The Perfect 3-Day Chicago Itinerary

Planning a 3-day trip to Chicago? This itinerary is infused with local knowledge and insider recommendations for a perfect 3-day trip to Chicago.

Chicago might be the 8th most visited city in the U.S., but it’s quickly becoming #1 in my heart. The Midwestern warmth oozes from this urban hub, brimming with world-renowned architecture and boasting some of the best food you’ll find anywhere in the country. After countless trips to Chicago, I’ve curated the perfect 3-day itinerary for food and architecture lovers visiting the city. Complete with details about where to stay, where to eat, and how to get around, this itinerary will act as your ultimate travel guide to Chicago.

Home to deep-dish pizza, five professional sports teams, and one of the largest art museums in the world— welcome to Chicago! Whether you’re hunting down a laugh at a comedy club, searching for good beer, or eager to learn about the city’s Black History, this Midwes gem has something for everyone. And I’ve included it all in this extensive itinerary.

about Chicago ↴

Chicago is prime for tourism thanks to an easy-to-navigate public transportation system (that’s also incredibly affordable) and a Midwestern warmth that makes every encounter with locals a pleasant one. The city sprawls from the edge of Lake Michigan (one of the primary causes for its constant wind) into 77 community areas that house an estimate 3 million residents, many of whom you’d probably recognize, including former President Barack Obama, Oprah Winfrey, Billy Zane, and the late Robin Williams.

When people talk about the food and arts scene in Chicago being world-class, they aren’t speaking in hyperboles. The city is home to over 200 theaters, 250 live music venues 60 museums, and more than 7,000 restaurants. It’s also a progressive city known for hiring the first full-time film critic and building the world’s first skyscraper, and being the first to televise a presidential election debate.

No matter what name you know Chicago by (“the Windy City”, “Chi-beria”, “the Second City”, etc.), its impression on everyone who visits is inarguable. Much like its sister city, New York, Chicago has a unique story, including one of the most well-known fires in the United States, the start of the famous Route 66 drive, and a river that runs backward.

is Chicago safe ↴

It feels important to note safety whenever I write about American cities. Whenever I encounter foreign travelers planning a trip to the US, safety concerns (rightfully) become a topic of conversation. I hope it’s reassuring to know that I have never experienced an uncomfortable or unsafe situation in Chicago. Violence in Chicago is thankfully experiencing a downward trend, and most instances of violence are concentrated in small geographic areas of the city you’d be unlikely to stumble into as a tourist. What most travelers should be aware of is petty theft. Having a bag with a zipper and keeping a good handle on your phone, like you would in any busy city, is your best defense against thieves. Bad things can happen anywhere, so please travel with your wits about you.

where is Chicago ↴

Located on the shore of Lake Michigan, Chicago is a true Midwest city. Contrary to what many believe, Chicago is not the capital of Illinois. However, it is the state’s biggest city and its cultural and economic epicenter.

1.5-hour drive from Milwaukee, Wisconsin
4-hour drive from Bloomington, Indiana
40-minute drive from Indiana Dunes National Park
4-hour flight from New York City, New York

the best time to visit Chicago ↴

Being a Midwest city, it’s no surprise that Chicago’s temperatures fluctuate dramatically. It’s also important to note that Chicago earns its nickname as the “Windy City” tenfold.

Spring | Spring is a great time to visit the city if you don’t mind gambling with the weather. From April through the beginning of June, Chicago’s flowers start to bloom filling Millenium Park with beds of color. The temperatures average between 40° F and 70° F, meaning you might need a puffer jacket, or you could very well be walking around in a t-shirt.
Summer | Chicago’s hottest months are between June and August when temperatures regularly hit 90° F. Despite summer in Chicago being the hottest and most expensive time of the year to visit, it’s also the most exciting time to be there (and that’s coming from a huge proponent of shoulder season travel). Music Festivals, baseball games, and vibey rooftop bars make summer in Chicago truly unbeatable.
Autumn | In September, the temperatures in Chicago hover around 70° F. However, as autumn settles in, the October and November temperatures drop significantly. The trade off? Fewer crowds to contend with and, if you can time your visit right, lovely orange and red shades sprinkling the city’s trees.
Winter | You can chalk the lack of crowds and cheap flights to Chicago from November through March down to one thing: the bitter cold. Listen, I’m from Montana, so I know “cold”. But Chicago cold is something different entirely. Think negative temperatures and a cold lake breeze that creates a frigid wind chill.

how to get to Chicago ↴

Chicago has two airports: Midway + O’Hare. O’Hare is where most of the city’s international flights arrive and depart, and is home to a majority of the major airlines. Midway, by contrast, is the budget airline airport where you’ll find most domestic flights. From either airport, it’s easy to get to the city via “the L” or an Uber. The L is more economical, but both will get you there. If you’re planning on using public transport during your time in Chicago, I recommend purchasing a Midway and O’Hare are equidistant from the city center, so there isn’t much of a difference as far as travel time is concerned, just keep in mind the traffic.

Many people visiting Chicago are domestic travelers from within the US. And, as the US is a vehicle-heavy culture, many road trip here. The carless can opt for arriving by Amtrak!

how to get around Chicago ↴

Once you you make it to the city, the best way to explore is on foot. Walking around, one of the best ways to explore the city is on foot. Chicago’s downtown is very walkable and one of the best ways to see all the sights!

The public transport in Chicago puts the rest of the Midwest to shame, so I recommend you take full advantage. The L, short for “elevated train”, can get you almost anywhere for next to nothing. To ride, simply purchase a ticket at any station.

Alternatively, there are plenty of taxis throughout the city, but downloading the Uber or Lyft apps will help ensure you get a ride on a cold night. I’ve found Uber and Lyft more cost-effective than traditional taxis, but they aren’t nearly as affordable as riding the L (and they’re not as much of an experience).

where to stay in Chicago ↴

best area of Chicago to stay in

West Loop | West Loop has a banging nightlife scene and feels a touch closer to “local” Chicago than downtown, where most buildings are commercial.
Fulton Market | Fulton Market is my top recommendation when people ask where to stay in Chicago. The area is swimming in restaurants and cafés for the food-obsessed traveler, as well as close to many of the city’s best museums and architectural wonders.
“The Loop” | You’ll hear people refer to “The Loop” when speaking about downtown Chicago. Essentially, it encompasses the main attractions and the city center. Hotels will be more expensive here and it’s quite touristy, but you’ll be right in the heart of Chicago (and you are a tourist afterall).

Best hotels in Chicago

Found Hotels Chicago | Ideally located within a 12-minute walk of Navy Pier, Millennium Park, and all the other top attractions and landmarks, Found Chicago was the right spot for a first-time explorer of the Windy City. Some of the amenities for guests of Found Chicago include validated parking, luggage storage for those who arrive before check-in or need a safe space for their items after check-out, yummy-smelling and refillable toiletries in all the bathrooms, 24/7 reception desk, fresh linens and towels, and USB plugs for travelers who may have forgotten their adaptors. On top of the hotel's stunning design, I’d say the biggest perk was the included parking, which can cost an arm and a leg in the city.
Silversmith Hotel | Located in the city’s “Jewelry District”, the Silversmith Hotel is an upscale hotel within walking distance from Millenium Park, Pizano’s Pizza, and the Art Institute of Chicago. The rooms at the Silversmith are huge, and the staff showcase Midwestern hospitality at its finest. There is valet parking here and, although a bit expensive, having your vehicle parked safely while you explore the city is worth it. The hotel is just steps from the L train, so you can wander using public transport instead of dealing with the hassle of Chicago parking.
The Hoxton | With a stunning bar, spacious co-working space, and atmospheric rooftop, you could hardly ask for anything more than what the Hoxton Chicago provides its guests. The design details of this West Loop locale are impeccable.

Other highly rated accommodation in Chicago:

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3-day Chicago itinerary ↴

Day 1: west loop, Union Station, WNDR, Art Institute of Chicago, Pizano’s Pizza + Pasta, Millenium Park, Cloud Gate, Grant Park, Navy Pier (optional), The Second City (comedy show)

The West Loop is a great place to start when introducing yourself to Chicago. Begin the day with breakfast or brunch at one of the area’s many eateries. Brite Donuts is a wholesale bakery that serves Metric Coffee, bread, and pastries all day. It’s the perfect place to stop in if you’d prefer a grab-and-go breakfast. Try their braided brioche dough with horchata glaze.

West Loop is also home to the ultra luxurious Aire Ancient Baths. Candles light this intimate bath house in the basement of one of West Loop’s historic industrial buildings. This is an idyllic spot for relaxation. Book in a massage or a salt scrub before hitting the concrete city streets of Chicago.

You might not be in the mood for a hot water soak, in which case I suggest stopping by Union Station. If you’ve ever watched the Julia Roberts’ classic My Best Friend’s Wedding, you’ve seen the inside of this architectural gem. This Chicago landmark opened in 1925 as a replacement for the city’s original train station. Today, it’s a hub for the Amtrak.

Another worth West Loop stop is WNDR, an interactive “museum” that highlights works by Yayoi Kusama. Some of its most notable exhibits in “The Mirror Room” where you’ll find yourself surrounded by mirror balls and mirror-lined walls. Those who have visited the TeamLab in Tokyo and enjoyed it will love WNDR. It is USD $39 per adult to get in, but if you’re interested in immersive artwork, it’s worth every penny.

The Art Institute of Chicago is a must-visit whether you’re a museum-goer or not. The collection of art here is exceptional, as you might expect from one of the largest art museums in the world. Renowned for its Impressionist exhibits, the Art Institute houses some of the world’s most recognizable works of art. I recommend spending at least 2 hours exploring the expansive museum. I cannot stress enough how impressive it is, even if you aren’t an avid art consumer. Tickets, which can be purchased online or in person, are a bit of a spend at USD $32 per adult. Luckily, children under 14 get in free, as well as Illinois educators, WIC cardholders, and Chicago teens under 18. Illinois residents also get free access on certain days. Check their website to find out more about their discounted entry. It’s open Thursday through Monday.

After all the art, you’re going to want to sit down and grab lunch. Walk to nearby Pizano’s Pizza and Pasta for a truly “Chicago” experience. When I mentioned the friendly atmosphere of the city, I wasn’t kidding. On top of Pizano’s having some of the best deep dish pizza and pasta in the country, it also has a reputation for service thanks to one particular server: Joe “The Chach” Chacho. There are literally entire articles dedicated to him on the internet. I didn’t know about the star of Pizano’s until my mother and I were sat at one of his tables. He’s worked at the eatery for 40+ years and is known for giving out free desserts. An individual deep dish here feeds two easily (I promise), as does a single serve of their famous homemade pasta (try the gnocchi). I recommend coming with friends and sharing the meal, or else you’ll risk wasting food.

Walk off lunch with a stroll through Millenium Park, home to the iconic Cloud Gate art installation. Commonly known as “The Bean”, Cloud Gate was designed by an Indian-British artist in 2006. To bring his vision to life, he seamlessly welded 168 stainless steel plates together in the shape of a cloud (or a bean). The installation has become emblematic of the city, and is the centerpiece of Millenium Park. It’s impossible to miss due to the crowds that form around it, eagerly taking photos. Unfortunately, as of April 2024, Cloud Gate is under construction. Hopefully, views of The Bean will be unobstructed once more.

Walking south from Millenium Park will take you to Grant Park, home to the Lollapalooza Music Festival. It’s not especially noteworthy outside of Buckingham Fountain, but if you happen to be in Chicago during the summer, the green space is definitely worth a visit. Another optional itinerary stop is Navy Pier. Now, here’s the honest truth from someone who has spent a lot of time in Chicago: Navy Pier isn’t that impressive. There is a ferris wheel and botanical gardens that you might be interested in, but overall I would skip it if I were short on time.

Did you even go to Chicago if you didn’t see a show at The Second City? This comedy club is responsible for producing some of the all-time greats, including Bill Murray, Catherine O’Hara, Jim Belushi, Tina Fey, and Steve Carell (just to name a few). Close out your first day in Chicago with laughs at the famous comedy show. You can purchase tickets online.

Day 2: Secret Food Tour, Chicago Mahogany Tours, Wrigley Field, + theater show

This wouldn’t be a foodie itinerary without mention of a food tour. Chicago’s food scene lends itself beautifully to belly-led tours, and there are a number of fantastic ones I recommend for hungry travelers.

Food tours to consider in Chicago:

Yes Chef Chicago Food Tour | For fans of “The Bear”, this 3.5-hour food tour includes show filming locations and a LOT of food.
Secret Food Tours Chicago | A locally-led 3-hour tour with six food stops located around The Loop.

For those who would rather find food on their own, I recommend spending your day on a Chicago Mahogany Tour of the city. This is a Black-owned business aimed at preserving the city’s rich cultural history. This tour has come so highly recommended by so many locals, but I’ve never had the time to take one myself. I’m always in Chicago spontaneously, without time to book the tour in advance. With the slogan “Everything dope about America comes from Chicago”, this is at the top of my Chicago bucket list. Dilla, the Chicago urban historian who leads the tours, has gone viral on TikTok for his 60-second history lessons.

Any baseball fans out there? If you’re heading to Chicago, you need to visit Wrigley Field. It is a must for any baseball (or sports) fan. There’s nothing more American than a hot dog at the ball field, am I right?! Wrigley Field is the second oldest stadium in Major League Baseball, making it a historical landmark and one of the best places in the country to watch a ballgame. Wrigley is surrounded by an electric village of pubs and restaurants. If your visit doesn’t time with baseball season (or a home game), you can still tour the stadium, its field, and the dugout.

Chicago’s flourishing art scene extends to the performing arts. With over 250 live music venues, a professional ballet company, and more than 200 theaters, it feels criminal not to add a theater show of some variety to your itinerary.

Day 3: Chicago Donuts, architecture river cruise + Willis Tower or Hancock Tower

Start your third day in Chicago with donuts! The city has no shortage of donut shops, but I recommend grabbing some from Do-Rite Donuts + Chicken. Their buttermilk old-fashioneds are to die for! Do-rite also have a selection of gluten-free and vegan donut options, so it’s an inclusive addition to your food itinerary. Doughnut Vault is also a fantastic way to kickstart any Chicago day, but get there early! They have a line around the block almost daily and once everything is sold out the shop closes. I love the old-fashioneds here, but I also recommend their honey bun. If you don’t mind traveling a bit, Smack Dab Chicago have a mouthwatering vegan breakfast sandwich, giant cinnamon rolls, and some of the best vegan donuts I’ve ever tasted anywhere the world over. No matter where you land, you’re sure to leave filled and fueled for a final day of Windy City adventure.

Taking an architectural tour of Chicago by river boat is a must-do, and it’s the perfect way to close out your time in Chicago. I suggest booking a Chicago Architecture Center River Cruise (CAC tour) to learn about the city’s rich architectural history. One note: it’s better in warmer weather. I took a cruise with Wendella Tours on a November day and while I learned more than I could have imagined about the buildings that line Chicago’s river, I was also freezing, which admittedly took away from the experience a bit. The next time I took the tour with CAC on a warm summer day and the entire experience was 10/10, no notes.

Now that you’ve learned about the architecture surrounding you, head to Willis Tower for views of the city from above. Willis Tower, known as the Sears Tower until 2009, was once the tallest building in the world. While it no longer holds that title, the tower still looms above the Chicago skyline standing at over 1,700 feet. You can purchase a ticket to the Skydeck viewing platform and step out onto the 103rd floor glass deck. The Skydeck is included in the Chicago CityPASS, which helps you save money on the city’s main attractions.

Alternatively, views from the top of the Hancock Tower are comparable and the tower is, typically, not nearly as crowded and is much less expensive to visit. Many locals actually prefer Hancock over Willis Tower— something to keep in mind if you’re choosing between the two. If you have time and are interested, I suggest heading to both. Otherwise, Hancock tower has just as good of a view and you won’t have to deal with the Willis Tower wait time.

You’ve officially completed three days in Chicago. It’s time now to head home or onward to your next destination. I highly recommend traveling onward to Milwaukee or nipping down to Indianapolis.

where to eat in Chicago ↴

You might (wrongly) assume that Chicago being a Midwest city means it’s a sea of tasteless steak and potatoes. But, if you learn anything about Chicago from this itinerary, let it be this: it’s the foodies. In 2023, Chicago was ranked the 4th best food city in the US after New York, New Orleans, and Los Angeles. The city is home to 21 Michelin-star kitchens, including restaurants showcasing Filipino, Mexican, and Indian cuisine. All of that to say, you should come to Chicago ready and eager to eat!

must-try food in Chicago

Hot dogs | In the 1840s, German immigrants began making their way to the Midwest United States, bringing with them the culinary tradition of sausages. During the Great Depression, however, it became necessary for “sausages” to be made from the cheaper cuts of meat (ie trimmings). In the decades since, the Chicago-style hot dog emerged as an all-beef frankfurter on a poppy seed bun smothered in green relish and yellow mustard.
Gourmet popcorn | Chicago-style popcorn is one of the city’s lesser-known delights. Invented by Garret’s Popcorn in 1988, the gourmet popcorn mixes cheese popcorn with its caramel counterpart. You’ll find this for sell across the city and at its many sports stadiums.
Deep dish pizza | It’s no secret that Chicago serves up the best deep dish pizza in the game. Chicago-style pizza, commonly called “deep dish”, has a thick, pie-like crust. It’s deeper and less bready than Detroit-style pizza. Deep-dish pizzas are topping-heavy, piled with cheese, and served in large round pans.
Authentic Indian + Pakistani food | Devon Avenue is renowned for its authentic Indian eateries thanks to its high concentration of South Asian immigrants, particularly those of Indian and Pakistani descent. The curries along the avenue are a true taste of India and Pakistan, respectfully.

best deep-dish pizza in Chicago

Uno | The story goes that in 1943, Uno’s founder, Ike Sewell, invented the Chicago-style deep-dish pizza.
Pizano’s Pizza + Pasta | Pizano’s earns my recommendation for the best deep dish in Chicago. Portions here are massive, even by American standards, so split with a travel partner if you can. One individual deep-dish pizza can easily feed two people (I promise).
Pequod’s | Fans of “The Bear” will know locals get their deep dish from Pequod’s.
Giordano’s | Giordano’s is fine if you’re looking to taste deep dish and don’t care much about an “authentic” Chicago experience, but it’s become a chain over the years and thus has sort of lost its soul. Still, the deep dish here is good. I just find it a bit expensive for the atmosphere you get.
Lou Malnati’s | I like that Lou Malnati’s sells individual deep dish, so you aren’t overwhelmed by the task of eating an entire pie by yourself. The owners of Malnati’s is the same as that of Pizano’s, but I prefer (and recommend) Pizano’s for overall experience.
Labriola | Deep dish pizza and homemade Italian pastas fill the menu at Labriola, but Stan’s Donuts (located inside the restaurant) is my favorite reason to visit.

famous food spots in Chicago

Portillo’s | Portillo’s is quite the experience. A line out the door caused hilarity in the form of total chaos inside the corner restaurant. One side of the building, which was stuffed with antique oddities, served up pasta and sandwiches while the other side bagged Chicago-style hot dogs and sodas. Order numbers were being yelled out and there were zero tables free inside, but we thought it was worth visiting once, though many locals claim the food quality has gone downhill over the decades.
Kasama | You may notice this spot from its cameo in “The Bear”. Despite opening during the COVID pandemic in 2020, owners Tim Flores and Genie Kwon saw Kasama flourish thanks to its innovative pastries and Filipino-infused brunch menu. Creative takes on lumpia and tocino are just a few of the many dishes that have quickly made Kasama a Chicago establishment. It’s even won the highly sought-after James Beard Award
Ever | If fine dining tasting menus in ultra-luxe eating environments are your thing, consider making a reservation at Ever. Michelin-star rated and highly praised for its exquisite service, Ever is for foodies who are willing to spend on world-class culinary experiences.
The Girl + The Goat | The Girl and The Goat is one of Chicago’s most well-known restaurants. Just the thought of the chickpea fritters and wood-fired broccoli makes me salivate. However, it’s the restaurant’s goat dishes (you read that right) that it’s famed for. As a vegetarian, I’ve never tried the goat here, but several friends rave about the goat empanadas and confit goat belly. If you want to eat here, a reservation is necessary.

best coffee in Chicago

Intelligenista | Great coffee, though they are actually known for their signature Matcha Limeade, which I can attest to being the perfect summertime drink.
Lula Cafe | Chef Jason Hammel opened Lula Café in 1999 with a mission to keep community at the center of the meal-time experience. The café is a no-frills all-day café famed for its stuffed breakfast burrito and
Caffe Umbria
Sawada Coffee

best desserts in Chicago

Levain | Sure, it’s a New York chain, but the chocolate chip cookies from Levain live up to their viral hype. It’s well-worth stopping by their Chicago location if you’re int he market for a sweet treat.
Goddess + The Baker| Known for its abundance of saccharine baked goods, including cakes, cookies, and pastries.