A Perfect Weekend in Chicago: Your 48-Hour Itinerary
It’s safe to say Chicago is one of those cities that once you go for the first time you truly fall in love with it. Honestly, if it didnt get SO COLD in the winter I could lowkey see myself living there.. But yall know me- I DON’T DO THE COLD LMAO so it would literally never work. Still, she’s super cute and a great place to travel 🙂 I actually just got back from a weekend trip not too long ago with my friend and we had a BLAST. I don’t what it is about this city, but Chicago just hits different! I think it’s probably because it has the perfect blend of architecture, night life, history and a FIREEE food scene. Which makes it the ideal place to visit! So whether it’s your first time, or you’re spinning the block take a quick look at this weekend itinerary before you touch down.
Day One (Friday)
Yes. This may be your travel day… but rule number 1 for weekend trips? The vibes start AS SOON as you arrive. THAT’S LAW! So, if you get there in the evening, head straight to your hotel, freshen up, and get ready for a chill but fun night out in one of Chicago’s most lively neighborhoods—Fulton Market District!
I loveeeee FMD because they have something to do for literally whatever mood you’re in. Chill, aestheticy bars/lounges, upscale restaurants, tacos, burgers, a really yummy cookie spot and a few fun clubs if you’re into that too. My recommendations?
If you’re feeling a bit boujie and want something kinda fancy go to The Aviary- its a cute little cocktail bar and it’s the perfect place to create some scroll stopping content.
If you’re looking for some good eats, head over to Roister! They’ve got really good food options and a much more chill atmosphere.
Whatever you do, don’t feel too pressed! You can literally walk around and feel out the vibes at your own pace- there’s a whole weekend ahead.
Day Two (Saturday)
Pleaseee don’t tell me you’re one of those people who come on a vacation and want to sleep in until noon? Bc we could never travel together if you are lol. I’m very much the friend who wants to be out and about by 930-10! Even if we just start off at a cute cafe or breakfast spot, we’re getting up and out of the room… ESPECIALLY if we are on a weekend trip. Time is of the essence in case you forgot hahaha.
So for our one and only full day, we’re hitting the streets hard. Grab a quick bite or your fav latte so you can have something on your stomach and get ready to start your day with hands down one of the BEST ways to see the city- a boat tour on the Chicago river! With tickets being less than $30, this is a MUST do activity when in the city. You’ll take a 90-minute guided tour on a huge boat (that has a bar on the bottom deck, btw), as you learn about the city’s iconic history and get lost in the mesmerizing postcard-worthy views of Chicago’s downtown skyline.
My suggestion? Book through viator using this link and opt into one of the early morning time slots so you can beat the crowds!!
Once you’re done soaking up all the architectural knowledge you can, it’s time to eat (i knowww you’re hungry lol). Now, who the hell comes to Chicago without getting some deep dish pizza?… No one- EXACTLY and you will not be the one person that does.
Just a few blocks down (totally walkable distance, btw), you’ll find Lou Malnati’s! One of Chicago’s OG spots for a good deep dish, and I promise you will not be disappointed. They’ve got some of the best cheesy, buttery, sauce-covered pizza’s you’ll probably ever have so if this wasn’t on your itinerary already.. Add it now!
At this point, it’s probably around 2 or 3pm and even though you might be feeling stuffed and ready to lay down (i get this itis after eating a piece of gum so trust me.. I get it), but don’t go home yet!! While you’re in the area, you’ve gotta go see Chicago’s most famous landmark- The Bean! It’s located in Millennium Park, which is only about a mile or so away from Lou Malnatati’s so you’ve got the perfect opportunity to walk off that food before heading home for a (SMALL) rest period.
FULL TRANSPARENCY- I’m not really a night girl hahaha, I get up around 6am and am literally ready to conquer the day within an hour of opening my eyes so evenings for me on trips like this usually look like binging a few movies and maybe ordering some doordash from a local spot while I edit the content I filled my camera roll with throughout the duration of the day. BUT! If you like to go out, I think you should do that… don’t be like me lol im a granny. Get dressed, get cute, and hit the town because there’s truly SO much to see 🙂
Sunday (Day Three)
You know what’s better than your average Starbucks..? A Starbucks with five floors and a rooftop!!! C’mon now… at this point we’re practically besties so I already know what youre thinking. “What does Starbucks possibly need five floors for?” I thought the sameee thing actually but once I stepped foot through those doors I instantly understood lol.
Long story short, this strarbucks mansion a.k.a Starbucks Reserve is easily any coffee lovers paradise. They have exclusive coffees, pastries, a bar, different interactive stations where you can have a quick history lesson or two, lots of seating areas and again.. A daggon rooftop for you to enjoy your coffee with a view- it’s crazy!!! Literally one of those things you’ve just gotta see with your own two eyes to understand so while in Chicago make sure you hit up Michigan Ave so you can take a peek!
I hope you didn’t think we were about to leave Chicago without a little bit of retail therapy? Especialllly after you’re already on what’s known as the “Magnificent Mile”!! This is Michigan Ave’s strip of the best stores, from designer to department- whatever you’re looking for you’ll probably find it here. So, walk around a little and let go of the tight grip you have on your credit card because it’s time to buy yourself something nice before you head home!!
And just like that…
You’ll quickly see upon your arrival, a weekend in Chicago is NOTHING. I mean, even with our jam packed weekend we still barely got our feet wet! But, I hope I gave you a great visual representation of what to expect when you go on your own. Just remember there’s ALWAYS something to explore here, so don’t feel like you have to rush to get everything done in one trip. Pick a few of the best experiences (whichhhh, i’m not saying are these but…) and be present while you enjoy them. As always, safe travels and let me know what you think if you do any of the things we talked about above.
Xoxo,
Dru <3