The Ultimate Guide to Visiting Chicago: All You Need to Know

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Looking for an insider’s guide to visiting Chicago? I have lived in Chicago for over 30 years, it never gets old and I love helping visitors see Chicago for the beautiful city that it is.

Find everything you need to know about visiting Chicago right here! Our ultimate guide covers the best attractions, restaurants, entertainment, and more.  

Plus, get helpful tips on where to stay and how to get around the city (we cut right to the chase). Don’t miss out on all realness that we have to share!

Overview of Chicago

chicago theater marquee

Chicago was discovered in the late 1600s by French explorers led by René-Robert Cavelier, Sieur de La Salle, who traveled down the Illinois and Mississippi Rivers.

They encountered the native Miami and Illinois tribes, who had long inhabited the region. The name “Chicago” comes from the native word “shikaakwa,” which means “wild onion” or “skunk.”

In the early 1800s, Chicago was still a small trading post. It is because of the Chicago River that the city became a major transportation hub. Its location and transportation advantages would eventually lead to its growth as a major city and commercial center.

Chicago is an ideal destination for tourists. From its deep-dish pizza to its world-class museums to its iconic architecture to hip neighborhoods, there are plenty of reasons why you should visit Chicago.

So, whether you’re looking for a relaxing weekend getaway or an action-packed adventure, this ultimate guide will help you plan your trip and make the most of your time while visiting Chicago.

Chicago has seen it all. From the Great Fire of 1871 to the World’s Columbian Exposition in 1893, from Prohibition to modern-day skyscrapers, Chicago has been at the forefront of history for centuries.

In this guide, we’ll explore some of the city’s top attractions and things to do. We’ll also uncover some of the best places to eat and drink in town. So if you’re ready to experience all that Chicago has to offer, let’s go!

Getting to Chicago

woman on train

Airport Arrivals

Welcome to Chicago! Flight touchdowns are always a relief and it’s exciting to be on your way to experience the Windy City after a long journey!

When you first land at Chicago O’Hare International Airport (airport code ORD) or Chicago Midway International Aiport (airport code MDW), you’ll clear immigration and customs if need, then stop at the baggage carousels on the lower level and pick up your luggage if you checked any in. 

Ride Sharing

Ride-sharing services are on the same level as baggage claims for both airports. If you have arranged for pick up (eg. taxi, Lyft, Uber), make sure you note the door you are exiting because the service may ask you to meet at a specific exit.

Transfer Services

Transfer services are available at either airport, but you must make reservations in advance. It’s easy to get to downtown Chicago from the airport, but with many people arriving simultaneously, it can be a pretty busy line for taxis and traffic can be terrible at peak periods or with inclement weather.

You can pre-book a transfer service to make your journey more comfortable after a long flight. You can also order a taxi of any size, including a bus for groups. We highly recommend American Taxi. When you book online, you only need to specify the pickup date, a time and choose a payment method. Once booked, you’ll receive a voucher by email.

Drivers will have nameplates with your details when they pick you up at the airport. After you collect your luggage, you will take a brief walk to the car, and your driver will bring you to your hotel. Book a transfer service to enjoy a comfortable and hassle-free journey while visiting Chicago.

Rental Cars

Unless you plan to explore the outer parts of the city, you won’t need a car. By eliminating rental and parking fees, you can realize some savings while visiting Chicago.

But if you do need a car, it’s easy to rent one at the airport. The O’Hare airport transport (rail) that take you to the car rental provider and there are several agencies to choose from including Avis, Hertz, Budget, Enterprise, National, Dollar, and Alamo.

O’Hare has a wider selection of budget-friendly companies like Sixt, Payless, Fox, and Thrifty. We’ve found that Budget and Dollar have more competitive rates. You will need to present your reservation, driver’s license, and proof of insurance. The rail is accessed from the upper level across the sky bridge. The car rentals are at the very last stop past the long-term parking lots.

Check to confirm that a rental car can be covered under your car insurance, otherwise, you’ll need to purchase it from the rental agency to protect yourself from financial burdens in the case of an accident. 

Trains to Chicago

You can take the CTA train which is a public transportation service. At O’Hare airport, you’ll need to follow the signs marked “City Trains” and catch the Blue line. The entrance to the CTA train is at Terminal 2 on the lower level. To get there from other terminals, you’ll need to take the airport transport (rail). Access to the rail is on the upper level.

At Midway airport, follow the signs to the trains and catch the Orange line. Kiosks to purchase fares are located at the train station entrance.

Take advantage of the Ventra Card, it is re-loadable card that you can use to enter the train station while saving money with each use.

In addition, you would only need one card for your group if you are traveling together, just swipe once for each passenger.  This makes it super easy to use public transportation while visiting Chicago.

Driving to Chicago + Tolls

When visiting Chicago by car, you will learn that three expressways intersect with the city and depending on your destination outside of the city limits, you may be required to pay a toll.

  • I-290 is an interstate highway that runs east to the Chicago Loop
  • I-55 is a highway that runs in a northeastern direction to Chicago
  • I-90 is an interstate highway that runs east and west to and from Chicago

Illinois has eliminated cash tolling. So the options for paying tolls are to use the Pay-by-Plate, E-ZPass, or I-Pass. The Pay-by-Plate online platform allows you to pay tolls without a transponder and it is a great option for rental cars.

You will need to go to the Illinois website, identify the car you were driving by the license plate, then pay the tolls due.

I-PASS is a program that requires a transponder to be mounted on the inside of your car. When you pass through the toll area, the tolls are paid electronically from the balance on your I-PASS account. The transponder can also be used with rental cars, or you can elect to use a transponder that the rental agency provides.

If you already have a transponder, it may be used within Illinois if it is part of the E-ZPass group that is comprised of 19 states (Massachusetts, Minneapolis, Illinois, Indiana, Ohio, Pennsylvania, New York, New Hampshire, New Jersey, Rhode Island, Maine, Maryland, Virginia, West Virginia, Kentucky, North Carolina, Delaware, Georgia, and Florida).

Once you have reached the city, you can find available parking garages using Spothero.com or a hotel garage.

Use our guide to discover how easy it is to get around Chicago on foot and by using public transportation (this is a must read!). There is an explanation of the various options for public transportation and their costs in this resource. We also share some tips for driving in Chicago.

Lastly, make sure you have a local SIM Card to use your cell phone in the United States if you are traveling from out of the country.

Most Popular Neighborhoods in Chicago

guide to visiting chicago
Credit: Choose Chicago

There are plenty of reasons to visit other neighborhoods when you’re visiting Chicago. They’re usually historic and full of character, and they have a lot of great restaurants, nightlife, and community activities.

Another great neighborhood for family activities is Chinatown. It’s one of the best places to enjoy Dim Sum in Chicago.

Plus, you’ll be able to people-watch and maybe even spot a celebrity or two. So, when planning an itinerary for Chicago, consider these neighborhoods when looking for accommodations because they are closest to top attractions and points of interest.

Lincoln Park

Recommendations: Hotel Lincoln | Majestic Hotel | Claridge House | The Neighborhood Hotel | Suite Home Chicago

West Loop (Fulton Market)

Hotel Recommendations: Nobu Hotel | The Hoxton Hotel | The Emily Hotel | SoHo House Chicago | Homewood Suites by Hilton

Chicago Loop

Hotel Recommendations: The Chicago Athletic Association | Palmer House by Hilton | Hotel Julian | Renaissance Chicago

River North

Hotel Recommendations: Royal Sonesta | Embassy Suites | Freehand Chicago | Fairfield Inn & Suites | SpringHill Suites

Wrigleyville

Hotel Recommendations: City Suites | Hotel Versey Days Inn | Best Western Plus | The Chicago Hotel

Magnificent Mile

Hotel Recommendations: InterContinental Hotel | Courtyard by Marriott | Park Hyatt | The Drake | The Peninsula

Streeterville

Hotel Recommendations: Loews Hotel | Hyatt-Centric Chicago | Ivy Hotel | Sheraton Grand Hotel | DoubleTree by Hilton

Accommodations in Chicago

aerial view of skyline
View from Chicago Centennial Wheel

From luxurious hotels to affordable hostels to cozy bed and breakfasts to high-rise apartment rentals, this city has every type of accommodation for every type of traveler. However, there are several factors you should consider when selecting a hotel when visiting Chicago.  

Location: Consider the proximity of the accommodation to your destination and the surrounding area. Is it close to public transportation, attractions, restaurants, and other amenities you may need during your stay?

Price: Determine your budget and find an accommodation that fits within it. Keep in mind that cheaper options may have fewer amenities or be located further from the center Chicago activities. When visiting Chicago, there will always be a trade off between location and price.

Check rates for Accommodations in Chicago

Amenities: Make a list of amenities that are important to you, such as Wi-Fi, parking, air-conditioning, laundry facilities, and breakfast. Check if the accommodation provides these amenities or if they come at an additional cost.

Room size and type: Consider the size and type of room you need. Do you prefer a single or double bed, a suite or a standard room, a balcony or a lake view? Ensure that the accommodation offers the type of room that suits your preferences and needs.

Reviews: Read reviews from previous guests to get an idea of the accommodation’s quality, service, and cleanliness. Look for reviews on reputable websites, such as TripAdvisor or Booking.com.

Safety: When renting an apartment or home while visiting Chicago, inquire about the security standards of the accommodation, such as security cameras, locks, and fire exits. You may also want to check the safety of the surrounding area.

Accessibility: If you have specific mobility needs, check if the accommodation offers accessible features, such as wheelchair ramps, elevators, and handicap-accessible rooms.

Top Chicago Museums to See

Lion at the art institute of chicago
Art Institute of Chicago

Museums are important because they preserve history and enable you to learn about other cultures.

They are also a great way to spend a day when visiting Chicago, especially for rainy day activities. Visiting Chicago because museums can be educational, entertaining, and even inspirational.

Best Museums in Chicago

Boasting one of the planet’s premier collections of Impressionist, Modern and Contemporary art, the acclaimed Art Institute of Chicago counts among the world’s most esteemed museums. Alongside the best things to see at the Art Institute of Chicago, visitors can also behold the Institute’s famed holdings of iconic American works.

  • The Museum of Science and Industry | 5700 S Dusable Lake Shore Drive
  • The Shedd Aquarium | 1200 S Dusable Lake Shore Drive
  • Adler Planetarium | 1300 S Dusable Lake Shore Drive
  • The Chicago Children’s Museum | 700 E Grand Ave
  • American Writer’s Museum | 180 North Michigan Ave

Best Art Museums in Chicago

  • The Art Institute of Chicago | 111 S Michigan Ave
  • Driehaus Museum | 40 East Erie St
  • Museum of Contemporary Art Chicago | 220 E. Chicago Ave
  • National Museum of Mexican Art | 1852 W. 19th St.
  • Loyola University Museum of Art | 820 N. Michigan
  • Small Museum of Art | 5550 S. Greenwood Ave
  • National Museum of Puerto Rican Arts & Culture | 3015 W. Division St.
  • Pullman Porter Museum | 10406 S. Maryland Ave.

Best History Museums in Chicago

  • DuSable Black History Museum and Education Center | 740 E 56th Pl
  • The Field Museum of Natural History | 1400 S Dusable Lake Shore Drive
  • Medieval Torture Museum | 177 N State St
  • Chicago History Museum | 1601 N. Clark St
  • National Hellenic Museum | 333 S. Halsted St
  • Chicago Sports Museum | 835 N. Michigan Ave
  • Jane Addams Hull-House Museum | 800 S. Halsted St
  • Pritzker Military Museum & Library | 104 S. Michigan Ave
  • Ukranian National Museum | 2249 W Superior St.
  • Clarke House Musuem | 1827 S Indiana
  • Swedish American Museum | 5211 N. Clark St

Most Popular Outdoor Activities

guide to visiting chicago
Credit: Graham Chapman

Millennium Park 

This is Chicago’s award-winning public park located in the heart of downtown. You will love the expansive acreage of green space and gardens for taking a stroll. Spending time outdoors in the large green spaces are a great way to relax and unwind when visiting Chicago.

From art installations, summer concerts, and interactive programs to ice skating, biking, and running trails, Millennium Park has something for every season of the year.

If you’re looking for a fun day out with friends or family or just want to relax in the sun, add Millennium Park to your itinerary.

Navy Pier 

How about 3,300 feet of pure fun on the lake? Navy Pier is a very popular for visitors and locals. The pier has multiple levels and sections that will pique your interest both indoors and outdoors.

From boat rides and sightseeing tours to shopping, dining, entertainment, theater, amusement rides, or just people-watching, there are lots of ways to experience the pier when visiting Chicago.

You can also rent bikes for a lakefront ride, take an evening dinner cruise out with friends, or for a romantic evening. 

Chicago Riverwalk

The Riverwalk is a beautiful public space located along the banks of the Chicago River.

It is a popular destination for locals and visitors because there are a variety of activities and attractions to explore.

You can rent electric boats, go kayaking, see art exhibits, and enjoy outdoor dining with live music.  

The Riverwalk has a nice view of Lake Michigan on the east end, adirondack chairs to relax on the west end, and lots of bars and restaurants in between.

The Lakefront Trail

This is a scenic 18-mile path that runs along the shoreline of Lake Michigan. It’s the perfect place to get away from the hustle and bustle of city life and take in some fresh air when visiting Chicago.

You can explore nature at its finest with stunning views of the lake, take in some culture at one of the Chicago museums and attractions, or simply relax with a picnic on one of its many beaches.

Outdoor lovers can also enjoy a few hiking trails near Chicago.  The 606, or Bloomingdale Trail, is also great for walking, jogging, and biking. 

Chicago Sports Stadiums

Chicago has a die-hard sports scene with passionate fans. Along with professional teams in baseball, football, basketball, and hockey, the city also hosts minor league and college sports events.

Fans of these teams can be found cheering them on throughout Chicagoland during their respective seasons.

Wrigley Field

📍1060 W. Addison St.

  • Chicago Cubs – Major League Baseball

United Center

📍1901 W Madison St

  • Chicago Bulls – National Basketball Association
  • Chicago Blackhawks – National Hockey League

Soldier Field

📍1410 Special Olympics Dr

  • Chicago Bears – National Football League
  • Chicago Fire FC – Major League Soccer

Guaranteed Rate Field

📍333 W 35th St

  • Chicago White Sox – Major League Baseball

Wintrust Arena

📍200 E Cermak Rd

  • Chicago Sky – Women’s National Basketball Association

The city also boasts two Major League Soccer clubs: the Fire and Red Stars. It’s also easy to catch games at a university if you are visiting alumni.

There are also plenty of amateur and recreational sports leagues for those who enjoy playing themselves.

Attending a sports game is a great way to experience Chicago’s sports culture, soak up the atmosphere and cheer for your favorite team when visiting Chicago.

We have great information to help you plan a Cubs weekend at Wrigley Field!

Theater & Comedy

entrance to auditorium theater in chicago
Auditorium Theatre

There’s something about seeing a live performance that just can’t be beaten.

I’ve been to a few different theaters in the city, but my favorite has to be the Chicago Theater. There’s just something about this historic spot with the iconic marquis.  

The theater district is bustling with arts and performances, and you’ll be able to see a variety of shows during your stay.

From Broadway musicals to local productions, you’ll find that the small theater performances are surprisingly well-done.

Theatre Venues

  • Goodman Theatre | 170 N. Dearborn St
  • Auditorium Theatre | 50 East Ida B. Wells Drive
  • Lookingglass Theatre Company | 821 Michigan Ave
  • Victory Gardens Biograph Theater | 2433 N Lincoln Ave
  • Theater on the Lake | 2401 N Lake Shore Dr
  • Steppenwolf Theatre | 1650 N Halsted St
  • Victory Gardens | 2433 N Lincoln Ave

Broadway in Chicago

  • Nederlander Theater | 24 W. Randolph
  • Cadillac Theatre | 151 W. Randolph
  • CIBC Theater | 18 W. Monroe

Comedy Clubs

  • Zanies | 1548 N Wells St
  • The Second City | 230 W. North Ave
  • The Laugh Factory | 3175 N. Broadway

You will be particularly impressed with the level of talent on display too. The acting, singing, improv, and dancing are all top-notch, and you’ll every minute of the experience. 

If you are short on time while visiting Chicago, I highly recommend The Second City just for the experience of being at an iconic comedy club that has launched the careers of many comedians who appeared on Saturday Night Live.

Every February, Chicago hosts Theater Week where you can attend performances at a reasonable value. If you’re looking for an exciting theater scene, definitely check out Chicago’s theater district. You won’t be disappointed!

Shopping in Chicago

boat on chicago river near Magnificent Mile
View of Michigan Ave from Wacker Dr

There is no shortage of places to shop while visiting Chicago! You can find great retail therapy in the various neighborhoods and do some serious shopping in Chicago, and let me tell you, it will be a blast!

Start on Michigan Avenue, where all the high-end stores are located. It is so much fun trying on clothes and picking out new outfits.

Next, head over to State Street, where there are tons of great shops and boutiques. You’ll spend hours browsing and will find some amazing deals on clothes and jewelry.

You can even grab a few souvenirs for friends and family back home.

  • Magnificent Mile  | Between Chicago River and Oak Street
  • State Street | Between Adams and Lake Street
  • Block 37 | 108 N. State St.
  • The Shops at North Bridge | 520 N. Michigan Ave.
  • The Water Tower Place | 835 Michigan Ave.
  • 900 North Michigan Shops | 900 North Michigan Ave.
  • Fashion Outlets of Chicago | 5220 Fashion Outlets Way, Rosemont

There’s nothing like a shopping spree in the Windy City!

Whether you’re looking for designer duds on Michigan Avenue or bargains on State Street, Chicago is a shopper’s paradise. And with all the great restaurants and attractions nearby, it’s easy to make a day of it.

Indoor and Outdoor Chicago Markets

  • Chicago French Market | 131 N Clinton St | Monday–Friday from 7AM to 7PM, Saturday 9AM-4PM
  • Randolph Street Market | 1341 W Randolph St | Saturday–Sunday from 10AM to 5PM
  • Maxwell Street Market | 800 S Desplaines St | Friday from 9AM to 4PM, Sunday from 7AM to 2PM

Dining in Chicago

couples sitting at tables on riverfront
Chicago Riverwalk

The food scene in Chicago is nothing short of epic.

If you’re looking for an amazing dining experience while visiting Chicago, you’ll want to check out some of the city’s top restaurants including the Michelin-starred Alinea.

If you love pizza, then you’ll want to check out some of the best places to enjoy pizza in Chicago.

From deep dish to thin crust, you will find it is a unique Windy City experience! We’ve listed the best spots for deep-dish or thin-crust pizza in Chicago. 

Whether you’re looking for great Chicago breakfast spots, romantic dinner for two or a night out with friends, or plant-based restaurants, these spots are so chill and tasty. So, without further ado, here are our picks for the best places to eat in Chicago!

Fine Dining

  • Alinea | 1723 N. Halsted St
  • Mastro’s | 520 N. Dearborn St
  • The Signature Room | 875 North Michigan Ave

Casual Dining

  • Time Out Market | 916 W Fulton Market
  • The Purple Pig | 444 Michigan Ave
  • Grand Lux Cafe | 600 N Michigan Ave

Romantic Restaurants

  • Gejas | 340 W Armitage Ave
  • Gibsons Italia | 233 N Canal St

Chicago Pizza

  • Lou Malnati’s | 439 N Wells St (various locations)
  • Giordano’s | 730 N Rush St (various locations)
  • Pizano’s | 61 E. Madison (various locations)
  • Pequods | 2207 N Clybourn Ave
  • Gino’s East | 162 E Superior St
  • Pizzeria Uno | 29 E Ohio St

Must See Annual Chicago Events & Festivals

people viewing a irish band in a parade
St. Patrick’s Day Parade

What I love most about Chicago is that it provides opportunities for people to come together from different communities and celebrate during any season of the year.

The holiday celebrations in Chicago are magical and Christmas shopping in Daley Plaza while eating German food at Christkindlmarket is a crowd favorite. 

This is a list of recommended don’t miss festivals when you are visiting Chicago. When visiting Chicago for major events, be sure to book accommodations well in advance.

February

  • Chicago Auto Show
  • First Bites / Chicago Restaurant Week

March

  • St. Patrick’s Celebrations & Dying the Chicago River

June

  • Chicago Blues Festival
  • Chicago Food Truck Festival
  • Chicago SummerDance (thru September)

July

  • The Taste of Chicago
  • Pitchfork Music Festival
  • Windy City Smokeout

August

  • Lollapalooza
  • Chicago Air & Water Show
  • Bud Billiken Parade
  • Ribfest Chicago
  • Taste of Greektown

September

  • RiotFest
  • Chicago Jazz Fest
  • Lakeview Taco Fest
  • Apple Fest
  • Pilsen Mexican Independence Day Parade

October

  • Chicago Marathon

November

  • Chicago Christkindlmarket (thru December)
  • Magnificent Lights Festival

Day Trips & Excursions from Chicago

Rt 66 sign Chicago Road Trip
Credit: Wikimedia Commons

Feeling adventurous? Or perhaps you’re visiting Chicago again and you want to wander beyond the Bean?

If you love to pack in as much as possible, then a day trip from Chicago may be just what you need. We have a list of places that will take two hours to five hours by car.  

Milwaukee, Wisconsin

Union Pier, Michigan

Frankenmuth, Michigan

Holland, Michigan

Indiana Dunes State Park – Northwest Indiana

Galena, Illinois

Oak Park, Illinois

Starved Rock State Park – Oglesby, IL

Lake Geneva, Wisconsin

Garfield Park Conservatory, Chicago

Door County, Wisconsin

Michigan City, Indiana

Planning Your Visit to Chicago

view of lake michigan
View of Lake Michigan from Centennial Wheel

The Best Time to Visit Chicago

Seriously, there is no wrong time for visiting Chicago because there are always iconic sights, colorful local culture, and must-sees to create an itinerary that will make your stay exactly what you need.  

If you are short on time, we highly recommend the Big Bus Tour Chicago because you’ll be able to visit 80% of what Chicago is best known for in about two hours.

For the best weather conditions, we recommend visiting Chicago between April and June. If you are comfortable traveling in 90-degree temperatures, July and August are good months to visit Chicago, but you may want to add some lakeside activities to stay cool.

September through November are also good months for visiting Chicago. It borders the cooler season in Fall, but for the most part, you will avoid snowy weather.

December through February are the coldest months. Temperatures begin to warm in March with occasional snow and rain.

Knowing how to dress in Chicago can be tricky in transitional season.

How Long Should You Visit Chicago

To see the top attractions while visiting Chicago, you should allow at least three days for your visit.

Most top Chicago attractions and architecture tours are anywhere from 5 to 25 minutes apart and by the time you factor in lunch and the sights, you can comfortably squeeze in two to four activities per day.  

Of course, there are some factors that you’ll need to consider when deciding how many days to stay in Chicago such as where you want to go, what you want to do and the pace at which you want to spend your days.   

What to Pack for Each Season

When visiting Chicago in Spring and Autumn, clothing should be layered so that you can adjust for warmth throughout the day. Your base layer should be slightly fitted like a basic tee or long-sleeved top. The mid-layer should be thicker but non-restrictive — a hoodie or light sweater will work, just make sure it is breathable. Finally, the outer layer should be a heavier piece that complements your first two layers and brings the outfit together, like a pea coat or rain jacket. 

When visiting Chicago in Summer, wear breathable clothing like cotton. Linen is also a good choice for staying cool, but it’s not one of the best wrinkle-free materials for travel. It’s easy to maximize outfits in summer by doubling up on the wear. Cargo pants and summer dresses are also great options for mixing and matching styles. 

When visiting Chicago during the colder season, you need to be winter ready. A coat, scarf, insulated gloves, and boots are essential for snowy and wet weather. Dress for warmth, because the “hawk” is real! If you arrive in Chicago from a warmer climate and don’t want to invest a lot of money, you can try thrifting at a Chicago store. 

Final Thoughts on Visiting Chicago

Chicago is one of the most vibrant cities in the United States. With its rich history and modern attractions, it’s no wonder why millions of people look forward to visiting Chicago each year.

Come for the iconic architecture and world-class museums, but stay for the community vibes, the food, and the culture.

Whether you’re visiting Chicago for a weekend getaway or an extended vacation, this ultimate guide will help you plan your trip and make sure you don’t miss out on anything!

During your visit, you can learn about the history of Chicago, discover why it’s such a great destination, and use these tips on how to make the most of your stay.

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Have a question about Chicago? Feel free to email me!


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