2 days in Chicago
Last updated on February 10th, 2026.
The 'windy city', or 'Chi-Town' as the locals call it, is one of my favorite cities in the US.
And, with just 2 days in Chicago to spend, we wanted to pack in as much as possible.
After an 8-hour flight from London, we arrived in Chicago’s O’Hare Airport and with no polar vortex in sight.
Like most places in April, Chicago blooms under the spring sunshine. Full of promise in the air, it's an ideal season for walking around and taking in the sights.
After surviving the long and tiring trek through US customs and immigration, we were happy to see the other side of the terminal building. We met some members of my extended family, and wasted no time in heading to our first destination.
What to do in 2 days in Chicago
Day 1
Go shopping
It might sound strange that the first thing we did in Chicago was to go shopping, but there's we'd a good reason.
The Fashion Outlets of Chicago is around 10 minutes from the airport. A mecca for designer brands and household names we couldn't wait to check out the bargains.
Happy shoppers
Despite my general feelings about shopping malls, I was pleasantly surprised once we were inside. The upper level caters to high-end designer stores like Gucci and Prada, while the lower level satisfies a more humble wallet.
Three hours and a few bargains later, we left Rosemont, and made our way downtown.
Visit Millennium Park
It's unthinkable to spend a weekend in Chicago without visiting Millennium Park. Top of the Chicago bucket list pyramid, it's famous for hosting outdoor concerts, and for being the home of the Cloud Gate sculpture.
More commonly known as 'The Bean' you can't miss it given its size, shape and the number of tourists hovering around it.
Stroll down the Magnificent Mile
While downtown, explore the streets and sights surrounding Michigan Avenue. The locals refer to it is as the Magnificent Mile, and it's a name you'll hear a lot when in Chicago.
The Magnificent Mile's a main attraction for tourists for shopping as well as for visiting the city's many skyscrapers. Grab a Chicago CityPASS® to see sights such as the observation deck at 360 Chicago and Skydeck and The Ledge at Willis Tower.
A short walk away is the boarding spot for the Chicago river architecture cruise. It's a relaxing way to see more of the city's impressive structures, and learn about the history behind them.
Map: downtown Chicago
Relax on North Avenue Beach
If shopping's not your thing, there's another, sandier, way to spend your 2 days in Chicago. North Avenue Beach is at the end of Michigan Avenue and is a regular go-to spot for locals.
Because it’s a city beach, it's very easy to get there by bus or taxi. Though the temperature wasn't quite being bikini weather when we were there, it's still a great place to relax and reflect.
Stroll through Lincoln Park
After a family brunch at Four Seasons Chicago we worked off the calories with a walk around Lincoln Park. On a sunny day, the Lincoln Park neighborhood and park is one of the best places to enjoy being outdoors.
Book to stay at the Four Seasons Chicago
The Lincoln Park Zoo in the park is open all year round. Entry is free and it's a good place for a budget-friendly family day out.
Cocktails at The Whistler
Last stop on day 1 was to a local bar called The Whistler (2421 N. Milwaukee Avenue). It's a bar, gallery, record label and live music venue, but the main attraction is their extensive cocktail list.
I chose a TV Funhouse, a tantalizing taste-bud concoction of rum, bourbon, cereal milk, honey and cinnamon.
A chilled end to the night
'Chicagoans' are always been unbelievably chilled, and the crowd at The Whistler only exemplifies this. A lively atmosphere, friendly crowd and Tamales for sale inside, The Whistler is a memorable way to end your night.
Day 2
Spend some time exploring a different, and less touristy, side of Chicago by visiting Wicker Park.
We fell in love with Wicker Park the first time we visited a few years prior. The independent boutique shops, and many bars and restaurants reinforce the area as a much-loved part of town.
Visit Wicker Park
The neighborhood combines individual style with a sense of community. Wicker Park is known for being a little bit on the ‘hipster’ side, given its number of vintage and independent stores.
Personally, I think Wicker Park is so appealing, and it's worth seeing on your 2 days in Chicago. What's more, you get to see another side to the city and see places where the locals frequent.
What to do in Wicker Park
Goorin Bros Chicago (1533 N Milwaukee Avenue) is a quaint hat shop about a 3-minute walk from Damen station.
Established in 1895, the ultra friendly staff is on hand to help and talk you through the beautiful selection of hats on offer. A charming shop front harking back to a past era, you’re purchasing an experience as much as a bespoke fedora.
A growling stomach brought me to the next spot in Wicker Park, Al’s Beef. Beef is big business in Chicago, and the thinly-sliced roasted beef drenched in its own juices in a sandwich bun is a mouth-watering treat.
Next up, was a step back in time with a visit to the Emporium Arcade Bar. A venue that you can easily walk past without realizing what's behind its doors, it's a novel hangout for a bit of nostalgic fun.
On one side is a long bar offering beers and spirits. On the other lies endless amusement in the form of arcade and pinball machines (i.e. Pacman and Tetris).
Swing by Logan Square
As night time fell, we moved to a nearby neighborhood called Logan Square. This quarter, just 2 metro stops from Damen to California, has a lot going on.
German roots in Logan Square
For dinner, we tried a German restaurant and beer hall called The Radler. Reinforcing Chicago’s rich German heritage, the Radler’s surroundings were anything but.
Mounted bicycles on the wall at the back, and contemporary Graffiti style prints give a modern edge to traditional Bavarian dining.
Rather than going for the traditional wurst, I chose the beer-battered perch with white beans and mussels. I followed this with a robust bourbon-based Shank’s Pony cocktail. The Radler is 'sehr gut', and I can guarantee you won't be leaving hungry or thirsty.
Nb: The Radler is now permanently closed.
See Chicago from above
The last stop during our 2 days in Chicago was a night out at Apogee.
This rooftop bar with an Asian-inspired menu is a great way to end your time in the city. First-class American service, and delicious food and drinks, it was the perfect, and slightly tipsy, way to end our trip.
Nb: Apogee is temporarily closed as at the time of this update.
Get around using the Chicago metro
With 2 days in Chicago, you don't want to spend your time stuck in traffic. The fastest and cheapest way to head downtown — particularly during the rush hour — is the Chicago 'L'.
Trains arrive every 2 to 3 minutes, and you can take some pleasure in watching the traffic from the train. We took the blue line to Damen, the train station at the heart of Wicker Park.
Where to stay in Chicago
I've two sound choices if you're looking for boutique accommodation in Chicago. The first is the fabulous Thompson Chicago.
This 4-star hotel is in the Gold Coast neighborhood, which is right near the Magnificent Mile. Its design is chic yet also homey, and if you're lucky to get a lake-view room, you won't be disappointed.
My second choice is The Robey in Wicker Park. It may not be downtown, but this Art Deco hotel is a great place to stay when in Chicago.
Two days in Chicago is not long enough
Admittedly, 2 days in Chicago wasn't enough to see, or do, everything we wanted. We missed out on visiting places like Navy Pier and riding the Centennial Wheel and exploring the Field Museum of Natural History.
Book: tickets to ride the Chicago Centennial Wheel
However, if you plan to visit for a weekend, it's more than possible to see the main sights, and a little more. You just need to plan carefully, and start your day early.
Another thing to mention are the people in Chicago. Everyone we came across was so helpful, and ready to help us whenever we asked.
What's more, the weather's superb come spring/summer, not to mention the delicious belt-busting food and drink. Once you've been, you’ll understand why it's known as one of America's best-loved cities.
Disclosure: This post may contain affiliate links, which means I may receive a commission if you click a link and purchase something that I’ve recommended. Thank you for your support.
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wow Amazing Places shared by you and Chicago is my top listed State on the United States of Americain travel list so I think your post is very helpful for me to plan my schedule thanks for your lovely blog post keep updating
Thank you
Lisa I’m a Chicagoan, and I gotta say you hit some really good spots in your post! I love Al’s Beef...and I have yet to find a decent Italian beef sandwich anywhere else in the US besides Chicago! Great post with excellent photos.
Aw it's nice to meet you! I'm from London but visit frequently as I have family there. It's a fun city and Al's Beef is wonderful!
Great stuff, I'm not actually all that far away from Chicago, so I really need to get there. This is a nice rundown of what I could hope to do in a weekend once I'm there, so thanks for the roundup!
You're welcome! I actually flew from Chicago to Toronto to check it out; it's a great city 🙂
I never visited Chicago. A friend of mine went there and she loves it. I see why 😉
It's a great city to see!
Chicago looks like an amazing place to visit and this itinerary probably fits nicely as a layover. I'd love to check out Wicker Park, and the entire city looks really easy to get around by the "L". By the way, the Cloud Gate ("Bean") certainly looks really unique and interesting!
I'm lucky to visit every year, and honestly the Bean is a great attraction in the city!
Chicago is one of my favorite cities in the world! I hope you come back again because 48 hours is definitely way too short for a city like Chicago!
I visit from London every year as I have family there 🙂
This is the post I've been waiting for! Tickets from Salt Lake City to Chicago are ridiculously cheap and I've been dying to have a weekend getaway in Chicago...once the weather warms up a bit. I am dying to get a picture of The Bean and take a ride on the L. I'm not a big shopper by any stretch of the imagination, but perusing some of the independent antique shops might be fun!
I'm sure you'll love it! I have family in Chicago, so tend to visit regularly. Enjoy the Bean, it's really a must see 🙂
I have never visited the USA, but have heard and read so many interesting things. And Chicago definitely sounds a wonderful place to explore. Thanks for taking me on a virtual journey 🙂
More than happy too! I'm lucky I've been a few times, and it's always fun!
This is a really useful itinerary covering almost all major spots of Chicago in merely 48hours. Loved the picture of Cloud Gate, I'm just assuming it's an evening click and it looks awesome 🙂 Loved your post, I'm bookmarking it right away!!
Aww thank you, that's so nice to read! Chicago is a great city, and plenty of things to see, do and photograph 🙂
I love short trips and you guys covered alot n 48 hours. I will be travelling to Newyork in January via Chicago and am saving this post ,so that I can go check out few places from this list.
I'm so thrilled to hear that! There's a lot to do, so seeing the best bits is a lot of work, but fun at the same time 🙂
Sounds like a lot of fun. As someone who goes on several 2-3 days trips and hardly any long trips, this is one awesome itinerary for me! I'm yet to explore the American continent... The cityscape from the beach is just spectacular! I wouldn't miss the bean! There have been so many movies shot here! I esp wouldn't forget it for the wedding scene in The Vow!!!
I've never heard of this film, but will certainly take a look now! Thanks for commenting, and hope you make it there soon 🙂
It sounds like you had a great trip. Was shopping one of your main reasons for the trip? The outlet sounds brilliant! Can't believe they have a traffic controller at the mall, haha. The Mile looks so pretty, I would definitely like to stop there if I go to Chicago.
They really did have a traffic controller! The mile is a lot of fun but prepare to spend if you do visit!
This is a great post! Putting all the things you can do in Chicago in just 2 days. Going to "The Bean" is on top of my list. haha!
Thank you, I really appreciate your comments. Hope you get there one day!
I didn’t know Chicago has so much to offer. I am a beach person, so North Avenue Beach appeals to me. Good to know that the beach is popular amongst locals as well. I like to explore places which are also frequented by the locals. That’s immersive travel for me. It amused me when I read that the entry to the zoo is free. I have never been to a free zoo.
Wow really?! I've actually been to many free zoos, I guess I've been lucky! Tbh you're not missing much, and Chicago has far better things to offer than the zoo 😀
Chicago is one of those US cities that I've always been intrigued by and want to travel to, along with Asheville, Savanna and New Orleans! I heard that the food in Chicago is amazing too, of course I am talking beyond the famous deep-dish pizza. Your photos are beautiful and it sounds like how I would spend my 48 hours too!
Aww that's great to hear, thank you! You should visit if you're based in North America, it's a fun city with lots to see, do and eat!
I visited the Fashion Outlet near the airport in Chicago too, I loved the Nike Store in there! My mouth started watering when you mentioned Al's Beef, I'd love to try one of those buns! I missed The Bean when I went to Chicago, you took a beautiful photo of it with not so many people there and reflecting the city.
Thanks James! Al's Beef was very good and juicy too from what I can remember! It's very hard to get an uncrowded pic of the Bean, but I did it!
I'd love to visit Chicago and check out the scenes from some of the best television shows! Also I've heard the pizza is world class, so maybe could sample that too 😉 I love the combination of the city and the beach, and Lincoln Park with some greenery just tops it off! The three course brunch at the four seasons sounds amazing, you really did your 48 hours in style!
There's only one way to travel for me, and that's in style! There's so many things to see and do, I highly recommend going 😀
I have never been to the states, but Chicago is on my list when I go! I want to see the musical Chicago in Chicago. hehe. Great 48 hour guide here too! thanx for sharing
Lol that's definitely a good bucket list item, go do it!
In 48 hours you have seen a lot in Chicago. Beach is the first thing I would go for. Shopping at outlet mall near the airport must be fun and also I bet prices would be much lesser than city ones. Cloud Gate surrounded by scenic skyline is picturesque.
You're right on all 3 points! The outlets are far cheaper and you can get some good bargains too 😀
You guys definitely covered a lot of ground in Chicago! I haven't visited the Windy City since I was a kid (The American Girl Place was the focus of that trip, lol), but I would love to go back and see it as an adult! It certainly seems like a city with plenty to do!
As I have family there, it makes it so easy, and sometimes necessary, to visit. That said, I always like to see what's new!
So much to do in Chicago and it's amazing one can achieve this much in 48 hours. I can imagine how fulfilled each of your day was. The Bean is a sight to behold. And you've got a nice pose too.?
Lol thanks Lydia! Though I think the Bean is far more impressive than me!
I love the lighting and reflection of your Bean shot. Well done. Is it just me or can you imagine the traffic cops as storm troopers with diminutive light sabers? Chicago is definitely a chill city for it's size. They just don't have the same pretense or pressure of New York or LA.
Haha I didn't see it that way to be honest, but thank you! I totally agree about Chicago; I much prefer it to LA and NYC.
That sounds like a pretty good itinerary for a 48 hour layover. From reading, I would tend to think that Wicker Park would be a favorite for me too, not to mention the beach and the shopping. The food also has a well known reputation, so I guess there's quite a few reasons to visit the windy city!
Chicago's a fun city, and I always love to return to see what's new!