Weekend Trips from NYC: A 24-Hour Chicago Itinerary
If you’ve ever wondered whether a weekend getaway from New York could feel like a full vacation, this guide proves it’s possible. Chicago is less than a two-hour flight from NYC and makes for the perfect quick weekend trip or even a 24-hour adventure if you’re short on time (or trying to save on hotels).
I flew to Chicago to photograph Chicagohenge, the phenomenon when the sun aligns with the city grid, something I’ve tracked in Manhattan for years. Unfortunately (but typical), the weather wasn’t cooperating, so what started as a photography mission turned into a foodie weekend. Below, you’ll find a practical 24-hour itinerary in Chicago of what to see, eat, and do in a single day in the Windy City.
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Why Chicago Makes the Perfect Weekend Trip from NYC
Chicago’s frequent short flights from the tri-state area, compact downtown, and easy public transportation make it a top pick for weekend trips from NYC. You can land the same morning and be in the heart of the city by lunchtime. For my corporate peers who still work 9-to-5s, that accessibility makes it ideal for travelers who want a change of scenery without burning through their PTO.
Can You Really Explore Chicago in Just 24 Hours?
Yes, the key to a successful Chicago 24-hour itinerary is to focus on a few core experiences. Keep your schedule light and stay central. If you’re like me, who no longer plans for trips and just shows up, Chi-town makes it super easy to navigate. Disclaimer: You won’t see everything, but you’ll feel the pulse of the city right away. In just one weekend, you can cover food, architecture, and the local landscape.
How to Get From NYC to Chicago for a Weekend
Flights from NYC to Chicago take around two hours, with regular service from JFK, LaGuardia, and Newark on the major airlines like American, United, and JetBlue. etc. Morning departures let you start exploring before noon, while late-evening returns make a 24-hour Chicago itinerary totally doable.
Once you land at O’Hare International Airport, skip the Uber and take the Blue Line ‘L’, Chicago’s 24-hour rapid transit train that runs directly between O’Hare and downtown. I’m a major proponent of public transportation, and it’s the most affordable and efficient option—just $5 from O’Hare. Compared to NYC’s AirTrain, that’s a significantly better deal. A regular ride elsewhere on the ‘L’ is $2.50, and if you’re planning to hop around the city, just opt for a 1-Day CTA Pass since it’s also $5, and gives you unlimited rides for 24 hours.
Where to Stay for a Weekend Trip to Chicago
If you’re stretching your NYC day trip into a weekend getaway, stay close to downtown for maximum convenience. For my first time visiting, I checked into InterContinental Chicago Magnificent Mile, a 1920s architectural landmark steeped in Roaring Twenties grandeur and a member of Historic Hotels of America.
When I travel, I usually collaborate with hotels in exchange for content creation to keep my costs down, but this time I booked using IHG points with my IHG Premier credit card, securing the room with 99,000 points. My King Classic City View Grand Tower room offered a great vantage point.
While I appreciated the old architecture of the hotel, the wear and tear was pretty obvious. Since the InterContinental brand is part of IHG’s Luxury & Lifestyle collection, I was expecting a higher standard, but this is why the points game is worth it. However, maybe not for the room I stayed in, which seemed to be an ADA-accessible room. Usually, I wouldn’t care, but there was no edge of the tub, which made showering a bit tricky since all the water would leak all over the floor. Additionally, there wasn’t much shelf space in the bathroom, which I found odd.
Still, I didn’t have to spend a fraction as I would have had I paid for this in cash. Technically, my stay was free (except for amenity fees), which is the best kind of luxury. For a quick weekend stay, it delivered what I needed: location and comfort.
What to See First on a 24-Hour Chicago Itinerary?
A must-do activity in Chicago is visiting one of its most recognizable landmarks: Cloud Gate, better known as “The Bean.” I have no idea what the hype is about it, especially since New York City installed its own Bean Sculpture down on Leonard Street in 2023, commissioned by the same guy.
That said, it’s worth the visit. It literally takes 5 minutes. If you’re a photography enthusiast, get there early to beat the crowds and catch the skyline reflections while the city wakes up. Go right after sunrise on a weekend when the mirrored surface will be at its cleanest, and you’ll have the best light for shooting before the plaza fills up.
Where to Eat on a Short Trip to Chicago
Do-Rite Donuts
First up, head to Do-Rite Donuts, a small-batch, chef-owned shop known for bold flavors. If you’re a coffee purist, skip the pre-mixed lattes and get a classic drip; it balances better with the sweetness of the donuts.
Au Cheval
Known for serving what many may consider the best burger in America, Au Cheval is pretty solid. I usually avoid eating somewhere I could just go to in New York, but Chicago is the OG location for this. With a minimum of two patties and a runny egg on top, the burger was massive. Paired with a $10 root beer float, it had that authentic Chicago diner experience. Be sure to walk it off, strolling along the riverfront afterward!
Chicago Pizza & Oven Grinder
A local institution serving its pizza as pot pies (?!) in a cozy, brick Victorian building. Chicago Pizza & Oven Grinder was the top recommendation from my boyfriend, who’s been to Chicago before and was in charge of the food tour. He was so excited to come back here. The pot pie is so DENSE, weighing in as a half-pound or a pound entree.
Be sure to also order the Mediterranean Bread as an appetizer. I always say carbs are friends, but even I had to admit, this was way too many carbs for a weekend!
The Purple Pig
Michelin Guide–recognized and James Beard–awarded, The Purple Pig serves Mediterranean-inspired small plates in a lively space. I was seated at the bar right away, even without a reservation. The food was decent, nothing stood out, and prices were New York–comparable. I guess it’s warranted considering all the accolades.
Things to do in Chicago on a Weekend Trip from NYC
Walk the Riverfront
To be honest, besides eating, all I really did was walk around. There was no checklist. If you’ve read my other travel guides, you’ll know that the older I get, I’ve simply stopped planning my trips altogether and just go with the flow. Walking is the best way to get to know a new place (and rack up your steps while you’re at it
Start in The Loop, the heart of downtown Chicago. The elevated train lines, historic architecture, and glass towers instantly give you a sense of place. From there, wander over to the Chicago Riverwalk, where you can sit by the water and watch boats drift by.
Explore Navy Pier or the Lakefront
Hop on a bus and head toward Navy Pier or the Adler Planetarium for some of the best panoramic skyline views in the city. Chicago’s free lakefront trail stretches for miles, offering plenty of spots to sit, stroll, or just watch the waves roll in. The peaceful juxtaposition against a city’s busy urban core is one of my favorite contrasts to experience.
The Power of Quick Adventures
You don’t need weeks off or a long-haul flight to feel like you’ve traveled. Sometimes, a short weekend trip from NYC, even just 24 hours, can reset your perspective completely. Whether it’s Chicago this time or Boston, Philadelphia, or D.C. next, these quick getaways are a reminder that travel doesn’t need a passport. Just a packed bag and a willingness to go.
I didn’t get my Chicagohenge shot this time, but I did get the experience of visiting a new city in a short amount of time. Weekend trips allow a quick getaway with a simple change of scenery, some good meals, and the walk between them.
FAQ – People Also Ask
Q: What cities are best for weekend trips from NYC?
A: Philadelphia, Chicago, Boston, and Washington, D.C. are popular options with short flights or train routes from New York.
Q: Is a day trip to Chicago worth it?
A: Absolutely. With good planning, you can experience the city’s highlights, such as The Bean, Riverwalk, and classic food spots in a single day, and be home before bedtime.
Q: What’s the best way to get from NYC to Chicago for a short trip?
A: Nonstop flights from JFK, LaGuardia, or Newark to ORD or MDW take under two hours.
Q: How do I plan a 24-hour itinerary in a new city?
A: Focus on four key elements: one iconic landmark, one meal, one neighborhood walk, and one scenic sunset.
Watch My Weekend Trip in Chicago on YouTube
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