After weeks and weeks of overtime work and frozen dinners, you finally got your paycheck. But instead of putting it into your savings account like the responsible adult you should be, you decided to book a spontaneous weekend trip to Chicago. So now what? How do you know what the best things to do in Chicago are? Do you go and purchase Chicago travel guides from the local bookstore? Do you google Chicago trip planners? Or are you already pulling all your hairs out because the Type A personality in you forgot how stressful last-minute trip planning is?
Well, hakuna matata because you’ve come to the right place. Without further ado, here is your ultimate 48-hour Chicago itinerary for a perfect weekend in Windy City.
1. Check-in at a boutique hotel.
Check availabilities here.
In “The Alise Chicago – A Staypineapple Hotel [Review]“, I was raving about the cutest and most considerate boutique hotel in the Chicago Loop area. Not only is The Alise centrally located and within walking distance to Millennium Park, they absolutely go above and beyond to make sure guests have the most enjoyable stay. European style duvet. Comfy hotel slippers. Central charging station. Super turbo strength blow dryer. Unlimited drinking water. You name it! Oh! And it’s also housed in a historic building. Experience quality stay AND get a taste of Chicago’s history. Talk about killing two birds with one stone!
Daily complimentary coffee and cupcakes from 3:30PM to 6:30PM.
2. Get lit! Hit up Chicago’s most popular rooftop bars!!!
So you’ve had a long flight perhaps. Maybe you ate on the plane, maybe you didn’t. In the case that you are famished after check-in, here are some of the city’s best restaurants for pre-game. Better yet you could just opt to dine at some of Chicago’s well-known rooftop bars & lounges!
Photo from London House Chicago.
Having appeared in popular online guides from TimeOut and Thrillist, LH Rooftop at London House Chicago is no doubt an absolute gem. It is located on the 21st (indoor) and 22nd (outdoor) floors and offers panoramic views overlooking Chicago River and Michigan Avenue. Although more on the expensive and luxurious side, it’s certainly quite the experience sipping on a glass of bubbly here.
Yet another panoramic type establishment, but who can get sick of them!? Cindy’s provides unparallel views of Millennium Park and Lake Michigan and did I say their food menu is droolicious? They are known for their massive portions too – great for sharing with friends. Now that’s how you kickoff a weekend in Chicago! 😉
3. Start the next day with a cup of hot chocolate from Nutella Café.
NUTELLA CAFÉ!? Yes! You read that right!!!!! I had no idea this magical place even existed until I was looking up things to do in Chicago. This is actually the first ever Nutella café and has only opened recently in May. Definitely a must for all you Nutella lovers out there.
My friend ordered the crêpe, which she found to be nothing special. I do recommend the Seasonal Fruit Hand Pie however. The pastry dough had a nice flaky crust and the blueberries were a little tart but paired with the sweetness of the hazelnut Nutella sauce drizzled on top, it was divine perfection.
Their menu includes a hot chocolate/cocoa. Ask the server for their special Nutella edition!
4. Stroll the Chicago Riverwalk.
Literally only a few seconds away from the Nutella Café, the Chicago Riverwalk is a nice area for enjoying your hot Nutella drink. (Or maybe cold if you’re visiting in summer.)
Real Fake sculpture by Scott Reeder in front of Trump Tower.
On a good day, you can see the beautiful turquoise color of Chicago River glistening in the sun. Victoria from A Traveling Translator commented on my previous Chicago post to let me know that the river is actually dyed completely green on Saint Patrick’s Day. Surely that’s a sight not to be missed!!!
For those that don’t care much for the night life, do still check out LH Rooftop when you’re in the Riverwalk neighborhood. We easily took the elevator from the hotel lobby up to the 21st floor then walked a few flights of stairs to the 22nd outdoor terrace. Even though the lounge was technically closed during the day, a security guard saw us but did not say anything. I’m assuming it’s allowed? If not, this could be our little secret, shh!
The elevated city view was simply spectacular. Such a shame the weather didn’t co-operate with us because I can’t begin to imagine how much more incredible this scene would’ve been on a sunnier day. Highly recommended!
Looking for free things to do? Give this Chicago rooftop guide a read.
5. Take a reflection selfie at Cloud Gate, Millennium Park.
Ahhhhhhh yessssssss. The giant jellybean! This is probably on everyone’s what to see in Chicago bucket list. How can we forget about this Chicago icon!
I don’t know why but after seeing photos online, I pictured it to be gigantic. It turned out quite a bit smaller in person, but still quite a fun photo op location.
Cloud Gate was created by Indian-born British artist Anish Kapoor. It was a submission piece for a design competition in which he was inspired by liquid mercury. The sculpture is made of stainless steel plates and there are no visible seams. Although questions and concerns were raised during the initial implementation phase of this project, the bean has since gained local popularity and international fame.
Cloud Gate at night is quite lovely as well. Also don’t forget about the Crown Fountain while you’re at Millennium Park!
6. Hunt down Chicago’s IG-famous murals.
What I love about a mural is that it transforms a simple, blank space into the canvas of a creative mind.
Again, my trip took place during a colder, rainier month hence I didn’t spend much time outdoors. The Muddy Waters mural was seen from my room at The Alise. The other two I spotted on my way back from brunch from The Allis @ London House to the Chicago L Pink Line station in the Fulton Market District neighborhood. Don’t have the exact addresses but these two were definite showstoppers. Below are other murals I recommend seeing and ones I’m excited to check off my bucket list for my return visit.
Greetings from Chicago
Photo from Style Charade.
Address: 2236 N. Milwaukee Ave, Chicago, IL 60647
By the talented Victor Ving and Lisa Beggs, this mural pretty much sums up Chicago. Here is what each of the letter depicts:
- C – deep dish pizza & Chicago style hot dog
- H – Gold Coast/Downtown skyline
- I – the Chicago flag & Illinois Centennial Monument in Logan Square
- C – abstract artwork by Amuse126 depicting the extremes of Chicago weather
- A – Chicago’s professional sports teams
- G – Muddy Waters & Ferris Bueller’s Day Off Water Tower
- O – Cloud Gate beach sculpture
The Flamingo Rum Club
Photo from Seb Dona.
Address: 601 N Wells St, Chicago, IL 60654
Despite having seen several Instagram photos of this insanely cute flamingo mural, I didn’t find out it was actually located in Chicago until after I got back home. The Flamingo Rum Club is a Cuban restaurant and rum bar. Their interior is absolutely darling as well although there are some mixed reviews.
Wabash Arts Corridor
“Moose Bubblegum Bubble” by Jacob Watts. Photo from WAC.
Address: 33 E. Congress, Chicago, Il 60605
In 2013, Columbia College Chicago launched the Wabash Arts Corridor project to encourage students to get in touch with their creative side to transform and beautify the South Loop business district. According to their official webpage, “The Wabash Arts Corridor is Chicago’s living urban canvas that connects the visual, performing and media arts.” Jacob Watts’ bubblegum mural is only one of the many student projects commissioned by WAC. Here is a complete list of their artwork.
7. Enjoy sunset at Willis Tower’s Skydeck Chicago.
My “6 Chicago Tourist Traps to Avoid” post revealed that Skydeck is not worth the money. I am, however, putting this on the list because it is an exceptional experience for those who have never been to a glass-bottom, see-through observatory deck. Just be prepared for long lines and note that you also only get a few seconds on the actual balcony. (There are four queues in total. No time limit for the rest of the observatory.) If you have a DSLR, make sure you set your settings right for back-lit photography.
8. Laugh out loud at Saturday Night Live.
Photos from Time Out Chicago.
Okay, maybe I’m not really talking about attending the show here…
On October 21st, Chicago introduced a Saturday Night Live: The Experience exhibition that showcases all the behind the scenes top secrets of this three-decade-old TV legend. The exhibit is structured as a week in the life of SNL. You’ll see how the TV events come together each week with Monday being a meeting with the guest host, Tuesday the writing session, Wednesday the table read, and so on all the way up to Saturday’s live performance. From costumes and set pieces to original scripts and artifacts, you get to experience what it’s like running this classic American production first hand.
Please note that this is a traveling tour and is set to run for 14 months in Chicago. Tickets are $25 so if you’re a fan, be sure to plan accordingly for your Chicago getaway.
9. Rise and shine! Brunch at The Allis Soho House.
It’s the last day of your weekend in Chicago. Let’s get some food in you and start the morning right.
I had the pleasure of dining at The Allis thanks to the Soho House team’s kind and hospitable invitation. My girlfriend and I definitely ordered a little too much but everything on the menu looked to die for!
Smoked Salmon Bagel.
I must say the food was phenomenal. The Smoked Salmon Bagel, in particular, was absolutely delightful. I liked how they didn’t assemble it and you could add how ever many slices of salmon or tomato you wanted. Super cute dining space too perfect for a casual girls date or even business meetings and group celebrations. No wonder it’s featured as an Instagrammable spot in so many online blogs!
10. Frolic down flower paths at Garfield Park Conservatory.
Silly me put this on my “places to see in Chicago” list and completely forgot about it due to my gold fish memory. Guess I got one more reason to return now!
The conservatory is often referred to as “landscape art under glass” and occupies approximately two acres of land with an additional 12 acres of outdoor gardens. Their mission is to educate and inspire visitors through innovative programs and botanic experiences.. Admission is based on suggested donation.
By the way, if you’ve watched the classic Vince Vaughn and Kevin James movie – The Dilemma, you might even recognize the Fern Room where Ronny planned on proposing to Beth.
Ready for your Chicago trip? Book a hotel today!
And there you have it! Your perfect Chicago trip planner!
I’ve mainly included Chicago activities that I personally found worthwhile as opposed to the typical, popular tourist destinations (e,g, The Tilt at 360 Chicago, Giordano’s deep dish pizza, etc.). There’s obviously so much more you can do and countless things to see in Chicago that one weekend probably isn’t enough for it all.
Also keep in mind that depending on the season of your visit, Chicago may or may not have a lot going on. I say that coming from experience, as my trip took place during Remembrance Day (Veterans Day in the U.S.) long weekend in November. It was far too cold for outdoorsy activities (e.g. boat rides or rooftop bars) and a lot of the famous fountains were closed (Crown Fountain and Buckingham Fountain). That said, this Chicago trip planner is aimed at helping you narrow it down to the top things to do in Chicago given a 48-hourish time frame from Friday night to Sunday afternoon. Hopefully you guys will enjoy this guide and find it helpful!
PS. still looking for a camera upgrade. Seems like I’d prefer a full-frame over the mirrorless Fujifilm X-Pro 2 that I currently own. If you have any recommendations, comment down below 😀