The Perfect 48 Hours in Chicago
As someone who's always on the lookout for the perfect weekend getaway, I can't help but rave about Chicago. It's hands down one of my favorite destinations for a quick big city fix, and for good reason.
Unlike the overwhelming hustle of New York, Chicago offers all the excitement of a major metropolis but with a more manageable, Midwest charm that makes it perfect for a 48-hour adventure.
Every time I visit the Windy City, I'm struck by how easy it is to dive right into the action. The city's layout is intuitive, the public transit is a breeze, and you can pack so much into just a couple of days without feeling like you're running a marathon.
From world-class museums and stunning architecture to a food scene that'll make your taste buds dance, Chicago has it all.
One of the things I love most about my Chicago weekends is the variety. No matter what I'm in the mood for, I know I'll find it here.
Craving some culture? I'll catch a show at one of the city's renowned theaters or comedy clubs.
Feeling hungry? Deep-dish pizza, gourmet hot dogs, or Michelin-starred restaurants – take your pick.
And don't even get me started on the nightlife. From cozy blues bars to rooftop lounges with skyline views, there's always somewhere exciting to end the night.
It's a city that invites exploration, whether you're wandering through the vibrant streets of Wicker Park or taking in the breathtaking views along the lakefront.
So, if you're looking for a weekend escape that packs all the excitement of a big city into a friendly, accessible package, Chicago is your answer.
In this guide, I'm going to share with you how to make the most of 48 hours in this incredible city. Get ready for a whirlwind tour of iconic sights, hidden gems, and unforgettable experiences that'll leave you planning your next Chicago getaway before you've even left. Let's dive in!
First, where to stay
Chicago offers a wide range of accommodation options to suit various budgets and preferences. Here are some top picks for young travelers looking to make the most of their 48-hour adventure:
Common Area at Freehand Chicago
Located in River North, this trendy hostel/hotel hybrid is perfect for budget-conscious travelers who don't want to sacrifice style or location.
It offers both shared and private rooms with a hip, modern design. The on-site Broken Shaker bar is a hotspot for craft cocktails and meeting fellow travelers.
Seasonally open pool at The Hoxton, Chicago
Situated in the vibrant Fulton Market District, The Hoxton is a stylish and Instagram-worthy hotel that won't break the bank. It features a rooftop pool, multiple restaurants, and a cozy lobby perfect for working or socializing.
The rooms are compact but well-designed, with city views and comfortable beds.
Experiential focused decor at Hotel Lincoln
This quirky boutique hotel in Lincoln Park offers a more neighborhood feel while still being close to downtown.
The real draw is the J. Parker rooftop bar, which provides stunning views of the city and Lake Michigan. It's also right across from Lincoln Park Zoo and close to several beaches.
Fieldhouse Jones: For something truly unique, try this sports-themed hotel/hostel in River North.
It offers both private and shared rooms, plus fun amenities like a game room with ping pong and foosball. The eclectic decor and communal spaces make it easy to meet other travelers.
Located in the West Loop, the Ace Hotel is known for its cool, minimalist design and lively common areas. The rooftop bar, Waydown, is a great spot for evening drinks with skyline views. It's surrounded by some of the city's best restaurants and nightlife spots.
Housed in a historic Art Deco building in Wicker Park, The Robey offers a more local experience away from the downtown hustle.
The rooftop lounge, Up Room, provides panoramic views of the city. It's perfect if you want to explore Chicago's hipster haven and still have easy access to downtown via the Blue Line.
For a more homey feel or if you're traveling with a group, consider renting an apartment through Airbnb. You can find great options in neighborhoods like Wicker Park, Logan Square, or Lincoln Park, giving you a more local experience.
Tips for Choosing Accommodation:
Consider location carefully. Staying in or near River North, the Loop, or West Loop will put you close to many attractions and nightlife spots.
Look for places with good public transit access. Being near an 'L' station can save you time and money on transportation.
If you're planning on going out a lot, consider a hotel with a good bar scene or rooftop lounge.
Don't forget to factor in any resort fees or parking costs when comparing prices.
Read recent reviews to get a sense of the current state of the property and the surrounding area.
Remember, in a city like Chicago, you'll likely spend most of your time out exploring. The most important factors are a comfortable bed, a convenient location, and amenities that align with your travel style.
Whether you choose a social hostel or a chic boutique hotel, any of these options will provide a great base for your whirlwind 48 hours in the Windy City!
The Itinerary
Day 1:
Morning
Start your Chicago adventure with a hearty breakfast at Lou Mitchell's, a classic diner that's been serving up delicious meals since 1923. Their fluffy omelets and crispy hash browns are the perfect fuel for a day of exploration.
After breakfast, head to Millennium Park to snap a pic with the famous "Bean" sculpture (officially called Cloud Gate). Take a stroll through the park, enjoying the creative architecture and public art installations.
Afternoon
For lunch, grab a classic Chicago-style hot dog at Portillo's. Remember, no ketchup allowed! (or go ahead, just enjoy)
Next, take an architecture river cruise along the Chicago River. This 90-minute tour offers stunning views of the city's skyline and provides fascinating insights into Chicago's architectural history.
Evening
For dinner, experience the vibrant atmosphere of Girl & the Goat in the West Loop. Chef Stephanie Izard's innovative small plates are perfect for sharing and sampling a variety of flavors.
Night
Kick off your night at Howl at the Moon, the energetic dueling piano bar. Sing along to your favorite tunes, request songs, and enjoy the lively atmosphere. The talented performers and crowd interaction make for an unforgettable evening.
After Howl at the Moon, head to Three Dots and a Dash, a hidden tiki bar that serves up creative tropical cocktails in a fun, immersive setting. It's the perfect spot to continue your night in style.
Day 2:
Morning
Start your day with breakfast at Wildberry Pancakes and Cafe. Their signature berry bliss pancakes are a must-try.
Then, make your way to the Art Institute of Chicago. Even if you're not usually a museum person, the diverse collection here is truly impressive. Don't miss the famous "American Gothic" painting and the extensive Impressionist collection.
Afternoon
For a quick lunch, grab a slice (or two) of deep-dish pizza at Lou Malnati's. It's a Chicago institution and for good reason.
Spend the afternoon exploring the unique neighborhoods of Chicago. Take the 'L' train to Wicker Park for some vintage shopping and cool street art. Then head to Lincoln Park to visit the free Lincoln Park Zoo and enjoy the beautiful park grounds.
Evening
For dinner, try Au Cheval, famous for their incredible burgers. Be prepared for a wait, but it's worth it. If burgers aren't your thing, Pequod's Pizza offers a unique "caramelized crust" deep dish that's out of this world.
Night
Start your final night at The Whistler in Logan Square. This cocktail bar also doubles as a music venue, often featuring live jazz or indie bands.
End your Chicago adventure at Cindy's Rooftop. Located atop the Chicago Athletic Association Hotel, it offers breathtaking views of Millennium Park and Lake Michigan. Enjoy a nightcap while taking in the glittering city lights.
Additional Tips:
Get a 2-day CTA pass for unlimited rides on buses and trains.
If the weather's nice, rent a Divvy bike to explore the Lakefront Trail.
For a unique experience, try an improv show at The Second City, where many famous comedians got their start.
If you're a sports fan, try to catch a Cubs game at Wrigley Field (in season).
This itinerary gives you a taste of Chicago's iconic sights, delicious food scene, and vibrant nightlife. It's packed with activities but also allows for some flexibility to explore based on your interests.
Remember, Chicago is a big city with diverse neighborhoods, each offering its own unique vibe. Don't be afraid to wander and discover your own hidden gems along the way!
xx Kaitlyn