Park and Bucktown and to pop in and out of stores, cafes and so forth, and then another 30 minutes to an hour just to meander around the Flat Iron Arts Building.

I know that time is tight if you’re trying to figure out what to see in Chicago in 2 days but I think it’s important to see these neighbourhoods as a counterpoint to the downtown core, which is where you’ll be spending a bulk of your time.

If you like wine, USA Today just voted the Finger Lakes the best wine region in the US for the second year in a row, and I’ve got an article about the Best Fingers Lakes Wineries.

Millennium Park

You’ve got to see Millennium Park and make sure that as a Chicago trip planner it’s on your list.

Millennium Park is a public park located in “The Loop” area of Chicago, and it’s the top tourist site in Chicago. Believe it or not, with over 25 million annual visitors, it’s actually one of the top ten most visited sites in the entire country.

The first thing that you should do is check the events calendar for Millennium Park during your visit. It’s entirely possible that there’s something great going on while you’ll be here just by virtue of how much is going on in Chicago seemingly all the time.

The main area for events and so forth is the Jay Pritzker Pavilion, a bandshell designed by the world famous Frank Gehry. You’ll know it’s Gehry’s work right away when you see it, as it’s got that striking flowing stainless steel look. It serves as an outdoor performing arts centre, as well as a general hub to meet.

Cloud Gate, also known as “The Bean,” is a three story structure that literally reflects the city and the people who come to see it. It’s a mirror, which makes it ideal for photography. Honestly, I thought that it was going to be one of those sites that was a dud because it was so overhyped, but I had some fun just watching how people interacted with “The Bean,” as well as shooting some photos.

You could spend all day in Millennium Park if you wanted to, but if you’re under time constraints (which you likely are if you’re reading this post), then make sure you see the two spots listed above, then assess whether you’ve got more time to spare.

If you do have some extra time (and it’ll likely be worth it for you to make that time), then go to The Crown Fountain, an interactive video sculpture, as well as the ever pleasant Lurie Garden.

Venture Beyond Just the Signature Dishes

If you’ve only got 48 hours in Chicago, you’ve got to make the most of it and eat, eat, eat.

In truth, I could have eaten only deep dish pizza and Italian beef sandwiches and been happy, but I realize that Chicago’s food scene is about a little more than that. Though, fair warning, if you’re planning your Chicago itinerary for only 2 days, you won’t be able to squeeze in too much room beyond the classics if your goal is to try all the Chicago staples.

In case you do have some extra time, though, or are there longer, I’m going to recommend a few places to grab a bite in Chicago that I felt were pretty tasty and worthwhile.

Lou Mitchell’s - This is an iconic breakfast spot that has been open since 1923, and you really should make an effort to start one your days in Chicago here. It’s classic breakfast fare with the warmest and kindest staff around. In fact, when I entered, I was greeted upon arrival with a donut hole. I mean, that’s just awesome. My mom’s name is also Donna Lu Mitchell, but everyone calls her Lu, so I think that’s probably one reason I love this place even more. How nice of them to name this place after my mom, right?

Revival Food Hall - Revival Food Hall has my love and respect in that it’s a food hall that aims to showcase popular Chicago eateries, as opposed to a normal food hall which might include fast food giants and the like that have nothing to do with the city. I was staying close by, and this was one of my first stops once arriving in Chicago. Looking at what was on offer actually gave me a bit of a cultural understanding of what foods were popular or coveted in Chicago, so it ended up being a good place to start. Here are the current vendors at Revival Food Hall.

Au Cheval - You’re going to have to wait to get into Au Cheval, but if you can manage to get in quickly, or exercise a bit of patience, then you’re going to be dining on what is arguably the best burger in the city. I’m not a big duck fan, but if you love duck, then you should add the foie gras to your burger!

Angelo’s Wine Bar - I don’t think this spot is on enough peoples’ radars in Chicago. It opened originally as a pizzeria in the early 1960s, but has now morphed itself into a top-notch wine bar which features a menu with Midwestern flare, inspired by ideas in cuisine that extend beyond the region. The wine list focuses on boutique wineries from the US, Spain, France, and Italy, and was spectacular. My pal Devin and I went here on a bit of a man date, and we loved it.

The Purple Pig - Going to eat at the Purple Pig isn’t just a meal, it’s an experience. They’ve got an ever changing menu that reflects the ethos of a deeply creative chef, and, appropriately enough, they do pork as well (or better) than anyone in the city. They’ve also got a wine list that’s about 700 hundred bottles deep, so you can feel happy going there for both food and wine.

If you want to see this itinerary in action, check out the permanent highlight on my Instagram page entitled “Chicago” to see my stories on the city.

Go Out on the Town

If you’re trying to tackle Chicago in 2 days, don’t forget to fit some music in.

Any Chicago itinerary is going to be chock-full of daytime activities, but in a city like Chicago, it’s also important to remember that the night offers its own array of cultural experiences. Any good Chicago trip planner needs to include a place or two that only starts to pick up pace once the sun has gone down.

Here are a few spots that I checked out both by myself and with friends that can make for a good night.

Kingston Mines - The legendary Chicago blues scene lives on with this famed Lincoln Park venue, Kingston Mines. They’re open until 4am or later every single night, and the talent you’ll find there is incredible. They’ve got some relatively inexpensive southern style food made to order as well, and plenty of beers on tap. This would probably be my first choice.

Chicago Magic Lounge - This venue for a magic show is probably the best I’ve seen. You enter in through a fake laundry shop, and behind one of the machines is this whole world of magic. Like, literally an entire building, it’s quite something.

I saw the show “Timeless Magic” there, and I have to begrudgingly admit that I wasn’t overly impressed. However, and this is a big however, I talked to folks after the show out front to try to contextualize the performance I saw,, and they said every other show they’d been to had been incredible. The reviews online suggest the exact same thing - so, if you’re going, aim for “The Signature Show,” or another show other than “Timeless Magic.” It’s a memorable night out to be sure!

Sluggers - Located in Wrigleyville, I got a serious kick out of this place. One moment, I’m hitting baseballs in the batting cafe, and the next I’m ordering drinks and listening to two masterful pianists on the duelling piano. This place is just plain fun.

Green Mill Cocktail Lounge - Drink where Al Capone once did! This place even still has the old underground pathways that Capone and his gang used to use to move booze. More than that, they still do Jazz like back in the day.

Logan Arcade - An arcade lover’s arcade bar, this place has a real variety of games on offer, and a beer selection that I wouldn’t have expected. They’ve got craft beers that represent the best of many brewers in the city, state, and country.

Buddy Guy’s Legends - This spot was opened by none other than Buddy Guy in the late 80s and it’s still going stronger than ever. Apparently he still makes appearances on stage with some regularity, and this is known as perhaps the spot for celebrity sightings when it comes to the blues and jazz scene in Chicago. The cajun style food is also all kinds of delicious.

If You’ve Only Got Two Days in Chicago, is a Chicago CityPASS worth it?

Make the most of your 2 days in Chicago by considering getting a Chicago CityPass!

In short, the answer to this question is going to depend on what you value in terms of Chicago attractions. The Chicago CityPass is useful and cost effective only if your goal is to see the 5 most popular Chicago attractions.

What I did was research what I wanted to make sure that I saw while in Chicago, then looked at what was included in the Chicago CityPASS. So what is included?

  1. Priority entry to the Shedd Aquarium

  2. Day or night entry to the Skydeck Chicago

  3. An all access pass to the Field Museum

  4. Entry, 2 shows,and the Atwood Sphere Experience at the Adler Planetarium OR a fast pass to the Art Institute of Chicago

  5. Entry plus 1 ticketed experience at the Museum of Science and Industry OR express entry to the 360 Chicago Observation Deck.

Your CityPASS is valid for 9 days, and at a price of $108, if you tackled all of these attractions, it would save you about 50% of the normal cost.

However, for me, if I had just 48 hours in Chicago, I’d want to prioritize the Skydeck Chicago, as well as Art Institute of Chicago, then get a feel for neighbourhoods, sporting matches, and restaurants, so it likely wouldn’t be worth it for me personally.

The best thing to do, as I said, is think about what your Chicago itinerary would include, and if many of the above sites are on your list, then a Chicago CItyPASS is going to make a lot of sense for you.

Where to Stay in Chicago?

If you follow the path I’ve outlaid here to explore Chicago, then it’s going to make sense to be centrally located, but you’ve got some options. I’d personally say to stay in The Loop, South Loop, Streeterville, River North, West Town, or West Loop if you want to be in the heart of the action. If you want something a little different, then Wicker Park or Bucktown might be more your style.

Now, I’ll be up front. the hotel that I stayed in was located perfectly in the downtown core on West Adams Street, and it was spectacular by any standard. I was staying in the JW Marriott Chicago, and it’s a landmark Chicago hotel.

Beyond being in the ideal location, the JW Marriott Chicago had an impressive full-service spa, indoor pool, modern fitness centre and fine dining options. The Burnham Ballroom was also exquisite and spoke to the impressive past of the hotel. I was within walking distance of most of what I wanted to see, so I loved it there. Though, this level of luxury and location won’t come cheap, but that’s to be expected with a hotel of this caliber.

You can see if it’s right for you, or just explore what else is on offer in Chicago below.

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Is 48 Hours in Chicago Going to be Enough?

Here’s the thing - you can see and do a lot with 48 hours in Chicago, but obviously it’s a city that you’re going to want to spend as much time in as you can in. As a travel writer I hate to use this cliché phrase, but it really is like no other city, and that means that two days in Chicago probably isn’t going to be quite enough time, but it isn’t nothing either. Hey, if you’ve only got two days, that’s what you’ve got.

In Chicago, there’s this feeling of a booming metropolis not unlike New York City, but instead of being treated with a hurried indifference as can happen in NYC, Chicago is quite approachable and welcoming. It sort of felt like a whole bunch of people from a small town decided to start a big city - I instantly understood why everyone talks about how pleasant the Midwest can be.

Even just doing your best to see Chicago in 48 hours, you’ll get that feeling, and understand what Chicago is all about.

Coming to Chicago, my expectations were through the roof, and I left the city feeling that my expectations were more than met. I left the city wondering if Chicago might now be my favourite city in North America.

I want to humbly thank Choose Chicago for hosting me as media. All opinions are completely my own. Below, I’d love to know in the comments if you’ve visited Chicago before and your thoughts! I respond to each and every comment.

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