Did you know Chicago is the third largest city in North America? Second City is always a good idea. In this ultimate four days in Chicago itinerary you’re going to get the very best of the City including must-see attractions and the best places to go. I think four days in Chicago is the ideal amount of time for a first time visit. 

Chicago is an amazing city filled with culture, vibrance, incredible architecture, banging night life, delicious food (deep-dish pizza), and so much more. Whenever I see the skyline, I honestly feel like Chicago is always welcoming me home. She’s always there, steadfast and strong waiting to welcome you too. 

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How To Get To Chicago

Chicago By Airplane

Chicago has two major airports—Chicago O’Hare International (ORD) and Chicago Midway International Airport (MDW). O’Hare is the biggest airport in Chicago and has won multiple awards for being environmentally conscious. Most travelers fly into Midway because it is closer to the city center. O’Hare is located on the north side and is the perfect place to fly for international trips.

Chicago By Bus

There are several destinations around the US with direct bus routes to Chicago. Greyhound is a great option for taking the bus to Chicago. Click here for Greyhound prices and destinations. You can also get to Chicago by Megabus. They are a budget friendly, city to city service. You can check Megabus destinations and prices here.

Chicago By Train

You can take an Amtrak train straight to Chicago’s iconic Union Station. The station serves both Amtrak and Metra. You can book your Amtrak train tickets to Chicago here. If you’d like to use Metra instead, click here for Metra destinations and prices. 

How To Get Around Chicago

It is very expensive to park anywhere in Chicago. In a city of 2.7 million people, you can expect everyone packed on top of each other. The City is on a perfect grid system making it nearly impossible to get lost. If you get lost, you’re definitely a ding dong.

After the Great Chicago Fire, it was reimagined as the pinnacle of modernity. Here’s a pro tip. Madison Street divides Chicago between north and south, while State Street divides it east and west. The State and Madison intersection in downtown Chicago marks the starting point of Chicago’s grid system.

Chicago Transit Authority (CTA)

This is the second largest public transportation system in the country. The CTA operates Chicago’s eight “L” train lines and 129 bus routes. Locals will call it the “L” because the majority of the train tracks are elevated. There are two lines in Chicago that operate 24/7: the Blue Line, which connects Chicago O’Hare International Airport and downtown, and the Red Line, with service between the North and South Sides via downtown.

Pro tip: Use the reloadable Ventra Card or Unlimited Ride Pass for travel by “L” trains or buses. You can buy these cards at the kiosks at the train stations. Click here to download the Ventra app and make your trip to Chicago a breeze.

Metra Rail

This is a high speed train that serves the Chicagoland area and the greater Chicago suburbs. If you want to go anywhere else around the state, Metra is a good way to go. You can find Metra Rail routes and fares here.

Ride Share & Taxi

You can flag down taxis all around the city. But if you’d like to specifically request a ride you can use CHICABS, ARRO, and CURB. Credit cards are accepted in all taxis.

One of the cheaper ways to get around Chicago is via ride sharing apps like Uber and Lyft.

Chicago Water Taxis

Two of the most popular water taxis are the Chicago Water Taxi by Wendella Boats and the Shoreline Water Taxi by Shoreline Sightseeing. (As a kid, my elementary school would often take us on the Wendella Tours around the city and it was GREAT.) Both companies are great choices for safe and fast ways to get to all the top tourist destinations around the City such as Chinatown, Museum Campus, Willis Tower, Michigan Avenue, Union Station, and Navy Pier. Tours on these Chicago Water Taxis are also included in the Chicago CityPass.

Driving

If you choose to take the plunge and bring your car, here are some apps to help you find the cheapest and best parking around Chicago.

Chicago Cycling on Divvy

There are over 322 kilometers (200 miles) of protected bike lanes around the city. Chicago has a bike-share program called Divvy which offers over 580 stations and 5,800 bikes across the city, available for rent 24/7. Users simply pick up a bike from a self-service docking station and return it to a station near their destination. You can find Divvy locations and rates here. 

Where To Stay in Chicago

Chicago is the third biggest city in the United States. It’s known for culture, food, museums, and amazing architecture. Here are my top seven picks for where you should stay in Chicago. Each neighborhood has its own personality and vibe.

  • Lincoln Park – For budget travelers and families.
  • Wicker Park – Mostly for young people who like trendy cafes and pubs.
  • Gold Coast – For the luxury travelers. 
  • Streeterville – Right across from the Magnificent Mile. Stay here if you’re planning on visiting Navy Pier and the Museum of Contemporary Art.
  • River North – For the luxury travelers, night life lovers, and art enthusiasts.
  • The Loop / Downtown Chicago – Best area to be central and the Bean is right next to it! 
  • West Loop – If you’re a foodie, you’ll be in heaven in the West Loop.

Luxury Hotels in Chicago

  • The Peninsula Chicago – Located on the Magnificent Mile, this Chicago hotel is a 5-minute walk from the Museum of Contemporary Art. They have a full-service Asian-inspired spa, award-winning restaurants, and spacious luxury guest rooms with city views.
  • The Langham Chicago – Just two blocks away from Michigan Avenue’s Magnificent Mile, this luxury hotel towers above the city in a skyscraper designed by renowned architect Mies van der Rohe. They offer upscale amenities and stylish comfort in the heart of downtown Chicago.
  • The Palmer House Chicago – The Palmer House is a beautiful building and historic hotel that was once Chicago’s liveliest social center. It has hosted a long list of prominent figures—including U.S. presidents, Charles Dickens, and Oscar Wilde. The

Mid-Range Hotels in Chicago

  • The Intercontinental Chicago Magnificent Mile – Located on Michigan Avenue’s Magnificent Mile, this historic luxury hotel is located in the heart of downtown Chicago and features renowned on-site restaurants and an indoor pool with elevated bleacher seating.
  • The LondonHouse Chicago – Sitting on Michigan Avenue and the Chicago River in a historic landmark building, LondonHouse features Chicago’s only tri-level rooftop bar. The hotel is less than 10 minutes’ walk from Millennium Park.
  • Hotel EMC2 Chicago – Located alongside the shopping, dining and entertainment of the famed Magnificent Mile, this boutique hotel is located in downtown Chicago and offers on-site dining and expansive meeting space.

Budget Hotels in Chicago

  • Virgin Hotels Chicago – This downtown Chicago boutique hotel puts a spin on modern luxury and comfort, offering on-site restaurants, a rooftop bar, and nightclub.
  • Millennium Knickerbocker Chicago – Located among the luxury shopping and entertainment on the Magnificent Mile, this 4-star luxury hotel sits within one of the city’s historic landmark buildings and offers unique dining options, a 24-hour fitness center and well-appointed guest rooms.
  • The Whitehall Hotel – A 4-minute walk away from the famous shopping, dining and entertainment on the Magnificent Mile, this boutique hotel offers luxury and historic culture with upscale on-site dining and spacious guest rooms with free WiFi.

When To Visit Chicago

Chicago has four amazing seasons so whenever you choose to visit, there’s something special going on. In my opinion, the best time of year to visit is late summer and autumn. Just be aware that it gets “god doesn’t love you” cold in the winter. You have been warned.

Chicago in Winter From November to January

Christmas is an amazing time to visit Chicago for 3 days. While visiting Chicago for the weekend, check out the Christkindle Market. It’s modeled German Christmas markets so you can sip mulled wine, eat pretzels, shop for Christmas gifts and make merry.

You’ll really get a treat when looking at the Christmas decorations on the Magnificent Mile. Just be aware Chicago’s winters are brutal with the polar vortexes that come down and can reach sub zero temperatures.

Chicago in Spring From March to May

March is very rainy so bring your umbrella. Also, it’s tulip season so you’ll see all the beautiful buds sprouting along the Magnificent Mile. Temperatures around this time are from 4°C to 21°C (40 to 70°F).

March is a great time to visit Chicago during the annual dyeing green of the Chicago River for Saint Patrick’s Day. In addition, you’ll see beautiful cherry blossoms. During late spring in May, you’re going to get the best weather. Just be aware Chicago’s weather is bipolar and it will be hot one day and cold the next.

Chicago in Summer From July To August

Chicago isn’t very humid. The perfect time to visit is during the summer months. Chicago offers up special events like the Taste of Chicago as well as Lollapalooza.

A lot of people go to the beach during warmer months and you’ll see tons of people outdoors. During the day temperatures reach 29°C (84°F) and at night, temperatures are 19°C (67°F).

Chicago in Autumn From September To October 

This is one of my absolute favorite times to be in Chicago as the weather turns mild. There are pumpkin patches out in the suburbs and the city comes alive with autumnal festivities.

I highly recommend checking out Jack’s Pumpkin Pop Up. During the day temperatures are around 18°C (65°F) and at night they drop to 10°C (50°F).

What To Eat in Chicago

I am a bit biased being from the Windy City; however, Chicago has the BEST food scene in the entire US. You have your choices from Chicago’s specialities to delectable delights from around the world. If you’re a foodie, welcome to heaven. Take head of this list of things you have to eat in Chicago.

  • Chicago Style Hot Dog – You can get one of these hot dogs at a Chicago favorite restaurant called Portillo’s. They’ll load your dog the right way with mustard, relish, freshly chopped onions, sliced tomatoes, peppers, and a kosher pickle, nestled in a steamed poppy seed bun.
  • Chicago Style Pizza – This is the most delicious diabetes on a plate you’ll ever bite into and you won’t regret it a bit. These pizzas are loaded with sausage, pepperoni, onions, peppers, mushrooms, and chunky tomato sauce, topped with mozzarella and romano. When visiting Chicago the first time, try Uno Pizzeria & Grill, Gino’s East, Lou Malnati’s, and Giordano’s.
  • Garrett’s Chicago Style Popcorn – The perfect combination of sweet and savory, Chicago style popcorn is hard cheddar and half caramel.
  • Italian Beef Sandwich – Chicago has a huge Italian influence and you won’t get a tastier sandwich elsewhere. As for yours loaded with hot and sweet peppers and dipped in “gravy” (beef juice) for an unbelievably juicy, flavorful meal.
  • Shaved Ice – Otherwise known as Italian ice, you can never go wrong with this cool and icy drink. During warmer weather months, cool off with a shaved ice at Mario’s Italian Lemonade, a mainstay stand since 1954, open May through September.

Chicago Frequently Asked Questions

1. What are the best things to do in Chicago?

Chicago is really well known for its museums. You can spend all day in them and still not have seen the entire thing. Here’s a list of some of my favorite things I’ve always loved to do in the City.

You shouldn’t miss Chicago’s world-class museums, the Willis Tower (Sears Tower), the Chicago River architectural cruise, and deep dish pizza. These are all included in the Chicago City Pass.

2. How many days in Chicago is enough?

Four days in Chicago is plenty of time. If you find yourself with a long weekend, I highly recommend visiting. You can easily fill your Chicago itinerary for one week, but speaking from experience, Chicago gets really pricey.

3. What is the best month to visit Chicago?

The best months to visit Chicago are April through May. The average temperature through April and May during the day is around 10°C to 21°C (50°F to 70°F).

September through beginning of November is also a great time to visit Chicago. The average temperatures between September and October is around 15°C to 21°C (60°F to 70°F). 

Chicago CityPass

The Chicago Explorer Pass is a great way to save money when visiting Chicago. The pass offers you entrance into top attractions such as the Chicago Observation Deck, Field Museum, and Lincoln Park Zoo. You can choose your activities, including a sightseeing cruise or hop-on hop-off bus tour. Book your Chicago CityPass here. 

Chicago Museums You Must Visit

Chicago is full of incredible and must see museums. If that’s your jam, then Chicago honestly has some of the best ones in the country. As a child, I really enjoyed going on field trips to the Field Museum and Adler Planetarium. All museums below are included in the Chicago CityPass. 

The Art Institute of Chicago

The Art Institute of Chicago puts on cool exhibits all year long from the portraits of the Obamas to Monet. They bring in art and artifacts from all over the world and is truly a fantastic place to go if you get the opportunity. 

Adler Planetarium

If you’re a person who constantly finds yourself looking towards the stars, then you’ll get a kick out of the Planetarium. In the exhibit you’ll get shown exhibits like the Chicago night sky and even get a glimpse through the largest aperture telescope in the country.

Chicago Cultural Center

Drawn by its beauty and free public events, hundreds of thousands of visitors come to the Chicago Cultural Center every year, making it the most popular attraction in Chicago.

Field Museum

The Field Museum fuels a journey of discovery across time to enable solutions for a brighter future rich in nature and culture. With almost 40 million specimens and artifacts in our collections—including SUE, the world’s most complete Tyrannosaurus rex. 

Museum of Science and Industry

 Located in Hyde Park, this is one of my favorite world-class museums. It is the largest science center in the Western Hemisphere.

Shedd Aquarium

 Located on the shore of Lake Michigan, Shedd Aquarium brings you eye-to-eye with unbelievable aquatic animals—from Beluga whales to zebra sharks!

Day One Chicago Itinerary

Every three day itinerary for Chicago needs delicious places to eat, scenic places to take photos, and a little bit of Chicagoan culture. Which, I might add, we are mighty proud of.

I also recommend you read The Devil in the White City which is a magical tale of murder, mystery, and magic at the World Fair that placed Chicago onto the world stage and made it a city never to forget.

Beatnik On The River

This incredible restaurant is very beautifully decorated to be a jungle oasis. The food is delicious and a local favorite for bougie brunch or special occasions. Ask for a seat on the patio for views of the Chicago River. Definitely get the babaganoush because it’s to DIE FOR.

Chicago Riverwalk

Since you’ll be at Beatnik on the River, the Riverwalk is walking distance away. It’s a great spot to marvel at the gorgeous architecture of the downtown area. Don’t forget to snap a photo at the Wrigley Building which is one of the most Instagrammable places in Chicago. 

Stroll Down North Michigan Avenue

Next on your walking tour, stroll along North Michigan Avenue. There’s a lot of luxury shops, but also Fannie May candies, and Garret’s Popcorn. The Chicago style popcorn (half caramel and half cheddar) is elite! 

The Chicago Theatre

Just a short walk away is the Chicago Theatre and it is one of the most famous landmarks in the City. Did you know the Frank Sinatra was the first to give a concert here as an honorary Chicagoan?

Plus, he started the tradition of every performing artist coming by and signing the wall. It’s one of those main attractions you definitely don’t want to miss. 

Cloud Gate aka The Bean

 Located in Grant Park, the best time to visit The Bean is super early in the morning. Don’t forget to check out Crown Fountain, Maggie Daley Park (for awesome ice skating in winter) and the Jay Pritzker Pavilion. At the current moment, the Bean is being revamped so there’s a giant wall of construction around it.

Get a Drink and Snacks at Cindy’s Rooftop Bar

This is a super popular place for aerial views of Millennium Park (aka Could Gate aka the Bean). The vibe is great on a Friday night overlooking Lake Michigan. You can make a reservation via Resy here because Saturday nights or any weekend time is poppin. 

Have a Milkshake at Jojo’s Shake Shack

Arguably Chicago’s food scene is the main attraction. At Jojo’s they have seasonal milkshakes. As a basic fall betch, I personally love their autumn menu. The perfect amount of time to spend there is about an hour so you can take pictures on their absolutely adorable patio. 

Willis Tower

Most locals will call the tallest building in Chicago the Sears Tower. The building is a 108-story, 441 meter (1,450-foot) skyscraper. The Ledge at the Skydeck Chicago is the most exciting part because the glass boxes are pretty high above Chicago’s skyline.

If you’re a big film buff, you can stand in the exact area the crew of Ferris Bueller’s Day Off stood for the movie. ProTip: If you use the Chicago CityPass, you get to skip the enormous line to take pictures on The Ledge. 

Day Two in Chicago Itinerary

Three Arts Club Cafe

Three Arts Club Cafe is one of the best restaurants for brunch. Definitely try the avocado salmon toast. The restaurants is spectacularly decorated and wonderful if you love bougie and Instagram worthy locations. Every Chicago itinerary needs a spectacular brunch and ambiance. Click here to get your reservation for Three Arts & Club Cafe.

Navy Pier

While in downtown Chicago, visit one of the most famous amusement parks, Navy Pier. The Centennial Wheel stands at 60 meters (200 feet) and the ferris wheel is a great way to see the city from above. Another favorite Navy Pier location is the Botanical Gardens for proposals. Leave yourself much time to walk around because it’s so easy to get distracted with all the fun to be had! If you’re also a fan of Shakespeare, you can book a show at the Chicago Shakespeare Theater. 

London House Rooftop

The London House Rooftop is a popular place for lunch and drinks. It offers stunning views of the Chicago River and the beautiful city. Go up there for a drink to take photos. Since this is a Hilton Collection Hotel, you’d definitely have an incredible stay here. For rates and booking you can check out the details London House in Chicago here. 

Chicago River Architecture Cruise

I’m totally biased, but the Chicago Skyline is better than the New York skyline. During these architecture tours, your tour guide will give you the historical aspects of all the buildings in the city. They’ll even tell you of the rich history like the Great Chicago Fire and urban legends.

The Architecture River Cruise one of the top Chicago attractions and I 10/10 recommend. I really recommend the sunset architecture boat tour. You can easily book your tickets to the Chicago River Architecture Cruise here. 

The Tilt & Bar 360 At The Hancock

The John Hancock Building is the second tallest building in Chicago. I’ve done a lot of crazy things like walk on the glass floor of Seoul Sky at Lotte Tower and hang my feet off 18 story ledges, but I can’t justify laying on a glass ledge and letting it tilt me forward 100 stories off the ground. You can easily book your tickets for the tilt, a drink, and admission to the Hancock here. 

Day Three in Chicago Itinerary 

Greetings From Chicago Mural

This super touristy mural is also super cute. It has everything on it that is native and special to Chicago. It’s a great place to take photos with your fur baby too.

Across from this mural is Victory Grill restaurant and features all of Chicago’s signature dishes like a gyro, Chicago style hot dog, and an Italian beef sandwich.

Nature Boardwalk at Lincoln Park

Another free location is the Nature Boardwalk at Lincoln Park. This is one of the most popular places in Chicago for special occasion photoshoots. It has amazing views of the Chicago skyline and especially the Hancock.

Eat Chicago Deep Dish Pizza at Pequod’s

Did you really experience Chicago if you didn’t eat deep dish pizza? The big touristy places in Chicago are Gino’s East, Lou Malnati’s, and Giordano’s. If you want a taste of the real Chicago, go local at Pequod’s. Trust me, the wait is worth it. Besides, Chicago Deep Dish is one of the things you must eat in Chicago.

North Avenue Beach Chicago Skyline Photo Spot 

This is another beautiful place for memorable photos of Chicago. You can see the entire breathtaking South Side skyline. These photos are classic, timeless, and a perfect staple to end your Chicago trip. 

Utopian Tailgate

Utopian Tailgate is an eclectic playground bar for adults. You can enjoy a tire swing and even beer pong. I recommend trying the watermelon vodka cocktail. This Chicago rooftop bar is quite popular over the summer so make a reservation. You can book your Resy here. 

Day 4 in Chicago Itinerary

Alas, our four days in Chicago itinerary is coming to an end. Did you know the City is divided into many different vibrant neighborhoods? Each has their own personality and unique local shops. One of the best ways to truly experience Chicago is by getting to know the different neighborhoods. 

Jackson Park 

At Jackson Park, you can see the natural history of Chicago. My favorite part is the Garden of the Phoenix which is a Japanese style garden. You can even swing by the Museum of Science and Industry. It also has close proximity to China Town. Eat yourself the best dumplings at Qing Xiang Yuan Dumplings.

Logan Square

Logan Square is one of the hippest and trendiest neighborhoods in Chicago. Rent has gone crazy high there since the neighborhood cleaned up and became gentrified. Don’t let this stop you! One of the best vegan restaurants, The Chicago Diner is located here. Milwaukee Avenue is also a local favorite for nightlife. The Chicago Comedy Club is also a great place for amateur and up and coming comedians. 

Wrigley Field

I’m not a Cubs fan, but I’m definitely a Wrigley Field fan. Haven’t you heard? Chicago is a drinking town with a sports problem. The bars on the Northside in Uptown and Wrigleyville are especially great! Book your tickets to a Cubs game in Chicago here. I recommend going to Rizzo’s after a game. 

Optional Day Trip: Indiana Dunes National Park

Alas… I spent many a drunk summers at the Dunes. It was THE place to take a day trip outside of Chicago. The great thing about it is it was more fun because we didn’t get caught.

All you have to do is grab some friends, take food for a picnic, and you have a recipe for meeting other young people, enjoying a summer day, and making new friends. 

I hope you found everything you were looking for in this 4-day Chicago itinerary. You will definitely fall in love with the Windy City and want to visit again and again. Besides, Chicago is a much better place to visit than NYC. 😉 

This post contains affiliate links which means at no additional cost to you, I make a small commission to help keep Gina Bear’s Blog running. Thanks for your support!

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