Here’s How I Spent 48 Hours In Chicago

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For the amount of travel I’ve done as both a child and an adult, I have shockingly never been to Chicago before – that is until last summer. I was headed to South Carolina for a girls trip, and since there were zero direct flights to Charleston – I decided to make a quick pit stop in the Windy City to finally explore this jewel of the midwest and to also visit a good friend who recently moved back to Illinois. Keep reading to discover what I did during my 2-day-trip to Chicago.

Prior to leaving Los Angeles, I sent my friend a list of the THINGS THAT I REALLY WANTED TO DO during my first trip to Chicago and that anything beyond those activities would just be an added bonus since my time in town was so limited.

MY WISH LIST

SPOT THE SEARS TOWER – I didn’t need to go up. I just wanted to see this iconic skyscraper and once tallest building in the world! I feel like I know my fair share of trivia, but this LA girl was completely unaware that the Sears Tower was renamed the Willis Tower back in 2009 until visiting their website last year…just a fun fact for anyone who cares and/or didn’t already know this 😉
GO ON A RIVER TOUR – In my humble opinion, nothing conveys Chicago better than the waterway that flows through downtown. It has always been a dream of mine to cruise down the Chicago river, stare up at the buildings, and learn the history of this beloved, American metropolis.
VISIT LAKE MICHIGAN – When you’re near one of America’s Great Lakes, you simply have to see it! I’ve seen both Lake Ontario and Lake Eerie during childhood trips to Niagara Falls and Toronto so adding Lake Michigan to this list was a no brainer.
EAT A HOT DOG – I have always wanted to try a Chicago-style hot dog, and this trip was finally my moment to get a taste of this famous, midwest staple.

DAY 1 TIMELINE

2:45 PM – Land in Chicago
3:00 PM – Get picked up from O’Hare International Airport by my friend
3:15 PM – See the Sears Tower from the car during our drive home ✓ CHECK ✓
4:00 PM – Settle in at my friend’s place in North Center
5:30 PM – Head to dinner at Time Out Market in the West Loop [ Bonus Activity ]
7:30 PM – Drive back home to drop off the car & relax for a bit
8:45 PM – Uber on over to DryHop Brewers in Lake View East to enjoy some local craft beer with my friend’s brother & sister-in-law [ Bonus Activity ]
10:00 PM – Another round or two + a late night snack on the rooftop bar of Old Crow Smokehouse in Wrigleyville [ Bonus Activity ]
MIDNIGHT – Head to bed

DAY 2 TIMELINE

MORNING – Wake up late to ensure that I wasn’t sleep deprived / coffee & breakfast at my friend’s place / shower & get ready for the day
12:30 PM – Visit Lake Michigan. ✓ CHECK ✓
My friend took me and his dog to Montrose Beach. It was so lovely to walk along the shoreline and dip my toes into this beautiful, body of water!
2:00 PM – Pick up lunch from Portillo’s, one of the most famous hot dog joints in town. ✓ CHECK ✓
Please don’t be upset with me Chicagoans, but if I had to describe your classic, hot dog – I’d have to say that it was alright at best. Once again, this is just the opinion of a girl who prefers brown mustard, raw onions, and a dash of relish on her dogs with maybe a hint of mayo and ketchup from time to time. A good chili, cheese dog ranks high for me as well. And I can never say no to a 2am bacon wrapped wiener with grilled onions, grilled bell peppers, and a drizzle of mayo, mustard, and hint of ketchup aka the LA Street Dog. Maybe I’m just not a fan of Portillo’s which apparently has two SoCal locations. Maybe I just need to find a tiny mom & pop, hot dog vendor the next time I’m in Chicago since some of the best food is often found at hole-in-the-wall eateries and street carts. That could be the solution! Any suggestions for my next visit?
3:30 PM – Ride the “L” Train from North Center into downtown [ Bonus Activity ]
4:00 PM – Walk amongst the high-rises of Chicago’s shopping & financial district [ Bonus Activity ]
4:30 PM – Visit Cloud Gate aka The Bean [ Bonus Activity ]
5:15 PM – Enjoy a cocktail along the Riverwalk [ Bonus Activity ]
6:30 PM – Embark on a Chicago river tour ✓ CHECK ✓
Once my friend confirmed that he was down to join me on the river tour, I started researching companies. After weighing my options for a few days, I settled on the 90-Minute Architecture boat ride with Wendella Tours & Cruises. I ended up being so incredibly happy with the decision I made because our tour guide was fabulous. He shared the history of the city, the history of the river, and the architectural details of the endless buildings soaring high above with both ease and expertise. But what made this history lesson so perfect was our tour guide’s wit, sense of humor, and fun loving personality. If you’re looking for a good time, good views, plenty of laughs, and a truly educational experience – please book with Wendella. This river cruise was by far the highlight of my trip to Chicago!! They offer multiple tours throughout the day so it’s easy to book one of their experiences that fits both your schedule and your personal taste. Helpful Tips: 1. Purchase your tickets online and in advance. 2. If you enjoy the colors of the setting sun along the water and lit up skyscrapers, I highly suggest you select a departure time that coincides with that day’s sunset. I specifically booked our tour for 6:30pm so we could view the buildings, river, and skyline with the sun up, during sunset, and at sundown. 3. Get in line at least 25 minutes before your departure time if you’d like a seat close to the tour guide. 4. There are both restrooms and a full bar on board. 5. You will have stellar views of the Sears Tower & all of the other historic buildings that line both sides of the Chicago River.
9:00 PM – Late night dinner at Fancy Plants Kitchen in Lincoln Park [ Bonus Activity ]
MIDNIGHT – Start winding down for bed

DAY 3 TIMELINE

MORNING – Wake up / coffee & breakfast at my friend’s place / shower / get ready / pack
My original plan was to grab brunch before heading to Charleston, but I was forced to figure out travel details because United cancelled my flight the night before at 9:30 PM due to pending thunder storms. Their customer service staff was unable to get me on a daytime flight to South Carolina after ages on the phone with them. Fortunately, I was able to find a direct flight from Midway to Charleston via Southwest that left an hour after my originally scheduled trip.
NOON – Head to Midway International Airport
My friend was kind enough to drive me!
1:10 PM – Leave Chicago for Charleston
The plane was full of folks from three different United flights that were cancelled that weekend. Despite the immense hassle, United was kind enough to give me a full refund.

TIPS & TRICKS

WEATHER: I was definitely not expecting it to be so humid, but the weather was indeed quite muggy during my visit last August. Shorts and sunscreen are a must during the day! Also, I think it’s very important to note that it wasn’t windy at all! The famous nickname actually has nothing to do with the weather and supposedly comes from a term created by 1890 journalists describing long winded, Illinois politicians who were full of hot air…just one of the many fun facts that I learned on the Wendella River Cruise 😉
TRAFFIC: I would consider the traffic to be moderate compared to places like Los Angeles and New York City. The streets are definitely busy, but cars move along at a steady pace.
THE “L”: The rail car that I rode in was clean, comfortable, and quiet which made my overall experience very pleasant.
UBER: I was surprised that Ubers take a bit long to arrive compared to other cities I’ve traveled to in recent years. Despite this, ride share services are easily available throughout the city.
SAFETY: I felt very safe the entire time I was strolling through Chicago both during the day and in the evening. I also felt safe riding the L Train. The only thing that caught me off guard was the security check point at Millennial Park when we wanted to see Cloud Gate. I’ve never had to walk through a metal detector or have my purse checked when entering a public green space, but my friend mentioned that it was a newly implemented tactic to prevent some of the recent daytime crime that was occurring in popular areas of the city. Please note that this was in August of 2022, and the security checkpoint may have only been a temporary fixture.

HERE’S A LIST OF SOME OF THE OTHER ACTIVITIES I’D LIKE TO DO THE NEXT TIME I VISIT CHICAGO

Indulge in some deep dish pizza
Catch a Cubs game at Wrigley Field
Kayak up and down the Chicago River
Enjoy a full beach day at Lake Michigan
Wander a few of Chicago’s world class museums
Visit Frank Lloyd Wright’s home & studio in the nearby suburb of Oak Park
Spend more time strolling through Millennial Park and the other outdoor landmarks & gardens located throughout the city

As you can see there are plenty of things to do during a 48-hour stay in Chicago and even more activities to experience if you have ample time to explore. Here I am enjoying the best of what Chicago has to offer 😉

Thanks to my friend P.C. for capturing the images above.

I hope you enjoyed reading this brief, Chicago visitors guide as much as I enjoyed writing it.

If you have any favorite things to do in or around the city – please let me know in the comments below.

Until then…

Safe Travels!!