Long Weekend in Chicago: Essential Itinerary to Spend 3 Days in Chicago For First Timers
Spending a long weekend (3 days) in Chicago? This 3 day Chicago itinerary shows you the best places to go and eat in Chicago. This itinerary also gives you many Chicago planning tips if this is your first time in Chicago.
Planning a trip to the Windy City for 3 days or a long weekend? You are in the right place!
From iconic architecture and world-class museums to deep-dish pizza and blues music, Chicago has something for everyone. Whether you’re a history buff, foodie, art lover, or just looking to soak up the urban energy, Chicago won’t disappoint.
I had been to Chicago previously in the winter and it was pretty miserable to be honest. But going there in the summer and early fall is a completely different (and amazing) experience.
In this 3 day long weekend Chicago itinerary I will show you the best places to see in Chicago and how to most efficiently spend 3 days in Chicago. I will also address practical information like how to get around Chicago, how to save money on attractions, where to eat and stay in Chicago for your perfect Chicago trip.
This blog contains occasional affiliate links, where I receive a small commission on sales of the products/hotels that are linked at no additional cost to you. In addition, as an Amazon Associate, I earn from qualifying purchases.
When’s the Best Time to Visit Chicago For A Long Weekend?
NOT in the winter! Ok I think we all know winter is brutal in Chicago so that’s the worst time to visit Chicago. I went to Chicago once in February and it was just pure misery.
Early Summer and early fall are the best time to visit Chicago with the warmer temperature and beautiful weather. In particular, the month of June, September, and October are great to visit Chicago because it does get quite hot and humid in July and August.
The shoulder seasons are generally cheaper and less crowded than the peak summer season and you can enjoy a lot of outdoor activities. Although if you do have to visit Chicago in the summer at least you can enjoy the beach near the city center.
Where to Stay in Chicago?
As a first time visitor, the best areas to stay in Chicago would be either near the Magnificent Mile or in the Loop. Other great areas to stay in Chicago include West Loop and Gold Coast.
The reason I suggest these two areas is because of the access to restaurants, museums, and other attractions. You can walk easily from place to place or take a local bus to get around. There are also a lot of accommodation options in these two touristy areas.
The Magnificent Mile
There are a ton of hotels near on Michigan Avenue as well as between Dearborn St. and Michigan Avenue.
The Loop is a vibrant area where you will find the Bean at Millennium Park and all the famous museums in Chicago. You will inevitably spend a lot of time in the Loop area, so it’s a good area to stay.
West Loop & Fulton Market
If you want to stay somewhere close to good food, then you should consider Fulton Market and West Loop, an area west of the Loop. Formerly known as the meat-packing district, the West Loop is super walkable with industrial aesthetics and amazing restaurants.
In fact West Loop is one of my favorite areas in Chicago. I went there a few nights in a row just to try different restaurants and coffee shops.
So if you don’t mind walking or taking the bus to get around Chicago, then consider staying in the West Loop.
If West Loop is my 2nd favorite area in Chicago, then Gold Coast is my absolutely favorite area in Chicago.
Gold Coast is north of the Loop and it is one of the most luxurious neighborhoods in Chicago. It is the home of beautiful mansions (like the original Playboy Mansion), upscale restaurants and stores (like RH).
You can easily walk to the beach and Lincoln Park and it is a short ride down to the Loop.
Long Weekend (3 Day) Chicago Itinerary (With Maps)
Now you know some of the basics of how to get around and where to stay in Chicago, let’s talk about what you will actually do (and eat) in Chicago for a long weekend!
I am just so excited for you. Really, Chicago is such a nice place to visit when the weather is good (yeah don’t visit in the winter). With Lake Michigan to the east and tons of parks to relax and explore, Chicago really is beautiful when the weather is warm.
Coming from New York City, I am just so impressed with how clean and neat Chicago is and it also is not super crowded compared to New York City. So if you want a taste of Chicago as a first time visitor, you will love all the suggestions on this itinerary.
For your convenience, I mapped out all the major attractions and awesome restaurants in Chicago on this map below.
Day 1: Famous Museums in the Loop + Skydeck (Orange Pins)
Day 2: Art Museum, Parks, Architectural Tour, 360 CHICAGO (Purple Pins)
Day 3: Magnificent Mile, Near North Side, Lincoln Park area (Green Pins)
Where to Eat: Red pins
Day 1 in Chicago: Museums + Skydeck
Start your first day in Chicago with a bang! You will see some of the best museums in Chicago in what’s known as the Museum Campus.
Museum Campus is in the southern end of the Loop; it is an area that houses 3 of the most famous museums in Chicago: Adler Planetarium, Shedd Aquarium, and Field Museum.
It is also a beautiful area to walk around, with plenty of greens (and parks) and the view of Chicago skyline and Lake Michigan.
All 3 museums open at 9am, but I would actually recommend going to Shedd Aquarium first because it gets really crowded with school tours and just kids running around especially during the summer months.
So we will start our 3 day Chicago itinerary with Shedd Aquarium.
Hours of Operations: 9am – 9pm
Ticket Price: $42-$45 (if not Chicago resident) with tax
Time Needed: 2-3 hours at least
Shedd Aquarium is one of the largest and most renowned aquariums in the US.
It houses an impressive collection of marine life from around the globe. It features diverse exhibits that showcase a wide range of aquatic creatures, including fish, sharks, dolphins, sea turtles, penguins, and more. In fact it has over 32,000 animals representing 1,500 species; that number is just mind blowing to me.
One of the highlights of Shedd Aquarium is the Oceanarium, a massive exhibit that replicates a Pacific Northwest coastal environment. Here, visitors can observe majestic beluga whales, playful dolphins, sea otters, and a variety of marine birds as they interact.
Funny story here: I was watching the “Animal Spotlights” program with the beluga whales when I visited. After the show finished as I was walking out, the beluga whales swam very close to me and jumped out of the water. Of course I couldn’t miss the opportunity to take photos of it. Little did I know he came over to splash me, so as you can imagine, I got super wet after taking that photo.
There are also other activities such as penguin encounters which require additional ticket.
Overall, if you want to avoid the crowd it’s best to visit Shedd Aquarium right at opening.
Hours of Operations: 9am – 9pm (9am – 10pm on Wednesdays)
Ticket Price: $35 (entry + 2 shows)
Time Needed: 2-3 hours at least if you watch the shows
Adler Planetarium is the first planetarium in the western hemisphere!
At Adler Planetarium, you can explore the wonders of the universe, learn about space science, and engage in immersive experience.
Adler Planetarium is perfect if you have kids traveling with you. Depending on the ticket you get, you can watch 1 or 2 planetarium shows.
The reason I suggest going to Adler Planetarium after Shedd Aquarium is that many shows are in the early afternoon, so if you arrive at 9am when they open you will need to wait a long time before showtime.
The Field Museum is a renowned natural history museum that lets you explore the wonders of our planet and its history.
It has a vast collection of artifacts, specimens, and interactive exhibits as well as special temporary exhibits.
The Field Museum is home to an extensive range of exhibits that cover a wide array of topics, including anthropology, paleontology, geology, biology, and more. One of the museum’s most famous and beloved attractions is Sue, the largest and most complete Tyrannosaurus rex fossil ever discovered.
The museum also showcases exhibits that delve into human cultures and civilizations from around the globe, from ancient Egyptian mummies and artifacts to Native American artifacts and cultural displays.
I forgot to mention that you can eat at the cafes inside the museums or planetarium or walk 10 minutes to get Chicago hot dogs at Devil Dawg (or eat at other restaurants).
Skydeck is an iconic observation deck in Chicago. It was formerly known as the Sears Tower and now known as Willis Tower (the naming right will change in a few years so it might be called something else).
The Skydeck is situated on the 103rd floor of the Willis Tower, making it one of the highest observation decks in the United States. It offers unparalleled panoramic views of the Chicago skyline, Lake Michigan, and the surrounding area.
On clear days, you can see for miles, taking in the beauty of the city’s architecture and the vastness of the landscape.
The most famous feature at Skydeck is “The Ledge”, which are 4 glass bottom “boxes” that extend out from the building. You can step onto the transparent surface suspended over 1300 feet in the air.
If you have a fear of heights like I am, you might get scared standing on it.
For different sized parties, there is a different time limit. For a party of 1-3 people, you have 1 minute to take photos/ videos after the official photos finish (they have cameras latched above the ledge to take photos of you and sell you the pictures).
For parties of 4 or more you get 90 seconds. The attendant will set an alarm and can help you take photos if you are traveling alone.
I highly recommend going to Skydeck around sunset time so you can see the colorful sky as well as all the lights come on in the city. So if you finished your museums early you can grab dinner first then go to Skydeck for sunset.
Day 2 in Chicago: Art Museum, Parks, Architectural Tour, 360 CHICAGO
After a whole day of touring the most famous museums in Chicago, you will spend day 2 doing a variety of things. This is going to be an action packed day so be prepared to walk.
Start your second day in Chicago by checking out the Bean and Crown Fountain for some photos. Proceed to walk through Millennium Park and Grant Park before heading back to the Art Institute of Chicago to see world famous artwork.
If time allows, stop by the Chicago Cultural Center for a quick (and free) self-guided tour to see the beautiful ceilings before heading back north to the Chicago River for a fun and educational architectural cruise. Finish your evening at 360 CHICAGO for another amazing view of Chicago at sunset.
The Bean and Crown Fountain at Millennium Park
The Bean, officially known as the Cloud Gate, is one of the most iconic symbols of Chicago. Located in Millennium Park (which is in Grant Park), it is a must-see attraction for all first-time visitors.
Designed by renowned British artist Anish Kapoor, the Bean is a massive, highly polished stainless steel sculpture that reflects and distorts the surrounding cityscape.
You can walk around and under the sculpture and take some artistic photos with it. But be warned that the bean does get crowded so if you want an instagram worthy photo you will have to go fairly early.
Close to the Bean is another famous art installation called Crown Fountain.
Designed by Spanish artist Jaume Plensa, the fountain consists of two towering glass block towers facing each other across a shallow reflecting pool. The fountain uses digital technology within the glass block towers to display the ever-changing faces of Chicago residents.
Millennium Park & Grant Park
Chicago has no shortage of parks, in fact public parks make up around 9% of total Chicago land (according to my architectural guide).
During your second day in Chicago you will get a chance to see two of the most famous parks in Chicago, Millennium Park and Grant Park. Millennium Park is technically inside Grant Park.
The Bean and Crown Fountain are in Millennium Park, so you have already seen part of the park. As you explore the park, you will see some other highlights, such as the Jay Pritzker Pavilion, an outdoor concert venue, Lurie Garden, a tranquil oasis in the middle of Millennium Park, and the BP Pedestrian Bridge, a famous stainless steel bridge that connects Millennium Park with Maggie Daley Park.
As you continue to walk south, you will actually pass by The Art Institute of Chicago (we will go back to that in a second) and arrive at Grant Park.
Grant Park is often known as “Chicago’s front yard”.
Grant Park is right next to Lake Michigan, so you have an incredible view of the waterfront and the Chicago skyline.
Within Grant Park, you’ll find several notable landmarks and attractions. Buckingham Fountain, one of the park’s most iconic features, serves as a grand centerpiece with its majestic water displays and ornate design.
Other landmarks in Grant Park include MAGMA, an art installation, the Turtle Boy, Dove Girl, Fisher Boy and Crane Girl fountains, a farm and rose gardens.
Art Institute of Chicago (Closed Tue & Wed)
The Art Institute of Chicago is a world-renowned art museum and cultural institution. Founded in 1879, it is one of the oldest and largest art museums in the US.
There are over 300,000 works of art in the Art Institute’s collection, from ancient Egyptian artifacts to European and Asian masterpieces to contemporary arts and photography.
The collection features renowned works by legendary artists such as Vincent van Gogh, Pablo Picasso, Claude Monet, Georgia O’Keeffe, and Grant Wood, among many others.
There are also temporary special exhibitions featured at the Art Institute that cost additional $10.
Chicago Cultural Center
Hours of Operations: 10am – 5pm
Ticket Price: Free!
Time Needed: 30 min – 1 hour
The Chicago Cultural Center is in a beautiful historical building right across from the Bean.
Originally built in 1897 as the city’s first central public library, the Chicago Cultural Center is a stunning example of Beaux-Arts architecture. The building itself is a work of art, featuring grand marble staircases, intricately designed mosaics, and ornate decorative elements.
There are 2 beautiful stained glass domes in the Cultural Center and an art gallery. There are also cultural events and programs that are hosted at the Cultural Center regularly.
Chicago Architectural Cruise
Led by knowledgeable guides, the architectural cruise tours offer fascinating insights into Chicago’s rich architectural history and the visionary architects who shaped the city. You’ll learn about the different architectural styles, from Beaux-Arts to Art Deco to modernist designs, and how they contribute to the unique character of Chicago’s skyline.
360 CHICAGO, formerly known as the John Hancock Observatory is one of the two popular observation decks in Chicago.
Located on the 94th floor of this iconic building, it offers breathtaking panoramic views of the city’s skyline and Lake Michigan.
The main highlight of 360 CHICAGO is its observation deck, which provides visitors with an unparalleled 360-degree view of the cityscape.
One of the unique features of 360 CHICAGO is the TILT experience. This exhilarating attraction allows you to step into a glass-enclosed moving platform that tilts outward from the building, giving you a thrilling downward-facing perspective of the city below.
There is also a bar and some seating areas at 360 CHICAGO so you can relax while enjoying the view.
I visited during sunset and I thought the view was amazing. This is why I suggest going to 360 CHICAGO before sunset time so you can grab an early dinner before visiting.
Day 3 in Chicago: Magnificent Mile, Lincoln Park, Navy Pier, Food Tour
Your last day in Chicago is pretty chill. You have the option to do everything or just chill, eat, shop or check out some other museums.
You can start your day at the Starbucks Reserve Roastery to grab some coffee and pastries before window shopping on the Magnificent Mile to do some shopping (or window shopping). If you are visiting on a Friday or Saturday, you can do a tour inside the magnificent Chicago Theatre. If not, wander on the Riverwalk and take in all that Chicago has to offer.
Get lunch then take the bus over to Lincoln Park where you can check out the free Lincoln Park Zoo and Conservatory. Finish your day by having some fun at Navy Pier, check out the West Loop area for great food or have a fun night at a comedy club.
Starbucks Reserve Roastery
Hours of Operations: 8am to 8pm M-Th; 8am to 9:30pm Fri – Sun
Located on the magnificent mile, the Chicago Starbucks Reserve Roastery is a fantastic place to stop by for some coffee and pastry early in the morning.
This is no ordinary Starbucks Reserve, in fact this particular location is the largest Starbucks in the world. It has 5 stories and each story has something different.
It also offers a bakery with a wide selection of freshly baked goods, artisanal bread, and delicious pastries.
The Magnificent Mile, often referred to as “Mag Mile,” is a world-famous stretch of North Michigan Avenue. It is renowned for its upscale shopping and beautiful architecture.
Stretching for approximately one mile, the Magnificent Mile is lined with a dazzling array of high-end boutiques, department stores, luxury brands, and flagship stores of renowned fashion designers. You can find brands like Burberry, Cartier, Rolex on Michigan Avenue.
Aside from shopping, the Magnificent Mile is also home to a plethora of renowned landmarks and architectural gems such as the Wrigley Building, the Tribute Tower, the John Hancock Center (where 360 CHICAGO is), and the Chicago Water Tower.
You will also see street performers, Architectural Cruise ticket booths, Chicago Riverwalk, theaters, and Museum of Ice Cream on the Mag Mile.
The Chicago Theatre
The Chicago Theatre is a famous landmark in downtown Chicago.
Built in 1921, this theater is known for its grandeur, architectural beauty and its significance in Chicago’s cultural and entertainment scene.
If you are not watching a show in the theater, your only option to visit the inside of this magnificent building is to do the Marquee Tour.
The tour will lead you inside to see the grand lobby, sweeping staircase and beautiful auditorium. You will get a chance to stand on the stage and learn about the history of the building.
If you are not doing the Chicago Theater Marquee Tour don’t worry, you can either spend more time shopping or check out the Chicago Riverwalk.
The Chicago Riverwalk is a scenic and vibrant promenade that runs along the south bank of the Chicago River. It stretches for 1.25 miles and you can stroll, relax, dine, and enjoy the stunning views of the city’s iconic architecture.
Lincoln Park Zoo
Located at Lincoln Park, the zoo is one of the oldest zoos in the US and it is completely free to visit!
Spanning over 35 acres, the Lincoln Park Zoo is home to a diverse collection of animals, from gorillas to lions to exotic birds and reptiles.
The Farm-in-the-Zoo is a popular attraction where children can interact with farm animals, learn about agriculture, and engage in hands-on activities.
Lincoln Park Conservatory (Closed Monday and Tuesdays)
Located right next to the Lincoln Park Zoo, the conservatory is a hidden gem that should not be missed.
The conservatory, built in the late 1800s, showcases an impressive collection of tropical plants, flowers, and trees from around the world. As you step inside, you’ll be greeted by a lush and vibrant environment, with soaring palm trees, colorful blooms, and cascading vines that create a truly enchanting atmosphere.
The conservatory is divided into several distinct rooms, each with its own unique theme and plant life. The rooms include the Palm house, the Fern Room, the Orchid Room and the Show House.
If you are visiting the zoo you should definitely stop by the conservatory and enjoy the tranquility from the bustling city.
After an eventful day, you can either stop by Navy Pier to check out the Centennial Wheel, the ferris wheel that can be seen from all the observation decks and cruise tours or go to the West Loop to eat at some of the most iconic restaurants in Chicago.
If you are into comedy shows, Chicago also has a number of comedy clubs such as The Comedy Bar, the Comedy Clubhouse, Zanies Comedy Night Club and many others.
Is 3 Days Enough For Chicago?
3 Days in Chicago is the perfect amount time for a first time visitor to see the highlights of Chicago.
From world class museums to renowned restaurants to beautiful parks, you can see the best of Chicago over a long weekend (3 days) in Chicago.
Of course you can always spend more time in Chicago to explore things a little further away from city center, such as Garfield Park Conservatory, the largest conservatory in the US, relax on a beach, check out Hyde Park and the Museum of Science and Industry, explore the trendy area of Wicker Park, or venture out to the beautiful Baha’i temple or the magnificent Hindu Temple of BAPS Shri Swaminarayan Mandir.
How to get to Chicago?
Unless you are traveling from nearby cities, most likely you will have to fly to Chicago.
Chicago is served by two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW).
O’Hare International Airport, located about 17 miles northwest of downtown Chicago, is one of the busiest airports in the world and serves as a major hub for domestic and international flights.
Midway International Airport, situated about 10 miles southwest of downtown Chicago, primarily serves domestic flights and is known for its convenient location and smaller size compared to O’Hare. There are only a number of airlines that fly to Midway International Airport, such as Allegiant, Avelo, Delta, Frontier, Porter, Southwest and Volaris.
Besides flying, you can take the Amtrak train to Chicago to Union Station or take a long distance bus such as Greyhound to Chicago. Union Station, the city’s major train station, often serves as a hub for various bus services as well.
How to get around Chicago?
You can use a combination of public transportation, biking, walking and ride share apps to get around Chicago during your long weekend Chicago trip.
Chicago is a super walkable city if you are planning to stay in the downtown area and do touristy things! You can literally walk from museum to museum or just walk along Michigan Avenue.
I walked A LOT when I was in Chicago and when I got tired, I used other forms of transportation below.
Public Transportation in Chicago
Public transportation in Chicago includes the “L” (or the CTA trains), buses and the Metra Rail.
The CTA train, otherwise known as the “L” (short for “elevated”) is a convenient way to get around the city with over 140 stations located throughout Chicago and the surrounding areas.
The “L” has 8 lines, known by their colors (Blue Line, Red Line, Green Line, etc). The Blue Line and Red Line run 24 hours.
I was super confused when I was looking up directions in Chicago because some blogs would say take the “L” train but Google Maps was telling me to take the Blue Line and the airport sign says “CTA trains”. Well I am here to tell you that they all mean the same thing. L = CTA trains = whatever color Line.
The bus network is also expansive, with 129 bus routes covering places that may not necessarily be served by the L.
Navigating & Paying for the public transportation station in Chicago
Google Maps and City Mapper both work well in Chicago when looking up directions with public transportation. You can also download the Ventra App which shows you public transportation information.
Paying for public transportation in Chicago is easy and there are a lot of options.
Apple Pay/ Google Pay/ Contactless Cards can be used to pay for the bus and L trains. You just have to tap your card and you are good to go. However I did notice that using contactless cards on buses costed me $5 for the full price (instead of $2.25) the first time I used it on a bus.
Ventra App: The Ventra App allows you to load money into the app and add the Ventra card to Apple Pay and Google Pay, then you can tap and pay on buses and L trains. I used this in Chicago and the bus fare was the $2.25 fare.
CTA/Pace Pass: You can purchase a 1, 3, 7, or 30 day CTA/ Pace Pass from either the ticket machine or load onto your Ventra account.
Taking Uber/ Lyft in Chicago
Uber and Lyft both operate in Chicago and you can easily get a car when it is too late or you simply do not want to bother with public transportation.
While I was in Chicago, I found Lyft to be a lot cheaper than Uber and the cars came faster. You may have a different experience but check both apps.
Biking in Chicago
When I was in Chicago I saw public bikes called Divvy Bikes all over Chicago.
You can buy a Pass from Divvy, find an available bike, unlock the bike and take short rides. In fact Lyft operates the Divvy system in Chicago. When you look for cars on Lyft, you can actually see options for Divvy bikes.
Hop-on-hop-off bus in Chicago
If you just want to go to the main attractions in Chicago then a hop on hop off bus may be worth it.
Where to Eat in Chicago
Chicago is a food lover’s paradise, with a vibrant culinary scene that offers a diverse range of dining options. Whether you’re craving deep-dish pizza, sizzling steaks, ethnic cuisine, or innovative fine dining, the city has something to satisfy every palate.
If you are in Chicago you probably want to try the iconic Chicago hotdog, deep dish pizza, and Italian beef sandwiches.
For Chicago hot dogs, I would recommend Superdawg Drive-in, the Wiener’s Circle, Portillo’s and Devil Dawg.
For deep dish pizza, the three most famous places are Lou Malnati’s Pizzeria, Giordano’s, and Pequod’s Pizza.
When it comes to Italian beef sandwiches, be sure to check out Portillo’s or Al’s Italian Beef.
There are just so many amazing and famous restaurants in Chicago that I can’t list them all. Some of the most noteworthy restaurants include Alinea, Girl & the Goat, Au Cheval, XOCO, Grand Lux Cafe, and the Purple Pig. If you want a really beautiful restaurant then head to the RH store and eat in their 3 Arts Club Cafe (super overpriced though!).
I bookmarked all of these restaurants (and more) on my Google Maps above. You should definitely aim to get reservation at least 2 weeks in advance for many of these restaurants (except Alinea, that’s a whole different story).
Saving Money on Chicago Attractions
If you are planning to visit all the major attractions in Chicago, then the best way to save money is to get one of the Chicago discounted attraction passes.
The individual attractions do cost between $30 – $50, and they add up to quite a lot of money if you want to see all the famous ones.
With these Chicago discount passes you pay upfront for the pass then you can visit the available attractions for free (within a particular time period or with a particular number of attractions).
Other ways to save money in Chicago is to take public transportation and walk instead of taking Uber everywhere unless it’s late night.
Like this post? Pin this 3 day Chicago itinerary to Pinterest!