My 5-Day Chicago Itinerary

Welcome to my 5-day itinerary for Chicago!

Despite being called the “Second City”, Chicago is known for many “firsts”, including the world’s first skyscraper, the first Ferris wheel, first brownie… the list goes on and on. The city has accomplished many other incredible feats throughout its rich history, like reversing the entire flow of its river and rebuilding from virtually nothing, turning the city into a huge hub for architecture.

While 3 days might be enough to visit all of the main tourist sights, there is so much to see and do in Chicago outside of downtown. As a current resident, I’m constantly discovering new things to check out. So, I wanted to share some of the top things to do as well as some hidden gems that you can pack into 5 days.

Read: Top 10 Things to Do in Chicago

This is a jam-packed itinerary, so feel free to adjust this to fit your needs and preferred pace. I’ve also included recommended areas to stay as well as additional activities and restaurants to try out if you have more time or want other options.

I hope you enjoy your time in this magnificent city.

Daily Itinerary

Day 1: The Loop

1. Millennium Park

Pritzker Pavilion in Millennium Park

A great way to kick off your trip to Chicago is to visit one of the top tourist attractions in the city: Millennium Park. This is easy to walk to if you’re staying at an accommodation downtown.

Famously home to The Bean, Millennium Park is visited by up to 25 million people a year. Here you’ll also find Pritzker Pavilion, Lurie Garden, and Crown Fountain. If you have time, take a brief walk on the bridge over Columbus Drive to Maggie Daley Park, where you’ll find a skating ribbon, climbing wall, mini golf, tennis courts, and a huge children’s play garden.

Know Before You Go: On some weekends and for events, Millennium Park cracks down on security. During these times you are only able to enter through the two main entrances on Michigan Avenue, and they have a security check point to search for weapons, including pocket knives and pepper spray.

Lurie Garden in Millennium Park

The Main Attractions:

  • The Bean
    • Sculpted by artist Anish Kapoor, The Bean’s actual name is the Cloud Gate (though no one actually calls it that). The sculpture is supposed to look like a drop of mercury just before it hits the ground. Made up of 168 stainless steel panels, The Bean weighs around 110 tons
  • Jay Pritzker Pavilion
    • Designed by Frank Gehry, this pavilion is an outdoor performance venue that hosts events throughout the summer, such as movie nights and concerts. Frank Gehry also designed the Walt Disney Concert Hall in Los Angeles and the Guggenheim Museum in New York
  • Lurie Garden
    • Considered a “naturalistic” garden, Lurie Garden is a mini escape from the bustling city where you’ll also find great views of the skyline
  • Crown Fountain
    • Designed by Jaume Plensa, an artist from Barcelona, this fountain is unlike any fountain you’ve seen before—it consists of two 50-ft brick-like structures that stand opposite each other in a plaza. Built-in LED panels display a slow cycle of faces of over 1,000 Chicagoans that smile at you, and then spit on you
    • The design was meant to imitate fountains with animals spitting out water, and it’s a popular place for kids to play during the hot summer months

Other Park Facts:

  • This 24-acre park is the largest green roof in the western hemisphere. Underneath you’ll find a parking garage, part of the underground Chicago pedway, and a Metra rail line
  • The park was supposed to open in 2000 to celebrate the millennium, but due to numerous additions to the original plan, it didn’t open until 2004
  • Originally, Millennium Park was supposed to cost around $150 million, but with additions such as Pritzker Pavilion, the park ended up costing close to $490 million

Read: 7 Facts About Chicago You Probably Didn’t Know

2. Lunch: Deep Dish Pizza at Lou Malnati’s

Deep dish pizza is a crucial part of Chicago’s food culture, so it’s a must-try for any first-time visitors to the city. This pie-like pizza is said to have originated at Pizzeria Uno in 1943, but one of the best chains is Lou Malnati’s, which you can find all throughout the city.

Deep dish takes around 45-50 minutes to make after you order it, and wait times for any deep dish pizza place are usually pretty long around dinner time, so it’s best to go during lunch. If you want a guaranteed table, make sure to make a reservation in advance.

Lou Malnati’s first opened in the suburb of Lincolnwood on St. Patrick’s Day in 1971, and today it has over 60 locations in the Chicagoland area. What makes Lou’s pizza unique from other deep dish places is its light butter crust and chunky, fresh tomato sauce. Lou’s salad is also highly rated.

3. Art Institute of Chicago

“Paris Street on a Rainy Day” by Gustave Caillebotte in the Art Institute

The Art Institute is personally my favorite museum in Chicago. With more than 300,000 pieces of art in its permanent collection, the museum is home to numerous famous works, including Van Gogh’s Self-Portrait, A Sunday on La Grande Jatte by Georges Seurat, Nighthawks, American Gothic, and over a dozen Monet pieces.

Though, one of the most iconic parts of the museum is its Miniature Rooms exhibit, which features an array of intricate tiny models ranging from a lavish 1700s French living room to a rustic Massachusetts kitchen from the 17th century.

An up-close view of one of the miniature rooms in the Art Institute

Plan to spend at least two hours at this museum to browse the dozens of permanent and temporary exhibits, though you would need to dedicate a day or more to see everything on display.

  • Tickets: $32/adult
  • Hours: Thursday, 11am-8pm; Friday-Monday, 11am-5pm; closed Tuesday & Wednesday
  • Website

4. Dinner: LondonHouse Rooftop

The LondonHouse Rooftop is situated right beside the Chicago River, offering scenic views over the waterway and of the surrounding skyline. Here you can indulge in specialty cocktails along with an elevated dinner to end the night.

Day 2: Streeterville, Navy Pier, Magnificent Mile

1. Breakfast: Wildberry Pancakes and Cafe

Wildberry is a popular breakfast/brunch restaurant with two locations in downtown Chicago. The menu features classic breakfast foods and specialty pancakes. Be aware that the restaurant can be very busy, especially on the weekends, so arrive early or book a reservation in advance.

2. Architecture Boat Tour

Embarking on an architecture boat tour is the #1 must-do activity in Chicago. Not only do you get to relax on the Chicago River and admire beautiful, iconic buildings, but you also get to learn about how Chicago began and how it became the Second City we know it as today. Chicago would be nothing without its architects/engineers and the unique buildings we have because of their ingenuity.

There are quite a few companies that offer boat tours, but here are the top 3:

  • Shoreline Sightseeing
    • 75-minute tour
    • $49.95/adult
    • Can board from Michigan Avenue or Navy Pier
    • Website
  • Wendella Tours & Cruises
    • 90-minute tour
    • $44/adult
    • Boards at Michigan Avenue
    • Website
  • Chicago Architecture Center

Know Before You Go: Even in the summer, it can get a little chilly and windy on river, so dress appropriately! Also be sure to arrive at least 15 minutes prior to departure. If you’re visiting during winter and think it will be too cold, opt for an interior architecture walking tour!

3. Navy Pier

As one of Chicago’s top tourist attractions, Navy Pier has a plethora of things to do for people of all ages. The pier itself is free to enter, but it’s worth it to pay for some of the attractions here:

Pier Park /Centennial Wheel

The Pier Park is a small amusement area that includes a Ferris Wheel, carousel, drop tower, wave swinger, tea cups, and more. All are extra paid experiences. At 196ft tall, the Centennial Wheel is the highlight of the park and gives visitors excellent 360-degree views of Chicago and Lake Michigan. The carts are enclosed, so the ride can be enjoyed any time of the year.

  • Centennial Wheel Tickets: $18/adult
  • Website

Flyover Chicago

This attraction is basically what the name implies: a fly over Chicago. This is a perfect, immersive way to experience Chicago within only 30 minutes. If you’ve ever been to Soarin’ at Disney’s Epcot, that’s basically what this is.

Flyover takes place in a planetarium-like domed theatre with 3 levels of seating that can fit up to 61 people at a time. You’re suspended about 20 feet in the air, and the seats move in such a way that it really feels like you’re flying over Chicago. The show features stunning drone footage and incredible music/audio, along with other immersive elements like wind and spritzes of water as you fly over the river and lake.

  • Tickets: $33.95/adult
  • Hours: Sunday-Thursday, 11am-9pm; Friday & Saturday, 11am-10pm
  • Website

Know Before You Go: If you get motion sick easily, this might not be the best experience for you.

Children’s Museum

This fun, interactive museum is perfect for children of all ages, including young kids. The museum also offers various activities and seasonal events, such as crafts in the Art Studio and dance parties. Many activities are educational, inviting kids to learn about fire safety, figure out how to solve problems, and discover skills related to STEAM (science, technology, engineering, art, and math).

  • Tickets: $21/person, including children (those under 1 are free)
  • Website

Chicago Shakespeare Theater

If you’re looking for excellent theatre, the Chicago Shakespeare Theater is a great place to go. The venue doesn’t solely perform Shakespearean shows. Be sure to see what’s playing during your visit here: Website

Dining/drinking:

  • Food Court
  • Giordano’s
  • Harry Caray’s Tavern
  • Margaritaville
  • Offshore Rooftop
  • Beer Garden

Know Before You Go: If you’re visiting Chicago between Memorial Day and Labor Day, be sure to also check out the firework show! The fireworks can be viewed anywhere along the lakeshore, as long as the pier is in view. Shows start at 9pm on Wednesday and 10pm on Saturday.

Map

4. Magnificent Mile

The #1 shopping district in Chicago, the Magnificent Mile is another must-visit area to explore. Mag Mile stretches from Oak Street to the Chicago River along Michigan Avenue and consists of luxury stores, the Water Tower Place, Starbucks Reserve Roastery (the biggest Starbucks in the world), as well as iconic historical structures like the Water Tower, Wrigley Building, and the Tribune Tower. Spend a couple hours here perusing the shops and taking in the architecture.

5. Dinner: Ed Debevic’s

If you’re looking for a unique, fun dining experience, you need to go to Ed Debevic’s. Their whole schtick is to be snarky to customers, which is quite an entertaining experience. You might even catch the staff dancing on tables and putting on a little show. The restaurant itself is themed like a 50s diner and features classic diner foods like pancakes and burgers.

6. 360 CHICAGO at the Hancock Building

View from the Hancock Building looking north at night

What better way to end your day than to see a stunning view of Chicago’s glittering cityscape at night?

At more than 1,000-ft above Chicago’s streets, you’ll experience breathtaking, 360-degree views of Chicago and Lake Michigan from the Hancock Building’s 94th floor. I personally prefer the view from the Hancock Building more than from the Willis Tower Skydeck because of its proximity to the expansive lake.

If you want to add a bit of thrill to your visit, you can add the TILT experience for an extra $10 to tilt 30 degrees over the side of the building. The experience only lasts about 2 minutes and I honestly I don’t think it’s worth $10, but it’s an option if you’re interested.

You can also visit the Cloud Bar to sip on a cocktail while taking in some of the best views of the city.

  • Tickets: $30-53/adult. Prices vary depending on the time of year and day. Prices also depend on the package you book
  • Website

Day 3: Lincoln Park

1. Breakfast: Blue Door Farm Stand

Heading up to Lincoln Park for the day, you’ll start your morning at one of my favorite brunch spots, the Blue Door Farm Stand. Blue Door has a very cozy, clean atmosphere. Small details like wood accents and blue floral plates add a rustic appeal. The food is also delicious, with unique omelets, breakfast wraps, and salads.

2. Lincoln Park Zoo

After breakfast, head over to the free Lincoln Park Zoo (opens at 10am). See animals such as giraffes, kangaroos, penguins, birds, seals, and so so many more, including the highly beloved lion pride. Most people spend about 1-2 hours here.

After your visit to the zoo, stop by the Lincoln Park Conservatory and take in the beautiful botanical gardens (also free, but still requires a reservation in advance), as well as the Alfred Caldwell Lily Pool around the corner.

3. Lunch: Weiner’s Circle

After the zoo, refuel with an iconic Chicago hot dog at one of the best hot dog stands in the city: Weiner’s Circle. The staff is pretty tame during the day, but like Ed Debevic’s, their whole shtick is to be rude to customers, especially in the evening. Though, unlike Ed Debevic’s, this would not be a child-friendly place at night because the language gets a little more vulgar. But it’s all in good fun! Just don’t ask for ketchup. It’s a memorable experience for sure.

If you’ve never had a Chicago hot dog, it consists of yellow mustard, white onions, tomatoes, relish, pickles, sport peppers, and a dash of celery salt, typically on a poppy seed bun. I personally don’t like most of the ingredients individually, but together they somehow work. It’s very delicious (and a little spicy)!

4. Belmont Harbor/Lakefront Trail

Chicago is incredibly unique, but what really sets it apart from other US cities is that it’s right beside a huge freshwater lake, providing a great escape from the traffic-heavy city.

After you indulge in your hot dog and maybe a sweet treat nearby (try boba at Uni Uni or get some ice cream at Taiyaki next door), head east through Lincoln Park to Belmont Harbor where you can go for a relaxing stroll along Lake Michigan on the concrete beach. This is personally one of my favorite things to do on a nice day because of how scenic and peaceful it usually is.

If you want to walk farther, continue your stroll along the Lakefront Trail. This path extends 18.5 miles along Chicago’s shoreline. Instead of taking the bus back downtown, you could rent a Divvy Bike and cycle about 4 miles south on the trail. Stop and take in the view from one of the numerous sandy beaches along the way.

5. Dinner: Del Seoul

Also located in Lincoln Park, Del Seoul blends “the Korean street foods of California, Asia, and Korea”, putting a unique twist on classic Korea food. Sample Korean BBQ tacos, Korean banh mi sandwiches, and delicious bentos.

6. Second City

End the night by seeing a comedy show at the famed Second City, where actors such as Catherine O’Hara, Steve Carell, and Keegan-Michael Key got their starts in comedy. Second City has a handful of theaters for both mainstage shows and student showcases. You’ll find a wide variety of productions playing throughout the year, with a mix of improv and sketch shows. Whichever show you choose, it will be a completely unique experience.

See what’s playing here.

Day 4: Museum Campus, The Loop

1. Breakfast: Yolk

Yolk has 6 locations in downtown Chicago and offers classic breakfast dishes in a bright, urban setting. The breakfast menu features seasonal beverages, fan favorite breakfast sandwiches, French toast, and benedicts with house made hollandaise.

2. Field Museum

Located on Museum Campus, the Field Museum is one of the top museums to visit in Chicago. This natural history museum features around 40 million artifacts and specimens from both the natural world and human history, meaning you could spend hours upon hours taking in the exhibits. However, most people spend 3-4 hours here.

A few of the many exhibits include:

  • Griffin Halls of Evolving Planet – Explores the history of the earth, featuring fossils and dinosaur skeletons, most notably Sue the T-Rex
  • Africa – Features a large collection of artifacts and displays that highlight various parts of Africa and its history
  • Grainier Hall of Gems – Consists of 600+ gemstones, including raw gems and jewelry

Many of the artifacts first came to Chicago in 1893 to be temporarily displayed at the World’s Colombian Exposition, and in 1921 the current Field Museum (named after the prominent late-1800s Chicago businessman, Marshall Field) was built to permanently house these artifacts.

  • Tickets start at $30/adult
  • Hours: 9-5pm daily
  • Website

3. Lunch on Museum Campus

There are multiple food options around museum campus, including a cafe in the Field Museum, food stalls around the campus, and a cafeteria at the next stop, Shedd Aquarium. Tacos from one of the outdoor stalls are definitely a tasty move after a long morning at the museum.

4. Shedd Aquarium

Next door to the Field Museum, Shedd Aquarium features around 32,000 aquatic animals, including dolphins, penguins, beluga whales, sharks, turtles, dozens of species of fish, and more. When it opened in 1930, it was the largest inland aquarium in the Western Hemisphere (now it’s the 3rd largest). It was also the first aquarium ever to have an inland saltwater collection.

The aquarium also has a stingray exhibit and periodic Animal Spotlights where you can see dolphins showing off their smarts and penguins waddling around.

  • Tickets: Varies depending on the day, starts at $40-50/adult
  • Hours: Sunday-Friday, 9am-5pm; Saturday, 9am-6pm
  • Website

5. Chicago Symphony Orchestra

To end your evening, dress up and enjoy a performance by the Chicago Symphony Orchestra.

The orchestra was founded in 1891 and performs more than 150 concerts a year. Visit their website to see what’s currently playing.

Day 5: Wicker Park, Chinatown

1. Wicker Park

Known for its collection of coffee shops, restaurants, and shopping, the hip Wicker Park neighborhood is the perfect place to spend your last day in Chicago. Most of the things to do are along Milwaukee Avenue, the neighborhood’s main thoroughfare.

I have a guide coming soon that explores Wicker Park as well as other popular neighborhoods, so stay tuned to learn about the best things to do in the area. Here is a quick snippet:

Shopping

  • Myopic Books – This two-story bookshop is covered from floor to ceiling with used books of all sizes and genres. The wooden shelves and floors give the store a simple, rustic character. Combine that with the smell of old, well-loved books, and you have a recipe for a great bookstore
  • Reckless Records – If you’re into music or collecting vinyl, this is the place for you. This store has rows upon rows of records. Maybe you’ve been searching for something specific or obscure—they probably have it
  • Kokorokoko – This is a vintage clothing store, mainly housing 80s, 90s, and y2k fashion (I know, how is y2k vintage already?) You can also find accessories and home furnishings here

Restaurants

  • Antique Taco – Great made-from-scratch tacos with a twist, like spicy chicken with honey yogurt and pork carnitas with avocado and bacon
  • Chengdu Bistro – Specializes in food from the Sichuan province in China, known for its noodle dishes and hand-made dumplings
  • Urbanbelly – Founded by famed chef Bill Kim, this restaurant blends his Korean heritage with his wife’s Puerto Rican background, serving delicious dumplings, Korean fried chicken, and ramen

2. Chinatown

If you still have time in your day after Wicker Park, you need to visit one of my favorite neighborhoods in Chicago: Chinatown.

Just south of downtown, Chinatown is kind of hidden away. But with its dozens of restaurants and shops (and boba), it’s a must-visit area. Again, refer to the upcoming neighborhoods post for a more in-depth guide, but here are some of my favorite restaurants and things to do:

Restaurants

  • Lao Sze Chuan – Get their dry chili chicken. That’s all I’m gonna say
  • Dim Sum: MingHin Cuisine, Triple Crown, or Phoenix Restaurant – These are probably the top three dim sum restaurants in Chinatown, and all offer similar items
  • Happy Lamb Hot Pot – All you can eat! If you’ve never had hot pot, you order 1-2 soup broths that boil in front of you in a communal table pot, and you order different raw meats and vegetables to cook in the soup. Be sure to arrive hungry
  • BBQ King – This Hong Kong Style BBQ restaurant has delicious authentic barbeque, including Peking duck

Other Things to Do

  • Ping Tom Park – Named in honor of a prominent businessman and civic leader in Chicago’s Chinatown, this is a lovely small park along the south branch of the Chicago River with picturesque views of the city skyline. It’s a serene place to rest for a moment or to take a short stroll
  • Chinese American Museum – To learn more about Chinatown’s culture and the history of Chinese Americans in the Midwest, take an hour or two to visit this free museum (they accept donations!)
  • Chinatown Square – This is a two-story outdoor mall with many shops and restaurants (some of which are listed above), but in the center is a plaza surrounded by the 12 Chinese zodiacs and their descriptions. It’s a fun area to look around and see if your zodiac description fits you. In front of the plaza is an intricate mural depicting Chinese in America throughout history

Accommodations

Here are some recommendations for places to stay in different neighborhoods of Chicago.

Please Note: The listed prices are not the most accurate, but I wanted to provide a rough estimate if you’re on a budget or looking for something a upscale. These prices are based on a quick Internet search and will fluctuate throughout the year, especially on weekends and around popular events such as the Chicago Air and Water Show in August and the marathon in October.

The Loop

The most convenient location to stay in Chicago is the center of downtown, otherwise known as the Loop. Staying in the Loop places you close to the main tourist attractions and many public transit options, providing you with easy access to almost anywhere in the city.

The detailed ceiling of the Palmer House Hotel lobby
  • Palmer House (Starts at $180/night) – The lobby of the Palmer House is stunning, and it’s also where the brownie was invented! You can still buy the original brownie in the hotel’s cafe
  • Congress Plaza (Starts at $100/night) – I will warn you, this is considered the “most haunted hotel in Chicago”. If that suits your fancy, great! The hotel is rather old, but it’s one of the most inexpensive options for the location
  • LondonHouse (Starts at $220/night) – This has gorgeous views of the river and has a beautiful rooftop bar
  • H Chicago (Starts at $75/night) – If you’re on a budget, H Chicago is one of the city’s top-rated hostels

River North/Streeterville

Another convenient area is near Magnificent Mile in River North or Streeterville (the two neighborhoods just north of the river/the Loop). This area also puts you close to most attractions and transit, but the accommodations might be a little more expensive.

Wicker Park

I’ve already mentioned this neighborhood and some of the things you can do there in a few hours, but it’s also a great area to find a hotel if you want a quieter and less-touristy place to stay. To get downtown, it’s just a short train ride south (~15 minutes) on the Blue Line.

  • The Robey (Starts at $290/night) – Located in the heart of Wicker Park, this hotel is in one of the neighborhood’s most iconic buildings. Be sure to visit the rooftop bar, The Up Room
  • Wicker Park Inn (Starts at $240/night)
  • Hyatt Place Chicago Wicker Park (Starts at $280/night)
  • Stay 424 Hostel (Starts at $50/night) – If you’re on a budget, this hostel is a great option on the outskirts of Wicker Park

Lincoln Park

One of Chicago’s most iconic neighborhoods, Lincoln Park is known for its large amount of green space and historic institutions such as Second City and Steppenwolf Theatre. This is a great place to be close to the lake, the Lincoln Park Zoo, the Chicago History Museum, and miles of walking paths. In the summer stop by the Green City Market on Wednesdays and Saturdays. Lincoln Park is a short bus ride from downtown.

Lakeview

Lakeview is a cozy residential neighborhood just north of Lincoln Park with many artsy shops and tasty restaurants. Its proximity to Lake Michigan provides a relaxing and scenic place to take a stroll. You can get downtown in 20-40 minutes by taking the Red Line south or hopping on a bus.

Safety in Chicago

Chicago is not as unsafe as the media makes it out to be. It’s a big city, so naturally there are going to be incidents here and there with a large population, but you don’t have to be scared walking around. Just use caution and common sense, and be aware of your surroundings at all times, as you would anywhere.

That being said, these are the few places I typically avoid:

  • I usually don’t go south of Chinatown, except if you’re going to the White Sox field or the Museum of Science and Industry. Not all of the South Side is a bad area, but there are certain pockets that have gang activity, and I’m not familiar enough with the area to know where those places are.
  • I try to avoid the trains at night, especially the Red Line. If you’re taking the train before/after a Cubs game, the train will be packed with other baseball-goers and you will be fine. Other than that, I’ve witnessed a few too many instances that have made me uncomfortable riding the Red Line at night as a woman alone. The Green and Pink Lines generally feel more safe though.

In addition, watch for scams in heavy touristy areas, especially on Magnificent Mile and around Millennium Park, but it’s nothing terrible. People will try to hand you stuff—don’t take it. They will likely ask for money. A common scam you will see is men dressed as monks trying to hand you jewelry. Sometimes people will ask for directions and then ask for money. Just avoid eye contact or say, “no thanks” and keep walking.

In fact, I’ve learned the best way to handle these situations is to avoid eye contact and keep walking. You have no obligation to interact with anyone that tries to stop you or ask for something.

All in all, Chicago is a relatively safe place. In fact, Lansing, Minneapolis, Milwaukee, and Nashville are all statistically more “violent” than Chicago, according to World Population Review. Chicago isn’t even in the top 10 of this list.

When to Visit

In my opinion, the best time to visit Chicago is after Labor Day in September through mid-October. Chicago is still very warm through early fall, and once school is back in session the city is a little quieter. Though, June through mid-October is the best time to visit the city in general when the weather is warm. In the summer, expect temps between 70-90° with humidity and 60-75° in spring and fall.

Winter can still be a fun time to visit Chicago—especially during the holidays—but the cold can get pretty brutal. There hasn’t been much snow the past few years, but you definitely need to layer up to explore the city December through March. Expect anything from as high as 50° to -20° during that time, though temperatures usually average at 20-35°.

Guide to Chicago Transportation

With Chicago’s layout being basically a grid, the city’s public transit is pretty easy to navigate—and it’s quite cheap (compared to London and New York).

I recommend utilizing Google Maps to figure out which bus/train you need to take and downloading the Ventra app to find accurate wait times.

The Ventra app also allows you to buy daily passes so you don’t pay per ride. If you plan to use public transit a lot during your trip, this will save you money in the long run.

These are the available passes:

  • 1 Day: $5
  • 3 Days: $15
  • 7 Days: $20
  • 30 Days: $75

Otherwise, you can load money into your account on the Ventra app or simply use a tap-to-pay credit card to scan on the bus or at the train station. A bus fare costs $2.25 and trains cost $2.50. You get 2 additional free rides within 2 hours of your first scan.

Visit the CTA website for information on when specific buses and trains end their routes, as well as for delays and reroutes.

Travel tip! If you don’t want to pay $60+ for an Uber to/from the airport, you can take the train for only $2.50. The Blue Line goes to and from O’Hare, and the Orange Line connects to Midway. Both are about 40-60 minute ride from downtown.

Additional Things to See & Do

If you have more time or want to customize your trip to your preferences, here are some lists of more things to do, places to go, and restaurants to try:

Museums

  • Field Museum of Natural History (listed)
  • Shedd Aquarium (listed)
  • Art Institute of Chicago (listed)
  • Adler Planetarium
  • Griffin Museum of Science and Industry
  • Museum of Contemporary Art
  • Chicago Children’s Museum
  • Museum of Ice Cream
  • Museum of Illusions
  • DuSable Black History Museum
  • Medieval Torture Museum
  • International Museum of Surgical Sciences
  • McCormick Bridgehouse & Chicago River Museum
  • National Museum of Mexican Art
  • American Writers Museum

Downtown Shopping

  • Magnificent Mile (listed)
  • Water Tower Place – Mall filled with a variety of stores like Forever 21 and Free People
  • State Street (in the Loop) – Chicago’s original shopping district. Here you’ll find Macy’s, Primark, Uniqlo, and Nordstrom, among others
  • Oak Street/Gold Coast – A high-end neighborhood with luxury stores such as Prada and Chanel

Theatre/concerts

  • Chicago Symphony Orchestra (listed)
  • Second City (listed)
  • Broadway in Chicago – There are 5 theatres downtown that host national touring productions. See what’s playing during your visit!
  • Drunk Shakespeare

Additional Restaurants

  • Deep Dish Pizza
    • Lou Malnati’s (listed)
    • Pequod’s – Voted the best in Chicago
    • Gino’s East
    • Giordano’s
  • Chicago-style Hot Dogs
    • Weiner’s Circle (listed)
    • Portillo’s
    • Devil Dawgs
  • Italian Beef
    • Al’s #1 Italian Beef – To eat at the original Italian beef shop, visit the location on Taylor Street
    • Mr. Beef – Has recently gained a lot of fame from the TV show “The Bear”
  • Other Iconic Chicago Restaurants
    • Manny’s Deli – Known for its corned beef sandwiches
    • Billy Goat Tavern – A historic bar on the lower level of Michigan Avenue known for its connection to the “Billy Goat Curse” on the Chicago Cubs. Also well-known for its cheeseburgers (thanks to SNL)
    • Girl & The Goat – Famous Stephanie Izard restaurant
    • The Berghoff – German food
    • Gene & Georgetti – Steakhouse
    • Au Cheval – Cheeseburgers and egg-focused entrees
    • The Walnut Room – An iconic, long-standing restaurant in Macy’s on State Street
    • avec – High-end mediterranean restaurant

I could go on and on about everything there is to do and try in Chicago. I haven’t even mentioned Garrett’s Popcorn, tavern-style pizza, all of my favorite bookstores and cafes and activities and…..

Hopefully this itinerary gives you a solid starting point for your trip to Chicago, and fingers crossed I haven’t overwhelmed you with my excitement for this city. Named the “Best City in the U.S.” by Condé Nast Traveler eight years in a row, I wanted to make sure this itinerary truly captures why it’s the best city.

Happy travelling!

Lilly (Happy Lil’ Traveller)

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