2 Days in Chicago – A JAM PACKED Itinerary!

If you love big city travel, then Chicago needs to be on the top of your bucket list! This bustling big city is filled with history, jaw-dropping architecture, world-famous restaurants, and epic events. If you only have 2 days in Chicago, you have to fill every second with activities! Okay, maybe not EVERY second, but if you know my travel style at all, you know it will be jam-packed so you can see as much as possible!

Speaking of events, I originally traveled to Chicago for their annual St. Patrick’s Day festivities, which is one of the best cities in the world to be for that holiday. They die the river green, parades fill the streets, and the bars throw epic parties! Because of the COVID-19 pandemic, they cancelled everything the day before we were scheduled to travel out! Because things took a big downturn throughout the weekend we were there (which is VERY scary to be away from home when sh*t hits the fan!), everything was closing down while we were there.

Normally, I only recommend things that I have personally tested out, but this itinerary will be a little different! I WANTED to try out a lot of stuff, but because things were closed, I found alternatives. I will list both the things I would have done if things were open AND the alternatives I chose.

Even though this guide is for 48 hours in Chicago, I added a bonus section at the bottom in case you want to spend another day or two in the city. I also listed out the best area to stay in, what to pack and best time of year to go! Okay, let’s dive in!

There is a chance that this guide contains affiliate links. This means I might make a small commission (at no extra cost to you), that goes directly towards little Rosie’s dog treats! 

Best area to stay in Chicago

There are a lot of areas of Chicago that are not safe, especially for female travelers. You will want to make sure you do your research on the best and safest areas to stay in to avoid any hiccups during your trip!

A lot of my family and friends are from Chicago, so I asked the local’s where the best area is! I am not exaggerating when I say ALL of them said River North is by far the best area to stay in. Not only is it a safe area, but this is where all the best bars / restaurants are located and it’s extremely central so you can easily walk to all the sights. Uber/Lyft can be quite expensive in a big city because of the traffic, so it will end up saving you a lot of money if you are able to walk to most places.

Here are the best picks in the River North area by budget:

$: Homewood Suites by Hilton

$$: ALoft Chicago Downtown River North

$$$: The Peninsula Chicago 

TIP: If you are traveling with a group, definitely check out Airbnb! There are extremely nice multi-bedroom condos that you can rent for your 2 days in Chicago. If it’s your first time using Airbnb, click here for a discount code! 🙂

Best time of year to travel to Chicago

One of the best cities in the world to celebrate St. Patrick’s Day is Chicago, so my easy answer is: During St. Patrick’s Day weekend! They dye the entire river green, parades fill the streets (not kid parades, ones where they pull everyone onto the floats to take shots kinda parades!), and the bars throw epic parties with green drinks! This is when I went, but unfortunately due to the COVID-19 outbreak, everything was cancelled the day before we arrived 🙁

Don’t worry though, I will DEFINITELY be back to experience Chicago is all its St. Patrick’s Day glory!

If you hate crowds, or don’t want to spend a fortune going during a holiday weekend, I would recommend summertime! It is no secret that Chicago is COLD AF. Even in the “spring” time, you will likely see snow on the weather forecast. If you want to explore the city by foot, take a boat ride, hang out by the lake, and enjoy the rooftop bars, then middle of summer will definitely be best.

What to pack for Chicago

If you are traveling to Chicago for St. Patty’s day weekend, then make sure you deck yourself out in St. Patrick’s Day decor! Even though all the formal events were cancelled when I went, everyone was still head-to-toe in green and had clover face tattoos! Chicago locals have NO SHAME!

For a regular weekend in Chicago, I would definitely still bring warm clothes. Even if the weather doesn’t seem to be cold on the forecast, the wind can make it feel 20 degrees colder. Here are my top must-haves:

1. Hot Hand Hand Warmers

Guys, you need to trust me on this one. I am not kidding you when I say these SAVE MY LIFE every time I travel to a cold destination. I purchase an entire box of these on Amazon and stick a new pack in my gloves every day. I’ve brought these on my trips to NYC in the winter, Banff Dog Sledding, and this trip too! Click here to snag some.

2. CC beanies

If your head isn’t warm, you won’t be warm.. It’s as simple as that. I bought a few pairs of these beanies on Amazon a few years ago and have taken them on all my trips with me (CC Beanies are the BEST)! They’ve lasted forever and come in a million different colors. Click here to check them out!

3. Chicago CitiPass

Okay, you don’t technically pack this, but you should definitely look into buying this before you go! CitiPass is a company that bundles a cities popular attractions so you can save money. If you plan to do more than one of the things on this Chicago itinerary, I would DEFINITELY buy this pass!

P.S. This beanie is from Urban Outfitters, Sweater is from Lulu’s, and Jeans are from Madewell! 🙂

2 Day Chicago Itinerary

If you only have 2 days in Chicago, you need to use your time wisely! There is a ton of stuff to see in this bustling city, so I grouped everything by location so you don’t waste a lot of time driving. Day 1 will be centered around the touristy sites like Millennium Park and Navy Pier while Day 2 will be in the River North area. The things listed on these 2 days are what I would recommend, but I also added a bonus section at the bottom if you want to squeeze a few more things in. Here we go…

Day 1

Morning:

Start your morning off with some sightseeing to catch that great lighting and minimal crowds! Chicago is a big party town, so if you wake up early to do the sightseeing, you will beat most of the crowds. First stop, Cloud Gate (AKA The Bean), is easily the most popular attraction in Chicago! Why? I’m honestly not sure. It is such a weird, quirky thing to get people to travel to a city, but hey! It worked because I wanted to see it! 🙂

The pictures do not do the size justice, you’ll be amazed by how HUGE this thing is!

Cloud Gate / The Bean is located in Millennium Park, which is a surprisingly huge area. If the weather is nice, I encourage you to stroll around the area to see the large fountains, sculptures and great views of the city!

If you want an even better view of the city, head over to Adler Planetarium to enjoy the best view of the Chicago Skyline. There is a large grass area right on the water that overlooks the city, so make sure you pack a picnic lunch on a nice day to enjoy here. I did not have time to go to Adler Planetarium, but many local’s recommended this spot for the best view of the skyline!

And a bonus.. it is a total local’s spot! You won’t be sharing this area with crowds of tourists fighting for the perfect Instagram shot.

Afternoon:

Also in this area is Navy Pier where you will see the staple of the large Ferris wheel! You could easily spend an hour strolling along the pier, souvenir shopping and taking pictures in front of the massive wheel.

Next up, you can’t go to Chicago without having a deep dish pizza! I turned to the local’s on this topic because apparently it’s still a running debate on which place has the best pizza. Majority of the local’s said that Lou Malnati’s is the best, and after trying it, I can definitely agree! Guys, the butter crust pizza is UNREAL. 

Also, I am fully aware of how AWFUL this photo is, but I swear it tastes better than it looks lol. This is why I am not a food blogger people!! 🙂

Evening:

The best spot in town for sunset views is Cindy’s rooftop bar, located in the same area as Millennium Park / The Bean! There might be a wait to get to the top, but I promise the views will be well worth it. All of the rooftop bars were my favorite thing about Chicago, well, any big city!

To end the night, I would recommend bar hopping throughout River North (which is where I recommended you staying). Make sure you check out Howl at the Moon Piano Bar, which is the best bar EVER! It is lively, fairly priced and has amazing entertainment!

Bar hopping not your thing? Or traveling with your family? Check out this guide on Things to do in Chicago with kids instead!

Day 2

Morning:

This was one of my favorite experiences in Chicago, and it was an unexpected, last minute thing! The largest Starbucks Reserve in the world is located in Chicago and MAN is it cool. There are 5 levels to explore where you can try homemade pastries, espresso flights, unique lattes, and the best part.. Espresso Martinis!!

Have you ever seen such a beautiful site? 

Afternoon:

There are two tourist spots in Chicago that give you amazing views of the city: First is The Skydeck and second is 360 Chicago. If I had to choose, I would choose The Skydeck because they have glass pop outs for amazing views and photo opps! Because I traveled to Chicago during the COVID-19 outbreak, the city was literally closing down while I was there and The Skydeck was closed.

360 Chicago was still open and was still really great! They have a cool attraction where you can lean against a glass wall, and the glass wall will extend out so you feel like you are flying over the city – really gets the palms sweating! Either one you choose, they both give you great views and are around the same price!

TIP: If you plan on doing two or more tourist attractions in Chicago, you will end up saving money by buying the CitiPass because it gives you a bundle deal! 

If you are going during the summer months, I would also recommend doing an Architecture Tour! This was easily the #1 recommended thing in Chicago by all my local friends. You hop on a boat and cruise down the Chicago River for 1.5 hours learning all about the city’s unique history! Tickets cost around $50.00 and the tour only runs during the summer (because Chicago is cold AF and the river is frozen most of the year haha). Click here to read more about it!

Evening:

Stroll along the scenic Michigan Ave until you reach London House, which is another amazing rooftop bar with incredible views! They have an indoor and outdoor section, making it the perfect spot to enjoy your sunset cocktail.

After your cocktails with a view, either go out to a nice dinner or go bar hopping in River North again. If you didn’t make it to Howl at the Moon Piano Bar on night one, make sure you go. It’s a MUST!

BONUS things to do:

• Go to the Art Institute of Chicago – This is included on that CitiPass thing I mentioned! This is one of the largest and oldest museums in the USA, home to famous pieces of art from Pablo Picasso, Vincent Van Gogh, Andy Warhol, and more!
• See a baseball game at Wrigley Field – Late March to Early October is baseball season for those of you who don’t know (me… I don’t know. I had to Google that for you HA).
• Lounge at one of the many beaches – Montrose Beach, North Ave Beach, Oak Street Beach, Ohio Street Beach, Etc.
• Go shopping along Magnificent Mile, a luxurious section of Michigan Ave, where you can shop at big-name places like Norsdrom, Macy’s, Bloomingdales, and more!
• See the amazing architecture of Holy Name Cathedral, which is completely free to explore!
• Go to Garfield Park Conservatory to see the gigantic botanical garden. Even though this is a ways away from the touristy sites, the pictures of this place look amazing!

Food Must-Try’s:

So, the only reason my man loves to travel is to try all the cities best food spots! So you already know he did extensive research and asked all his local friends for recommendations. We tried to squeeze as many eating and drinking activities that we could during our 48 hours in Chicago, and here is the final list:

• Au Cheval’s Burgers – People swear this is the best burger in the world and will always have a line wrapped around the block. Because of COVID-19, they were closed while we were there so we didn’t get to try it. I wish you guys could’ve seen the TANTRUM my boyfriend, Joseph, threw when we walked up to that door and it was closed LOL.
• Portillo’s Hot Dogs – Where you can get a famous “Chicago Dog” that has a ridiculous amount of toppings on it.
• Lou Malnati’s Deep Dish Pizza – I mentioned this above, but make sure you get the butter crust!
• Ramen San – BEST RAMEN EVER. So nice if you are traveling when it is cold outside!
• Duck Duck Goat – Yummy Asian food!
• Walton Street has a tasty bottomless mimosa brunch.

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Okay, that’s a wrap! Even though half of Chicago was on lock down while we were there, we still had an amazing time! I can’t wait to go back and explore this exciting city once it is open and bustling. These 2 days in Chicago will be jam-packed to say the least, but at least you will get to maximize that flight ticket!

Like this guide? Here are some other big-city guides I think you would love!

• 48 Hours in NYC
• Couple’s Guide to NYC
• Instagrammable Spots in NYC
• Unique Things to do in San Francisco

Thanks so much for stopping by! 🙂

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