Chicago is a city that's as bold as its deep-dish pizza and as vibrant as its jazz scene. It captivates with its cultural diversity, awe-inspiring architecture, and electric urban atmosphere. You know what they say — come for the Bean, stay for the blues, and leave with a heart full of Windy City charm.
If you’re lucky to have a trip to Chicago in the works, the following itinerary and tips will certainly make your life much easier, starting with a few simple answers. What is the best time to visit Chicago? Any! What to see in Chicago in one week? Plenty! Here is a list of things to do in Chicago in 1 week.
Important things to know before visiting Chicago
The burning question on everyone's mind is often the safety of Chicago, so let's address it right away. Chicago, being a major metropolis, is generally safe, but it's vital to recognize its diversity in neighborhoods. Some are welcoming, while others might warrant caution. To keep your chances of getting mugged to a minimum, stay alert to your surroundings and steer clear of dimly lit or desolate areas, especially when walking alone.
Among other things to know before you go is the weather. Chicago's nickname as the “Windy City” is no joke. If your trip falls outside summer months, be prepared to layer up and have warm jackets on standby. The best time to visit Chicago is summer, as it strikes a pleasant balance between scorching heat and bone-chilling cold. However, the other seasons have their own charms, provided you come well-prepared!
One of Chicago's greatest assets is its public transportation system. During your one week in Chicago Itinerary, there are high chances you won't require anything beyond the L. What is this elusive and mysterious “L”, you might be asking yourself? The L is a local metro system that mostly runs above the ground. It’s not just fast and efficient, but it is also an entertaining way to soak in the city's sights as you traverse its routes all day long.
Getting in and out of Chicago Airport
Chicago is one of those cities with great public transportation to and from the airport. So if you are flying into Chicago O’Hare Airport, the best and cheapest way to get to the city itself is by public transport. The CTA Blue Line train connects the airport to downtown Chicago. The whole trip takes about 45 minutes and will cost you only $5.
Pro tip: If you plan to use public transport during the whole stay, buy an unlimited pass. A day pass is only $5, and a 7-day one is $20 (the airport ride included).
A taxi ride from the airport would cost you around $40 and, depending on traffic, might be either a faster way to get to the city or a nightmare. Renting a car is always an option (especially for such an enormous city as Chicago), but only if you plan on using it throughout your trip.
Is going to Chicago for a week worth it?
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A short answer is yes! Chicago is always diverse and is ready to surprise you with its world-class museums, iconic architecture, vibrant neighborhoods, and complicated past. The trip length breakdown goes as follows: Visiting Chicago in 1 day would give you time to see only a couple of major sights, in 2 days you’ll learn how to navigate it, and in 3 days you are guaranteed to get a general feel for the city. The ultimate best-case scenario — a perfect week in Chicago — will allow you to build a relationship with this place and discover the hidden gems of the city.
Chicago is not just about the sights and places though, as it is also a true cultural hub. It shows different sides with different seasons and events. If you’re here in autumn, you will see a jazzy and artsy Chicago, if you are here in spring your favorite holiday will become St. Patrick’s Day — no other city in the US celebrates it on such a grand scale. So don’t worry about things to do in Chicago for a week, the city has got plenty.
Itinerary for one week in Chicago — what to do?
From taking a selfie in front of the famous Bean to catching a free live jazz session in a neighborhood bar, spend one week in Chicago by checking off all the must-see tourist bucket list items and more! Here is a short overview of our Chicago one-week guide:
Chicago Day 1: Fill the day with the best places to visit in Chicago in 1 day. Start your introduction to the city with a visit to iconic landmarks like Millennium Park and the Art Institute of Chicago. End your day with a performance at the legendary Chicago Theatre.
Chicago Day 2: Take in breathtaking views from the 360 CHICAGO observation deck, stroll along the scenic Riverwalk, and immerse yourself in the Roaring Twenties ambiance at the Green Mill jazz club.
Chicago Day 3: Discover the beauty of Lincoln Park, soak up the sun at North Avenue Beach, and explore the charming Old Town neighborhood.
Chicago Day 4: Embark on the Bloomingdale Trail, immerse yourself in the Garfield Park Conservatory‘s lush greenery, and experience the vibrant energy of the West Loop.
Chicago Day 5: Take a captivating tour of Chicago's gangsters and ghosts or embark on an architecture-centered river cruise, and let the rhythm of live music guide your evening at the Empty Bottle.
Chicago Day 6: Venture into the South Side, marvel at the Buckingham Fountain, explore the wonders of the Field Museum, and immerse yourself in the authentic atmosphere of Chinatown.
Chicago Day 7: Journey to Hyde Park, capture stunning views from Promontory Point, wander through the University of Chicago campus, and immerse yourself in the lively atmosphere of Woodlawn Tap.
Are you excited for all the action? Without further ado, here’s a day-by-day detailed itinerary of what you can do in Chicago for a week.
Day 1
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Start your day bright and early and first of all visit the Bean (officially known as Cloud Gate), one of Chicago's most iconic landmarks. The Bean is a giant, reflective sculpture located in Millennium Park. It's a very popular spot for taking pictures, which is why mornings are the best time to marvel at its beauty at its quietest.
Side note: Due to maintenance works, access to the Bean is limited at the moment. The construction is set to last until spring of 2024.
While you’re in this neighborhood, take your time to properly enjoy Millennium Park and its attractions.
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Among the must-see things are:
- Crown Fountain — an interactive installation with video screens that show the faces of Chicago residents. Visitors can walk through the fountain and be sprayed with water from the towers.
- Boeing Galleries — an open-air exhibition space that will surprise you. It’s one of the things even the locals keep an eye on.
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- Lurie Garden — a beautiful oasis of wildlife right in the heart of Chicago. It is a naturalistic garden designed to mimic the natural beauty of the surrounding landscape.
- BP Pedestrian Bridge — walking this 925-foot-long winding bridge will take your breath away. It provides a fantastic view of the city skyline and Millennium Park.
Spend your afternoon wandering through the halls of the Art Institute, one of Chicago’s most popular museums. It has a fantastic collection of paintings and art objects: Paying a visit to this reservoir of all things art is worth every penny of your admission fee. Our personal favorites on show here are Hopper’s Nighthawk and Chagall’s America Windows.
We suggest you finish your first day at the Chicago Theatre, a legendary venue and one of the first large, lavish movie palaces in the US. There are a lot of great shows to see in the theatre nowadays, but if nothing fits your schedule and you just want to take a sneak peek at the venue — there are public tours on Friday and Saturday afternoons for $20.
Day 2
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Chicago is such a beautiful and diverse city that just collecting views of it from different points can become an adventure of its own. To prove the sentiment, you can start your second day at the 360 CHICAGO observation deck on the 94th floor of the John Hancock Center. You'll be able to see all of the city's major landmarks, including Millennium Park, Wrigley Field, and Lake Michigan. The view is breathtaking — it is also a great spot to enjoy the magic of the city lights at night while sipping a drink at the CloudBar. Prices for the deck vary — with the cheapest starting at $30.
After taking in the views, head down to the Chicago Riverwalk for a stroll. The Riverwalk is a scenic walkway that winds its way through downtown Chicago. It’s hard to believe that what was once a neglected industrial area now has transformed into such a vibrant space. The Riverwalk ends with the Navy Pier not far from the Historic Water Tower — another beautiful urban park where you can stare at the endlessness of Lake Michigan or take a ride on a Ferris Wheel. It is also a great place to have lunch and have one of the most Chicago experiences — trying the deep-dish pizza. Giordano’s is the legendary chain that makes it best.
No visit to Chicago would be complete without immersing yourself in the intoxicating ambiance of the Roaring Twenties. Begin your evening with a journey to the Green Mill, heralded as one of the city's premier jazz clubs. While it may be a bit of a trek to reach, rest assured, the experience is well worth the effort.
Day 3
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Kickstart your third day by discovering a new neighborhood in Chicago — Lincoln Park. This sprawling urban oasis offers a refreshing escape from the city's hustle and bustle. As you wander through the park's scenic pathways, you'll encounter charming bridges, peaceful lagoons, and lush greenery. The Lincoln Park Conservatory is a must-visit; stepping inside feels like entering a tropical paradise, surrounded by vibrant, exotic plants. And don't forget the Lincoln Park Zoo — one of the few American zoos that are free!
After soaking in the natural beauty of Lincoln Park, head over to North Avenue Beach. Here you'll catch some killer views of Lake Michigan and the city’s skyscrapers. Feel the wind in your hair walking through the beach or just soak up some rays, — whatever floats your boat, you’ll find yourself an activity to fill your time with at the beach. As the sun starts to dip, find your way to Old Town, a place dripping with history and character.
Old Town is your playground for nightlife activities. There are plenty of spots to grab a bite, so pick a place that catches your eye. One of the cool spots in Chicago to grab drinks is actually here: The Old Town Ale House is a historic joint that's been serving up drinks for ages. Kick back, soak in the atmosphere, and enjoy a drink or two. Let the good times roll and savor the unique vibes of Chicago's oldest bar. Here's to a day well spent!
Day 4
Today is the day to learn about the cultural diversity of Chicago. Start your day with a dose of fresh air and urban exploration on the Bloomingdale Trail, better known as the 606. When they say Chicago is a walkable city, this is what they mean! This elevated trail allows you to stroll through different Chicago neighborhoods and discover a unique perspective of the city.
Next up, make your way to the Garfield Park Conservatory, a lush sanctuary tucked away in the West Side. Here, you'll step into a realm of flourishing flora and vibrant blossoms, where tropical and arid climates seamlessly merge. Explore the diverse rooms, each presenting a distinct ecosystem of its own. What's even better? You don’t have to pay a dime to get in, so it’s one of the best things to do for free in Chicago. Afterwards, it's time to dive into the neighborhoods. Head to the West Loop, a trendy district brimming with culinary delights and artistic flair. Allow yourself to get lost in the captivating energy of this dynamic part of the city, and if time permits, explore other nearby neighborhoods, each with its own distinct personality.
End your day at the Empty Bottle, a legendary spot in the Ukrainian Village known for its rock and indie music scene. Whether you're a music enthusiast or just looking for a lively night out, this venue promises an unforgettable experience. Catch a live show, revel in the electric atmosphere, and maybe even discover your new favorite band.
Day 5
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You've been exploring Chicago for a while now, getting a real feel for the city. But here's the thing about this place — it never runs out of surprises. There's always a new side to discover. So, why not take a breather and let someone else lead the way? Chicago's got a bunch of cool tours. One of our favorites is dedicated to gangsters and ghosts of the city. It's a blast, super informative, and more memorable than your typical sightseeing tour. Whether you're a die-hard Al Capone buff or just love a good Tom Hardy flick, you're in for a good time.
Now, if you're up for a different kind of adventure, hop on a river cruise! There's a bunch of options to choose from, catering to all tastes. See the famous architectural marvels — Champagne bottle building or Jewelers building — from a new angle. It could be a chill sunset cruise or a deep dive into the history of Chicago — you pick. Just be sure to check the schedule and weather before you set sail.
If you prefer to explore Chicago’s top sights at your own pace (or just want a basic tour of the city, without all the extra embellishments), then a hop-on hop-off bus should be your ultimate pick. An open-top double-decker bus is the epitome of old-school excursions, so curb your nostalgia by getting a ticket (there are two versions, 24- and 48-hour access available).
Day 6
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Now, let's venture down to the South Side of Chicago. You might have noticed by now that this city boasts an unexpected wealth of parks and green spaces. Here's another gem to add to your list: Grant Park. The heart of this park is none other than Buckingham Fountain, and it never fails to leave us in awe. Seriously, it's a sight you won't tire of — one of the biggest fountains in the world, adorned with giant seahorse statues, Buckingham Fountain puts up a spectacular light and music show every evening.
Keep heading south and you’ll find yourself by the Field Museum. It’s one of the world's largest and most famous natural history museums. It’s probably not something you would put on your Chicago one-day itinerary, but it’s definitely a museum to visit during your 7 days in Chicago. Tourists with kids love going to Shedd Aquarium, which is conveniently located next to the Field Museum. It’s indoor and impressive — your inner kid would also enjoy the experience.
While in this area, make sure to take a peek at Chinatown — one of the largest in the United States. Wander its streets, lined with charming shops and beautifully detailed architecture. Check out lesser-known skyline views of Chicago from Ping Tom Memorial Park. Cap off your day with a meal at one of the many family-owned joints, as these places serve food so flavorful your taste buds will cling to the memory of it for quite a long time.
Day 7
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When you are spending seven days in Chicago, you have the luxury to spread your wings and truly get to know the city. Today’s destination is slightly more remote from the center, but it should be in everyone’s 1-week Chicago Itinerary. Welcome to Hyde Park!
Let's start with the crown jewel — Promontory Point. It's a man-made peninsula that gives you killer views of the city. Honestly, a lot of locals swear by it as their go-to spot for taking in the skyline.
Then there's the University of Chicago campus. And it's not just for the scholars. The place is a sight to behold with its mix of Gothic, neoclassical, and modern buildings. It's definitely worth a leisurely stroll. Cinema fans might want to check out Doc Films Theatre — a student-led movie theater that always has a wonderful program from classic flicks to cult favorites.
Last but not least, wrap up your day at Woodlawn Tap — this place is something else. You've got students, PhD professors, and regular blue-collar folks all mingling. And every Sunday, they host a free jazz jam session. So, plan your visit accordingly.
Day trips from Chicago
If at any point of your stay in Chicago you feel like you want to diversify your trip — get outside of the city! That’s the beauty of 7 days in Chicago — it allows you to expand. We’ve prepared a couple of destinations you can add to your one-week in Chicago itinerary.
- Indiana Dunes National Park — just an hour's drive from Chicago, it’s an absolute gem for a casual day trip. Put on your most comfortable walking shoes and hike the Dunes. There are over 50 miles of hiking trails that will offer you breathtaking views and fond memories.
- The Morton Arboretum — situated approximately half an hour west of downtown Chicago, this garden creates a distinct sense of being in a different world. The place is perfect for outdoorsy folks and art lovers — their art installations change every season and are always top-notch. If you are wondering what to do in Chicago in one week in 2024, the Morton Arboretum should be on your list.
- The Cave of the Mounds — a bit further away from the city (about a 3-hour drive), it is a unique and unforgettable experience for everyone. The cave offers both guided and self-guided tours through its wonders. If you get lucky you might spot a bat or even a salamander while marveling at the cave's stunning crystal formations. Since it's underground, the temperature is always a cool 50°F, so be sure to dress accordingly.
Where to eat in Chicago?
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The itinerary for 7 days in Chicago naturally calls for a curated list of excellent spots to relax with a cup of coffee or indulge in a delightful snack. We’ve collected a bunch of places that offer great food in Chicago and make your travel experience even better:
✔️ La Josie is a classic Mexican eatery that has three bars and a roof. The food is authentic, the drinks are delicious, and the prices are reasonable. What else would one need?
✔️ Kanela Breakfast Club is an upbeat cafe offering creative Greek-influenced brunch fare with an organic focus, plus cocktails. It has multiple locations in Chicago, so there is a good chance you’ll have one in your neighborhood.
✔️ Beatrix Market is a great option for a cheap and fast meal when you're on the go to your next Chicago adventure. They have a good coffee selection and a wide variety of fresh meal options, including salads, sandwiches, and hot dishes.
✔️ Goddess and the Baker is a popular bakery that conveniently has a full menu of breakfast, lunch, and dinner items. Besides great food, they are very environmentally friendly and compost all of their food waste.
✔️ Hero Coffee Bar is a chain of coffeehouses that are perfect for jump-starting your morning. Our favorite spot is on Jackson Blvd — it’s a great hideout to take a breather from the craziness of the city.
✔️ Intelligentsia Coffee is another cool spot for decent coffee. They are known all over the States, but their headquarters are in Chicago.
✔️ Palmer House is a hotel with stunning decor and a fleur of the 20s. Their restaurant has a desert that created an obsession all over town. If you get a moment in your busy 1-week Chicago itinerary, come down here and try their famous Palmer House Brownie.
✔️ Have you ever heard of Garrett Popcorn? Even the locals say it’s the most delicious popcorn in the world. With numerous shops peppered throughout the city, prepare to be astonished by the choice of flavors. And of course, the Chicago Mix is an absolute must-try!
✔️ If you visit Chicago for the first time, make sure your culinary journey includes dishes Chicago is known for: Giordano’s for an iconic deep-dish pizza experience and Portillo’s for a taste of the local hotdogs.
Where to stay during one week in Chicago?
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1 week in Chicago will fly by really fast with all the lists of things to do. Thus, what you need from your accommodation is a good neighborhood, a reasonable price, and a comfortable bed. Here are some options for different tastes:
- 3* Freehand Chicago — a lush and a tad grandiose hostel in the heart of Chicago that has a bar and great breakfasts. A bunk bed starts at $40, private room — from $170 per night.
- 4* Hotel Felix — eco-friendly boutique hotel that features a French-inspired eatery & a lounge. Price: $130 per night.
- 4* Warwick Allerton Chicago — a wonderful hotel choice if you’re looking for something elegant and sophisticated. Its rich history dates back to the Roaring Twenties. Prices start from $140 per night.
It might be a good idea to check out Airbnb options as well, as seven days in the city might make you miss home vibes.
Important note: There is a city tax put on tourist accommodation. You will have to pay 4.5% of the price for a hotel and 10.5% for Airbnb.
More tips for visiting Chicago in 2024
Now that the most urgent questions like how many days to spend in Chicago or what to do in Chicago for one week are answered, let us give you just a couple of tips.
As with any touristic hub, Chicago has a Go City Chicago Pass. A digital pass gives you access to all the important attractions throughout the city. If you plan to visit most of them — consider buying one. There are several types of the passes — check them out while planning your one-week in Chicago itinerary.
Getting around Chicago
Once again — Chicago’s public transportation system is a real lifesaver. It will get you anywhere you want in a decent amount of time.
The most efficient way is to use buses and the rail system. Buy a Ventra card and keep it in your wallet all the time. The fares are:
- $2.25 per bus ride; $2.50 per train ride
- 24-hour pass: $5
- 7-day pass: $20
Another fun and scenic way to discover Chicago is by water taxi. It’s a cheap alternative to a water cruise. There are three routes and several ticket options worth checking out.
And finally, the best answer to the question of what to do in Chicago in one week in 2024 is to walk! Many of the major attractions are located within walking distance of each other.
The perfect one week in Chicago: in conclusion
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We really hope that we’ve managed to ease your travel anxieties by providing you with the detailed Chicago itinerary, as well as the necessary tips and tricks that might come in handy once you set foot in the Windy City. Still, if you have any further questions regarding the topic, feel free to leave them in the comments down below.