Courtesy of 360 CHICAGO
The “Windy City” offers a wealth of cultural and entertainment options that provide a refreshing contrast to the more subdued vibe of Minnesota. The storied metropolis is brimming with iconic landmarks and revered cuisine and is a popular destination for many Minnesotans—thanks in large part to its proximity and ease of access. For those living in the Twin Cities, Chicago is only about a six- to eight-hour drive away, or direct flights to Chicago’s O’Hare and Midway airports are plentiful and typically inexpensive, taking less than an hour and a half by air.
One of my favorite things about Chicago is the famed “L” train system, with its elevated tracks weaving through the downtown—the arteries that pump the lifeblood through the city. As you walk the streets below, the rumble of the train cars overhead is a constant, ever-present soundtrack to the bustling urban life. The electric hum that builds in volume, followed by the thunderous clatter as the cars rattle along the tracks, the air filling with the hissing of brakes. There’s something so old-timey about the rust-covered steel beams, a feeling of nostalgia (perhaps, because they date back to the 1890s). Nonetheless, the rail system sees upwards of 317,000-plus passengers every day.
My husband and I recently visited Chicago, and with only 48 hours to explore, we packed in some of the best experiences the city has to offer. Whether you’re traveling solo, with a partner, or with the whole family, the sky(scraper) is the limit. You could spend a day exploring the renowned Chicago History Museum, stroll through the striking architecture of the city’s downtown along the river, or take in the energy of Navy Pier. When hunger strikes, you’ll find an incredibly diverse dining scene, from deep-dish pizza to innovative farm-to-table fare. And for nightlife, Chicago’s hole-in-the-wall bars, comedy clubs, and live music venues provide endless options for evening entertainment. Here’s how we made the most out of our two days in Chicago, from where we stayed to where we played.
Korean-inspired Hospitality
Located in the heart of downtown, the L7 Chicago by Lotte hotel offers convenience, uber-chic decor (think traditional Korean art with a modern twist), and exceptional guest service rooted in Korean hospitality. Modern in-room amenities include an espresso station, a yoga mat and two dumbbells, and souvenir rubber-soled bootie socks. Each room is also equipped with a state-of-the-art air purification system, so you can breathe (and sleep) better.
You’d never know the building dates to 1912 and was once the headquarters of D.B. Fisk Co., the largest wholesale millinery in the nation. Our room had the cutest cushioned window nook with breathtaking views of the Chicago River and surrounding skyline. Plus, the central location along the Riverwalk makes it an ideal base for exploring on foot.
Courtesy of L7 Chicago by Lotte
Exploring the City
On our first day, we wasted no time taking the fastest elevator in America to the top of the city, with a visit to the 360 Chicago Observation Deck, located on the 94th floor of the John Hancock Center. The observation deck offers floor-to-ceiling panoramic views of the city and Lake Michigan from 1,000 feet above the Magnificent Mile. For the more adventurous (and stronger stomached), the TILT experience tilts you out over the city for a thrilling perspective.
Photo by Alesha Taylor
For a dose of culture (and because I’m a literature lover), we started our second morning with a visit to the American Writers Museum. This interactive museum celebrates the lives and works of American writers—such as Hemingway, Twain, Steinbeck, and Dickinson—and offers exhibits that delve into the creative process and literary history. It’s an inspiring stop for bibliophiles—and the museum features family-friendly displays and activities, making it an educational and enjoyable experience for visitors of all ages.
My husband and I love Segway tours—probably a little too much. We feel it’s a great way to get a unique perspective of the city, while also seeing a lot more sites than walking allows. On our second day, we landed on a downtown tour with Absolutely Chicago Segway Tours, where we spent two hours gliding through the bustling streets and along the lakefront, stopping at Millennium and Grant parks, Buckingham Fountain, and the Museum Campus (which, arguably so, offers one of the best hidden-gem views of the Chicago skyline). The guided tour provides insightful commentary on Chicago’s history and architecture, making it both an informative and fun way to explore. Most tours have age restrictions for Segway riders, but bike rentals are a great alternative for families with younger children.
Photo by Alesha Taylor
Nightlife and Entertainment
Chicago’s nightlife is as dynamic as the city itself, with plenty of options to keep you entertained into the night. Before dinner at Gene & Georgetti on our first evening, we stopped by Pizzeria Due—the little brother of renowned Pizzeria Uno. The atmosphere was old school, dating back to 1955, with a wood-paneled maze leading to the bar and restaurant. The walls are lined with antique memorabilia, Shakespeare quotes, and black-and-white marquee photographs. Though we weren’t there for pizza, Pizzeria Due is known for its Chicago-style deep-dish pies. We sipped on locally made cider, while watching “The Sandlot” on the bar TVs.
Photo by Timothy Schmidt
On our second night, we were lucky enough to catch a show at The Second City, Chicago’s legendary comedy club. Known for launching the careers of many famous comedians—including Chris Farley, Tina Fey, and Steve Carell—The Second City offers hilarious performances that will leave you in stitches. Whether you’re a fan of improv or sketch comedy, the talent and wit on display are impressive. Note that some shows might have age restrictions, so check the schedule for family-friendly performances.
After the show, we grabbed a drink at Snickers, a cozy corner bar that reminded us of an elevated American Legion vibe (ambient lighting, yet inviting). The Rolling Stones were in town during our visit, so locals and visitors alike were donned in all things Hot Lips, while belting out their best impersonations of Mick Jagger. We could tell the bar takes pride in offering an extensive range of drinks, from classic cocktails and craft beers to fine wines and nonalcoholic options, ensuring there’s something for everyone. And the cocktails are cheap, too.
Family-friendly Activities
Though we weren’t traveling with any littles, Chicago caters to families with an array of engaging activities. While we were having lunch at The Dearborn right after our flight landed, we couldn’t help but notice every couple minutes, a family would stop dead in their tracks right outside the window where we were seated. It turns out, on the other side of the glass, there was a clue to a family-friendly scavenger hunt called Urban Adventure Quest. It essentially turns the city into a giant game board, while players solve clues and complete challenges, all while learning local history.
A famous lakeside Chicago attraction, Shedd Aquarium, is home to thousands of aquatic animals from around the world. Kids will love the interactive exhibits, touch tanks, and the opportunity to see dolphins, beluga whales, and sea otters up close. The aquatic show is a must-see, showcasing the incredible abilities of the aquarium’s marine residents. Shedd Aquarium is also one of the only places in the country where you can book a 45-minute penguin encounter. Another great family-friendly option is the Field Museum, where you can explore exhibits on natural history, ancient civilizations, and dinosaurs. The museum’s crown jewel is Sue, the largest and most complete T. rex skeleton ever discovered. Interactive displays and hands-on activities ensure that young visitors remain engaged and entertained.
Photo by Alesha Taylor
Navy Pier is a popular waterfront destination in Chicago that offers a variety of fun activities for families. Some top attractions include the Ferris wheel, which provides panoramic views of Lake Michigan and the Chicago skyline, the Chicago Children’s Museum with interactive exhibits, and Pier Park which has a mini-golf course, butterfly house, and more.
WHERE TO EAT IN CHICAGO
Try these Chicago specialties during your next visit
THE DEARBORN
145 N. Dearborn St.; thedearborntavern.com
Tall ceilings, tile-lined walls, and ample window seating abound at The Dearborn—and the food is equally as big on flavor. We tried the famous flaky, yet crispy Fish and Chips—Chef Aaron Cuschieri actually beat Bobby Flay with his recipe. Don’t forget to order the Parker House Rolls, served with duck fat butter. For dessert, the beignets rival New Orleans’ Cafe du Mond.
ROBERT’S PIZZA & DOUGH CO.
465 N. McClurg Court; robertspizzacompany.com
For pizza lovers, a visit here is a must. Renowned for its perfect crust and creative toppings, Robert’s Pizza is a delightful experience for all ages. We tried the Meatballs, a combo of veal and beef, plus red sauce and giardiniera. Next up was the Carne pizza, topped with crumbled fennel sausage, meatballs, cup and char pepperoni, and fresh mozzarella. The waterfront location adds to the charm, offering picturesque views as you savor your meal (just don’t feed the ducks).
BAR SOL
700 E. Grand Ave.; barsolnavypier.com
If you’re seeking seafood, head to Bar Sol. This eclectic eatery on Navy Pier serves a fusion of Latin and American cuisines, with an array of small plates and craft cocktails. The chips and homemade hot salsa appetizer was delicious, with just the right amount of heat. We also tried the Fajita Platter, which included steak (you can also choose chicken or shrimp), chimichurri potatoes, black beans, guac, and salsa. The vibrant décor and lively ambiance make Bar Sol a great spot for lunch with a view or for a night out.
GENE & GEORGETTI
500 N. Franklin St.; geneandgeorgetti.com
No trip to Chicago is complete without excellent Italian food, and Gene & Georgetti does not disappoint. Established in 1941, it’s the longest-operating Italian steakhouse in Chicago. We tried the delicious Gnocchi alla Norma, which features homemade gnocchi, sauteed eggplant, basil, and creamy mozzarella di bufala. The Prime NY Strip was char-broiled to perfection—and shareable. Lastly, the Chicken Joe was a steaming heap of juicy roasted chicken with sweet and hot peppers. It’s named after a Gene & Georgetti waiter from the ’70s and has been on the menu ever since.
