Will I eat enough deep dish pizza? How magnificent is the mile? Is it always cold? We’ve prioritized the best of the best to ensure you have an authentic experience and we’ve answered your most pressing questions. Whether it’s your first time, or you are coming back for more, our guide to 48 hours in the Windy City will leave you full, exhausted, and slightly buzzed.
The Basics
Arrival
Whether you are flying into O’Hare or Midway, public transportation via the “L” trains take you to the heart of the city and are easy to find in both airports. Depending on traffic and time of day, this very well could be the quickest route, otherwise both Uber and taxis are readily available.
Lodging
To maximize your 48 hour stay in the Windy City, we recommend staying in River North, the Gold Coast, or Streeterville. Want to deep dive into our picks for hotels? Check out our Chicago Hotels Guide.
Transportation
A mix of L trains, bikes, scooters, and ride shares will be your best bet. Renting a car is not recommended.
Get Your Culture On
Aside from your list of must-see cultural/tourist attractions, here are some slightly off the beaten path to consider.
CHICAGO ARCHITECTURE TOUR
When the weather isn’t treacherous and the boats are still in service, there’s no better way to see Chicago than from the river. Traversing downtown through a canyon of towering skyscrapers is highly recommended. Several companies offer tours—but Wendella has been doing it since 1935—if you’re interested in the architecture, you may as well get the expert’s perspective on a Chicago Architecture Foundation tour. Otherwise, the Chicago Water Taxi is recommended for a carefree trip.
KEEP IN MIND
Make sure to check the weather and dress appropriately. It can get very breezy on the water—you’re in the Windy City, after all.
LIVE MUSIC AT THE GREEN MILL
"Classic Chicago" doesn't begin to describe the Green Mill. Step into the past at this vintage jazz club, where you can watch world-class music acts from the same booth Al Capone once called his own (hint: it's the one you can see both entrances from).
KEEP IN MIND
Don't expect the drinks to be as fancy as the decor. Go for the vibe, not the cocktail menu. And hit the ATM, it’s CASH ONLY.
IMPROV AT SECOND CITY
If an actor on TV has made you laugh any time in the last 50 years, odds are good that that person got their start at The Second City. The oldest and most venerated of Chicago’s many comedy theaters, The Second City brings their world-famous sketch comedy revues to gut-busting life seven days a week.
KEEP IN MIND
Comedy doesn’t have MPAA ratings, so expect any children in attendance to learn some fun new words.
WRIGLEY FIELD
Even if you don’t care about baseball, a visit to Wrigley Field is a Chicago necessity. It’s arguably the most famous stadium in all of baseball—hell, all of sports—having been around since 1914. Grab a bag of peanuts, a Chicago dog, too many beers, and take in the ivy-covered outfield walls and the historic scoreboard and enjoy the game. If you want a...different...experience, grab some cheap bleacher seats. Just don’t wear nice shoes.
KEEP IN MIND
Getting tickets isn’t always easy, so buy early or pay a hefty toll. Speaking of hefty tolls, you’re better off taking an Uber or the Red Line than trying to park.
Neighborhoods to Stroll
STREETERVILLE & LAKESHORE DRIVE
There’s only one street in Streeterville you need concern yourself with: Michigan Avenue. Dubbed The Magnificent Mile, the stores on Michigan Ave will help you go from being asked, “What are you wearing?” to “Who are you wearing?” with just a simple swipe of a credit card. If shopping isn’t high on your list during your visit, start your walk closer to the Chicago River and Millenium Park.
TOURIST-Y GUILTY PLEASURE
The Chicago Architecture River Cruise is hands down the best way to take in the city’s fascinating architectural history from front row seats on the Chicago River. You also can’t miss a photo op in front of the famous ‘Bean’ (aka Cloudgate) in Millenium Park.
WICKER PARK & BUCKTOWN
It’s hard to say where Wicker Park starts and Bucktown ends, but if skyrocketing property values are any indication, the entire neighborhood is a hot commodity. Despite recent hipster migrations to Logan Square, Humboldt Park, and Pilsen; Wicker Park and Bucktown are still Chicago’s go-to areas for a bespectacled spectacle of beards, bikes, and baristas.
TOURIST-Y GUILTY PLEASURE
The 606 is Chicago’s answer to New York City High Line—the 2.7-mile trail set out along an old railway line allows for bikers, runners, and pedestrians to scoff at the peasants below.
Photo courtesy of The 606
LINCOLN PARK
Lincoln Park is one of city’s ritziest neighborhoods, as evidenced by the many upscale boutiques, restaurants, and homes that line its streets. The neighborhood sits just north of downtown along the sprawling lakefront public park that shares its name. The park itself is home to running and biking trails, the Lincoln Park Zoo, and the largest farmers’ market in the city.
TOURIST-Y GUILTY PLEASURE
The Lincoln Park Zoo. Why? It’s free and there are animals. No brainer.
Deep dive into Our Favorite Chicago Neighborhoods and Chicago's Best Neighborhoods for Dining Out.
