Wondering what to do in Chicago for a weekend? Well, prepare to be blown away (bad pun intended) by this jam-packed itinerary for the Windy City!
Located on the shores of scenic Lake Michigan, Chicago is the 3rd biggest city in the United States. It’s also one of my absolute favorites to visit. I’ve been to Chi-town so many times at this point that I’ve lost count.
With all that research under my belt, here’s all you need to help you plan an awesome Chicago 2-day itinerary. Get ready to hit the sights like Navy Pier, and then reward yourself with a deep-dish pizza feast.
Let’s get to it and see what you can get up to with a weekend in Chicago.
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2-Day Chicago Itinerary (With a Bonus Day!)
This itinerary is two full days with a bonus day at the end. Assuming you get in on a Friday, you can follow this Chicago 2-day itinerary for Saturday and Sunday and do the bonus day on Friday or Monday, depending on your travel schedule.
By the way, you should plan a trip to Chicago when the weather is nice. The best time to visit Chicago is definitely between May and October. Winters are harsh here, and they can start early and/or last a bit too long. The best Chicago activities are outside and aren’t very enjoyable in the winter months.
On this itinerary, you’ll stick mostly to the downtown area, known as “the Loop.” With just a few days in the Windy City, most of the fun stuff to do in Chicago is in this area. The bonus day includes a trip outside of the Loop, though, so you can check out a local side of the city as well.
- Museum Campus
- Grant Park & Millennium Park
- River cruise
- Navy Pier
- Deep dish pizza
- Art Institute of Chicago
- Architecture walk
- Chicago Dogs
- Willis Tower Skydeck
- Dinner and a show
- Lincoln Park
- Beach day
One of the best free things to do in Chicago is simply admiring the city’s gorgeous skyline towering above Lake Michigan. For these epic views, start your day in the Windy City at Museum Campus.
By the way, a pro tip for this Chicago 2-day itinerary is to bring comfortable walking shoes or rent a bike. You’re going to cover a lot of ground in a short amount of time!
Once you get down to Museum Campus, start by heading to the Adler Planetarium. From here, you can look across Lake Michigan to get that amazing panoramic view of the city’s iconic skyline. If you’re feeling up for it, drop in and check out the planetarium ($19, open every day from 9-4).
You’ll also find the fantastic Shedd Aquarium ($39.95, open every day from 9-6) and the Field Museum ($26, open every day from 9-5) in this area. All three are excellent choices, but you’ll have to pick just one for time’s sake. Of the three, the Field Museum is the most interesting. I mean, they have an entire T-rex fossil here! Get your all-access pass to the Field Museum here.
Grant Park and Millenium Park
Heading north from Museum Campus, you’ll arrive in Grant Park. There are several beautiful gardens, sculptures, and fountains here. It’s the perfect spot to grab a coffee and a snack, plop down on a bench, and enjoy some solid people-watching.
Next up is Millenium Park, where you can gain an appreciation for the funky art and architecture of Chicago. Be sure to check out the Jay Pritzker Pavilion as well as the Cloud Gate, otherwise known as “The Bean.”
It’s not all about the lake here. We can’t forget about the Chicago River running right through downtown.
While it’s enjoyable on foot or bike, one of the top 10 things to do in Chicago is definitely taking a river cruise. The Chicago Architecture Foundation Center runs a popular cruise on the First Lady. Tickets cost $48, and the cruise lasts around 90 minutes. Or, check this river architecture tour out.
If you want to linger along the river, there are plenty of places to grab a drink with a view. Head to the Northman Beer & Cider Garden for your craft beer fix, City Winery for some vino, or hit up Island Party Hut for a tiki vibe.
Deep Dish Pizza
When people ask what to do in Chicago, one thing that always comes up is the city’s famous pizza. They do deep-dish style here, which basically means eating a brick of cheese. Good thing you’ve earned it after logging all those miles!
There seems to be a deep-dish pizza place on every corner in downtown Chicago. They’re not all created equal, though. Some of the most highly-rated spots include Lou Malnati’s and Giordano’s. Both have locations near the river, so you don’t need to travel too far.
If you have any energy left after that massive day, there’s no shortage of things to do in Chicago at night. For a nightcap, why not head to one of the city’s rooftop bars for more views?
Art Institute of Chicago
After grabbing some breakfast, it’s time to tackle day two of this beast of an itinerary. A must-do in Chicago is definitely the Art Institute ($25, open Monday and Thursday-Sunday from 11-6). It’s also conveniently the jumping-off point for the walking tour to follow.
The impressive collection here spans centuries and genres. Their exhibitions are always changing, and there’s enough to see on any given day to keep you busy for several hours. Tickets cost $25.
Chicago Hot Dogs
You’ve had the pizza already, the top dish Chicago is known for. Now it’s time to try a classic Chicago-style hot dog. There’s a lot going on here for what’s usually such a simple dish, resulting in an explosion of flavor.
A Chicago-style dog is an all-beef sausage in a poppy seed bun. It’s topped with diced onion, sweet pickle relish, sport peppers, tomatoes, a pickle spear, and yellow mustard.
The Relish Chicago Hot Dogs stand is just a few blocks south of the museum, and it’s great for a quick lunch fix. It’s also worth the detour to head to Portillo’s, as they have lots more on the menu if you want a full lunch.
There’s no question that the Chicago-style hot dog is among the best in the country. What do you think? Leave a comment at the end with your favorite dog!
Did you know that the first skyscraper was built in Chicago? Well, it was way back in 1885. It rose from the ashes of the Great Fire of 1871, which left much of the city in ruins. Architects looked to the sky, and things have never been the same again!
There are plenty of options for architecture tours if you want a guide. A great option for a self-guided tour is the Loop Art Tour on Wikitravel. It’s one of the best free things to do in Chicago.
The tour has 21 stops, but you won’t need to hit them all. You can skip the Millenium Park portion, having done it on day one. Once you reach the end, we’ve come to our next stop.
Willis Tower Skydeck
Remember staring out at the Chicago skyline to start day one? That building you saw towering above all the rest is the Willis Tower, formerly the Sears Tower.
Built in 1974, this 108-story building was the tallest in the world for 25 years. While it’s now #23 (which just so happens to be Michael Jordan’s number, by the way), it’s still an impressive sight.
After the ear-popping elevator ride to the Skydeck ($30, open every day 9 a.m.-10 p.m.), you’ll be able to enjoy some insane views of the Windy City. If you’re feeling brave enough, step out onto “The Ledge” and look straight down. It’s a bit vertigo-inducing, but it sure is cool!
If you time it right, you can be at the Skydeck before sunset. That way, you get to enjoy both a day and night perspective and watch the city light up.
Dinner and a Show
Hopefully, you’ve still got some energy left because you can’t miss out on some live music in the Windy City! Chicago has an out-of-this-world music scene with shows of every genre and size on a nightly basis.
Before dancing the night away, though, you’ll want to get yourself a nice dinner. Trying different restaurants is one of the top Chicago activities.
You can literally find any type of cuisine here to suit any budget. Check out some recommendations below in the “Where to Eat in Chicago” section.
As far as evening entertainment goes, you’re spoiled for choices. In addition to live music, you can choose between theatrical performances, stand-up comedy, and much more. Check out this list of venues to get started.
Day 3 (Bonus Day!)
If you find yourself with another half day in Chicago on the front or back end of your trip, look no further than Lincoln Park. Not only is it a beautiful place to explore, but it’s also one of the top free things to do in Chicago!
There’s plenty to see and do in Lincoln Park. Here you’ll find a zoo, conservatory, driving range/mini-golf, and even a beach. It’s the place to be on a nice summer day!
If chilling on the beach isn’t your thing, you can always rent a bike, kayak, or stand-up paddleboard (SUP) for a bit more action. Once you’ve had your fill playing outside, the nearby neighborhoods of Park West and Lincoln Park provide tons of options for food and drink.
How to Get to Chicago
If you’re flying into the Windy City, you have two different options. O’Hare (ORD) is the bigger of the two airports with lots of options for direct flights. It’s about 15 miles northwest of downtown, which takes about an hour on the Blue Line.
The other airport is Midway (MDW), which is on the south side of Chicago. It’s is primarily a hub for Southwest Airlines. You can get to and from Midway via the Orange Line.
Chicago is also accessible via both train and bus. Amtrak has several routes that travel to Union Station downtown. A super cool travel experience is taking the California Zephyr train that goes all the way from Chicago through Denver and on to San Francisco. It’s one of the most scenic train rides in America and definitely a bucket-list trip!
How to Get Around Chicago
American cities are not exactly known for their excellent public transportation options. Thankfully, Chicago bucks this trend. The city has an efficient public transport system that will get you everywhere you want to go.
Upon arrival, you’ll want to get a Ventra card from a vending machine. For $20, you can get a 3-day pass to ride the subway. It’s known locally as the “L” because it’s on “EL-evated tracks.” You can also hop on the bus but probably won’t need to for this Chicago 2-day itinerary.
Taxis are also plentiful here and they’re more affordable than in places like New York City or Los Angeles. Both Uber and Lyft also operate in Chicago and are really convenient to use.
If you’re thinking about driving in Chicago, don’t. Parking can be very difficult to find or incredibly expensive. Plus, you can’t imbibe in adult beverages if you’ve got to drive, and that’s no fun.
For all the ground you cover in this itinerary, it’s not a bad idea to rent a bike. The Divvy bike-share program is pretty huge and it’s easy to find bikes downtown. It costs $15 a day for unlimited rides of up to 3 hours each.
When to Visit Chicago
Once again, the best time to visit Chicago is definitely from late spring to early fall. Winter can be downright miserable here with below-freezing temperatures and chilly winds blowing in from Lake Michigan.
To take advantage of all the best things about Chicago, warmer weather is a must. Coming in April-May or September-October helps to avoid the summer crowds a bit and you’ll still get nice weather.
That being said, the city is definitely at its most exciting during the summer months. This is when you’ll find a bunch of music and food festivals going on, which are tons of fun. There’s the Taste of Chicago, Lollapalooza, Chicago Craft Beer Festival, and plenty of others.
Where to Stay in Chicago
Chicago is a huge city with a nearly endless array of accommodation. From budget youth hostels up to 5-star hotels, quaint boutiques to local options via Airbnb and VRBO, there’s something for every style and budget here.
To help you figure out where to stay in Chicago, here are some recommendations. They are all in the downtown area as that’s where the bulk of this itinerary takes place:
- Budget—HI Chicago: This Hostelling International location is smack dab in the middle of downtown Chicago, giving you easy access to all the city’s best sights at a budget rate. It’s also a great place to meet fellow travelers.
- Mid-Range —Central Loop Hotel: Located just a few blocks from the Art Institute and Millenium Park, this boutique hotel is a great spot to rest your head after a busy day of exploring Chicago without breaking the bank.
- Luxury – The Langham: This 5-star hotel is right on the river and is quite luxurious. It’s got multiple dining options, a pool, spa, and a massive club on the top floor with some epic panoramic views.
Where to Eat in Chicago
Consider yourself a foodie? Well, then my friend you’re going to love a weekend in Chicago! You already know about the famous hot dogs and deep-dish pizza in the itinerary, but here are some more recommendations for other meals:
- Breakfast: Yolk, Meli Cafe, Wildberry Pancakes and Cafe
- Chicago Hot Dogs: Portillo’s, Al’s Italian Beef, Relish
- Deep Dish Pizza: Lou Malnati’s, Giordano’s, Pequod’s
- Vegetarian/Vegan: sweetgreen, Native Foods, Freshii
- Fine Dining: Oriole, The Gage, Bavette’s Bar & Boeuf
Chicago is Waiting for You!
Well, I hope you enjoy this whirlwind tour of Chicago. One thing’s for sure—you’ll be planning your return trip before this one is even finished. It’s the kind of city you can go back to again, year after year. There are so many things to do that it can be tough to plan a weekend in Chicago. Having said that, this itinerary will be tough to beat. I know I’m excited about my next visit, even if it’s going to be the 75th one!
This is a post written by contributor, Sasha. He is a teacher, writer, and video producer from Detroit, Michigan. He graduated from Michigan State (Go Green!) and has since lived in China, Indonesia, Mexico, and Colombia. Sasha and his wife Rachel run Grateful Gypsies, where they write about teaching ESL, digital nomad life, long-term travel, live music, and more.
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