The Travel Guide to Chicago


Good to Know

When to go:

Average Costs


Welcome to Chicago

Welcome to Chicago, a city of world-class restaurants and museums, theater, architecture, shopping, parks, a lake so big it can trick you into thinking you’re on the ocean, and more. From taking in history on a river tour to sipping innovative cocktails, biking along the lake or shopping your way down Michigan Ave, there truly is something for everyone. 

Most importantly, Chicagoans love Chicago, and it’s always fun to visit a city where the residents are enthusiastic about showing it off. Need extra recommendations? Just ask. This is the Midwest after all.

Before you go, learn more about the history and culture of Chicago.

Who’ll Love Chicago

Couples who like city getaways; foodies seeking a mix of innovative global cuisine and seasonal Midwestern fare; families who love museums; just about anyone and everyone

How to Budget for a Trip to Chicago

Chicago has something for every budget, from inexpensive food stands to Michelin-star restaurants, hostels to high-end hotels. The average hotel price is around $150, but there are hostels closer to $25 and luxury hotels upwards of $400. Likewise, you could easily spend $100+ on a fancy dinner, but you can also grab a Chicago-style hot dog or some fantastic Mexican, Indian, Turkish, or Vietnamese food for around $10.  

Safety Considerations

Like any major city, Chicago is mostly safe, but has some risks. Don’t leave your bag unattended on the metro or in a busy coffee shop, for example. Women should be careful walking late at night, like in most cities. Chicago has notoriously dangerous neighborhoods, mainly on the south and west sides. Gun violence in these neighborhoods is mostly targeted and highly unlikely to affect tourists. 

Weather in Chicago

Chicago is hot in the summer, frigid in the winter. Average temperatures from December to February are in the high 20s and low 30s, bumping up by about 10 degrees each month until July and August, where they hover in the 80s before crawling back down. It can be humid in the summer, and winds in the winter can often make it feel much colder than it actually is. It is typically cooler near Lake Michigan, on the east side of the city. 

Chicago average temperature chart.

When to Visit Chicago

Chicago really comes alive in the summer, when residents take advantage of the weather and numerous outdoor activities, patios and parks. To avoid the hottest days, come in May, June, or early September but if you plan to hit the beach and don’t mind a little humidity, July and August can be fantastic as well. Fall (late September to early November) is also a beautiful time to visit. 

December through March typically see the fewest crowds and lowest prices, but you’ll have to contend with some very cold days that can make sightseeing unpleasant. 

Money Saving Tips 

See the city by foot or bike: Chicago is a fantastic walking city. Though it’s large, walking from neighborhood to neighborhood gives you a feel for the city and the little things that make each area unique. You can also walk or bike the entire north-south length of the city on the Lakefront Trail, which has exit points every few blocks to get back into the city. 

Embrace free tourism sites: Some of Chicago’s most iconic attractions are also free. Millennium Park, home of Cloud Gate (better known as “the Bean”) is always free to visit and in summer months also has free concerts, movies and workout classes. A walk along the Chicago Riverwalk provides the city’s best views of beautiful, historic buildings like the Tribune Tower and Wrigley Building. You’ll also pass art installations, civic memorials and a floating garden. Around the city, keep an eye out for public art like Picasso’s “The Picasso,” Calder’s “The Flamingo,” Chagall’s “The Four Seasons,” and dozens of murals from local artists. 

Visit museums for free or bundled rates. Chicago’s museums host free days multiple times a year. See if one of the dates times up with your trip. If not, and if you plan on visiting multiple museums and attractions during your stay, the CityPass offers a bundled rate. 

What to See, Do, and Eat in Chicago 

The Top 10 Things to Do in Chicago

the bean in Millennium Park.
  1. Architecture River Tour: The Chicago Architecture Center’s river tour is led by docents who can tell you all about the history, design and engineering feats of the buildings along the river, from the world’s first skyscraper to the city’s new tallest building. 
  2. Navy Pier: Navy Pier is touristy, but fun, especially for families. The Chicago Children’s Museum is here, as well as the Centennial Wheel and river/lake cruises. There’s a fireworks display every Wednesday and Saturday throughout the summer, and the new Offshore rooftop restaurant is the perfect place to take them in.  
  3. Wrigley Field: You don’t need to be a baseball fan to appreciate the history of Wrigley Field, home of the Chicago Cubs and unique for its location right in the heart of a neighborhood. 
  4. Lincoln Park: Stroll through the city’s largest park, where you can visit the Lincoln Park Zoo, the botanical gardens (both are free), walk along a conservation boardwalk, take in historic statues, visit the farmer’s market on Saturdays in the summer, picnic, and much more. 
  5. Lake Shore Drive: The 18.5-mile bike and walking path is a beautiful way to see why Chicago is often called the “third coast.” The skyline meets Lake Michigan around Oak Street Beach. 
  6. Millennium and Grant Park: No visit to Chicago is complete without a photo in the mirrored Bean. In neighboring Grant Park, check out the historic Buckingham Fountain near where Barack Obama gave his victory speech and the Cubs celebrated their World Series win in 2016. 
  7. The Art Institute of Chicago: One of the country’s premiere art museums, the Art Institute houses works such as American Gothic, Nighthawks, Monet’s Stacks of Wheat and early Andy Warhol pieces. 
  8. Museum Campus: In one strip, you can visit the Shedd Aquarium, a massive aquarium holding more than 32,000 animals in a building originally built for the World’s Columbian Exposition; the Field Museum, a natural history museum with full dinosaur skeletons and much more, also in a historic building; and the Adler Planetarium, a museum of space and physics with an amazing 360-degree theater. 
  9. Museum of Science and Industry. In Jackson Park near the University of Chicago campus, this museum features ​​a full-size replica coal mine, a German submarine U-505 captured during World War II, the command module of Apollo 8 and much more. 
  10. Catch views from the top: Willis Tower, once the world’s tallest building, and the John Hancock building both have skydeck experiences. At Willis Tower you can walk out on a ledge 103 stories up and see the city from every direction, while at the John Hancock building you can step out into an angled box 1000 feet above the city. 

The Local Picks for Top Attractions and Activities in Chicago

beach in Chicago.
  1. Swim at city beaches. Chicagoans flock to the beaches in summer months. At Oak Street Beach, where you can dive into Lake Michigan just steps from Michigan Avenue, you get a true city/beach experience. Nearby, North Avenue beach is packed with volleyball courts and beach parties, plus there’s a large restaurant and bar. Farther north, Montrose Beach is more relaxed and great for families or those hoping to simply relax on the sand. 
  2. Picnic in Humboldt Park. Another large Chicago park, Humboldt Park has a few walking trails and a small lake. There are almost always food carts selling hot dogs, paletas and more. 
  3. Visit a comedy club. Second City is Chicago’s most famous improv show, but there are dozens of stand up and improv clubs across the city. 
  4. Eat in Logan Square. Tourists typically dine downtown or in the West Loop, but Logan Square is one of Chicago’s best food neighborhoods. You can’t go wrong with most restaurants in the area, but Lula Cafe, Osteria Langhe, and Longman & Eagle stand out. 
  5. Walk the 606. The western equivalent of the Lake Shore Trail, the 606 is an elevated trail on a former railroad track, with public art and green spaces along the way. 
  6. Embrace street festivals. Almost every one of Chicago’s 77 neighborhoods throws a festival at some point between spring and fall. Wicker Park Fest, Old Town Art Festival, Edgewater Arts Festival, and on and on. Check if there’s a festival during your travel dates and embrace neighborhood city life. 

What to Eat & Drink in Chicago

deep dish pizza

In Chicago, chefs are celebrated and new restaurants open every week, meaning there’s a never-ending supply of fantastic food–but without the pretentious vibe that sometimes takes hold of great food cities. This is the Midwest after all. From hot dogs and tacos to Michelin-starred experiences, and everything in between, Chicago really has it all. 

  • Deep dish. Chicagoans will argue over deep dish, but many agree Lou Malnati’s is the best. It has a flaky, buttery crust and is topped with Wisconsin mozzarella, a special sausage blend (if you order the classic), a chunky, sweet plum tomato sauce on top of the cheese and toppings, and a sprinkle of additional cheese and seasonings. 
  • Chicago dogs: Make sure to eat a Chicago-style hot dog: an all-beef frank topped with yellow mustard, pickle relish, chopped onions, tomato, a pickle, peppers, and a sprinkle of celery salt in a poppy seed bun. No ketchup allowed. Try Jimmy’s Red Hots, The Wiener’s Circle (where be warned, it’s tradition to insult customers), Superdawg Drive In, or Portillo’s
  • Lula Cafe: A love letter to the Midwest, Lula Cafe is one of Chicago’s earliest and still best farm-to-table spots. 
  • Alinea: Chef Grant Achatz’s playful, Michelin-starred spot often ranks highly on the “best restaurants in the world’ list.”
  • Carnitas Don Pedro: Chicago has some of the best Mexican food in the country, including slow-cooked carnitas with all the fixings at Carnitas Don Pedro in the Pilsen neighborhood. 
  • Pat’s Pizza: Chicago isn’t only deep dish. Thin and crispy tavern-style is possibly even more popular, and Pat’s Pizza makes one of the best. 
  • Jibaritos y Mas: The jibarito, a sandwich made with grilled plantains instead of bread, aioli, meat, cheese, lettuce and tomato was invented in the Humboldt Park neighborhood of Chicago. Get your fix at Jibaritos y Mas
  • Porto: Porto is one of the most beautiful restaurants in Chicago, and also one of the best places for fresh seafood. You’ll feel like you’re on the coast of Portugal, even in the dead of winter. 
  • Monteverde: Watch chefs roll out handmade pasta before your eyes and feast on simple and delicious Italian cuisine from Chef Sarah Grueneberg. 
  • Mako: Chef BK Park serves exquisite omakase in an unpretentious setting. 
  • Virtue: The American South meets Chicago at this warm and welcoming Hyde Park spot from Chef Erick Williams. 

Where to Stay in Chicago

There are hundreds of hotels in Chicago, mostly concentrated in the Loop, River North and West Loop, though there are options in almost every neighborhood. Prices vary by season, but generally range from about $110 to $300. There are several popular hostels as well, with prices from about $25 to $100. Airbnb is a great option. There are homes listed in every neighborhood and in a wide range of styles and prices. 

Top Chicago Neighborhoods for Visitors

Lincoln Park in Chicago.

Lincoln Park: Lincoln Park is home to beautiful homes and lots of boutiques and restaurants, as well as the sprawling park.

Gold Coast: The swankiest neighborhood in Chicago, here you’ll find bars and restaurants where the point is to see and be seen. You’ll also find gorgeous historic mansions, especially on State St. and Dearborn St. 

Wicker Park: An eclectic neighborhood with art galleries, vintage stores and cool fashion boutiques, bookstores and cafes, and lots of great food. 

Lakeview: Lakeview encompasses a few smaller neighborhoods, like Wrigleyville, where you can catch a Cubs game, and Boystown, the city’s LGBTQ+ enclave. 

Recommended Hotels in Chicago

  • Freehand (~$35 per night): Trendy hostel in the heart of the city 
  • LondonHouse Chicago (~$200 per night): A posh spot in a historic building, with a rooftop bar showcasing some of the best views in the city
  • Chicago Athletic Association (~$175 per night): A stylish hotel near Millennium Park with a game room, speakeasy, and multiple dining options 
  • Hotel Lincoln (~$150 per night): A neighborhood vibe with park views

Getting Around in Chicago

Public Transportation Options in Chicago

Though geographically large, Chicago is easy to get around. Public transport is simple and affordable–the “L” train, or metro, is $2.50 per ride and the bus is $2.25. You can get pretty much anywhere in the city by bus or metro. 

Uber and Lyft are another easy option. Taxis are less prevalent, but can be flagged downtown. Taxis and rideshare apps have similar prices. If you drive, pay attention to parking signs. In neighborhoods, parking is often free but there are restrictions on who can park where. Downtown, parking lot rates range from $20-$100 depending on the lot and time. 

Chicago Airports

Chicago is home to two international airports—the huge O’Hare International Airport (ORD) and the smaller Chicago Midway International Airport (MDW). O’Hare is among the busiest airports in the country and sits about 14 miles from Chicago’s Loop. It’s a hub for both American Airlines and United Airlines, as well as a focus city for Frontier Airlines and Spirit Airlines. Midway Airport is about 12 miles from the Loop and a major base for Southwest Airlines.

How to Get to Chicago from O’Hare International Airport (ORD)

The Chicago Transit Authority’s rail network (known as the L) connects to O’Hare via the Blue Line. Travel time from the airport to the Loop is about 45 minutes and a ticket costs $5. Taxi fares to downtown Chicago are generally in the $40 range and rideshare options (like Lyft and Uber) start at around $35-50 for the 25-90 minute (depending on traffic) drive.

How to Get to Chicago from Chicago Midway International Airport (MDW)

The L also serves Midway Airport with the Orange Line. The trip from Midway to downtown takes about 25 minutes and a ticket costs $2.50. By car, the trip is 15-40 minutes (depending on traffic). Taxi fares start at around $25 and rideshare fares are about $25-40.

Where Else to Go from Chicago

Day Trips from Chicago

Starved Rock State Park.

Starved Rock State Park: About 90 minutes from the city you can hike sandstone canyons and visit waterfalls at Starved Rock State Park. 

Indiana Dunes National Park: Visit one of the nation’s newest national parks just 45 minutes from Chicago. Here you can hike sand dunes, swim in Lake Michigan, and spot rare bird species. 

Oak Park: Ten miles west of downtown Chicago, the suburban village of Oak Park is home to the Frank Lloyd Wright-Prairie School of Architecture District, the largest concentration of Frank Lloyd Wright homes in the country, as well as the architect’s studio. The Ernest Hemingway Birthplace and Museum is also here, along with numerous restaurants and boutiques. 

Where Else to Visit from Chicago

Milwaukee: Milwaukee is only 90 miles from Wisconsin, but there’s so much to do you’ll want to spend the night. Spend some time in the art museum, designed by Spanish architect Santiago Calatrava and drink your way through a few Wisconsin breweries. Don’t forget the cheese curds. 

Galena: About 160 miles from Chicago, Galena was once a major port city and today is a tourist town that boasts hundreds of buildings on the National Register of Historic Places, including the home of Ulysses S. Grant. The historic downtown is cute and full of shops and restaurants. In the winter, you’ll find some of Illinois’ only ski slopes in Galena. 

Books, Movies and TV Shows Set in Chicago 

Ferris Bueller’s Day Off: There are many movies filmed in Chicago, but this one is like a love letter to the city. Watch for scenes at Wrigley Field, the Art Institute of Chicago and plenty of great skyline shots. 

Hoop Dreams: This documentary follows two students recruited from the South Side of Chicago for a prestigious basketball program, and looks at issues of race, class, and education. 

The Devil In the White City: This book, based on a true story, tells the behind the scenes story of the 1893 World's Columbian Exposition from the view of designer Daniel Burnham, while also telling the story of serial killer H.H. Holmes.

Dreams From My Father: Barack Obama’s first book was published back in 1995, before he was a politician. It tells the story of his life, including many scenes in Chicago, where he worked as a community organizer at the time and met Michelle Obama. 

Previous cheap flights we've found to Chicago: 

  • Atlanta nonstop to Chicago for $97 roundtrip
  • Austin nonstop to Chicago for $118 roundtrip
  • Denver nonstop to Chicago for $387 roundtrip in lie-flat business class

Find your next cheap flight to Chicago—or anywhere—with amazing deals delivered right to your inbox.

character throwing a paper airplane
Treat your travel to cheap flights

Sign up for free to start getting flight alerts. Or upgrade to get 4x the deals, rare destinations, peak season tickets, and Mistake Fares. Either way, you’ll never overpay on flights again.

Sign up

Actual deals booked by our Premium members

New York City
get free flight alerts