Flights to Chicago

Compare Cheap Flights to Chicago, USA

Don’t spend a fortune on flights to Chicago. Webjet helps you find the best deals on some of the region’s top airlines, so you can spend less on airfare and more on your American adventure.

Chicago Guide

Compare Cheap Flights to Chicago, USA

For an on-the-go holiday in a unique city, check out cheap flights to Chicago, USA. Chicago, coined the Windy City, is the third most populous city in the United States, behind New York and Los Angeles. Known for its intricate architecture, Chicago is considered the birthplace of the skyscraper. Once you arrive in Chicago, you’ll see why. In addition to architecture, Chicago is known for its art, food, entertainment, and sports teams.

No matter which New Zealand city you’re coming from, you’ll have no trouble finding cheap flights to Chicago. Lots of airlines offer cheap airfares to Chicago, including Qantas, United Airlines, American Airlines, and Fiji Airways. If you are flying from Auckland, Wellington, Christchurch, or Queenstown, you can score flights to Chicago with only one stopover. If you are travelling from a smaller city, you can expect two quick stopovers on your way to Chicago. Every day, there are around 70-80 flights from each Auckland, Wellington, and Christchurch, and about 40 from Queenstown. Flights to Chicago average about 17 hours from Auckland, 20 hours from Wellington, 20 hours from Christchurch, and 22 hours from Queenstown. You could also plan a long stopover, so you can spend a day exploring a new city between flights. Common stopover cities for cheap flights to Chicago include Los Angeles, Houston, Melbourne, Sydney, and Brisbane.

Are you ready to start planning your holiday with cheap flights to Chicago, USA? Webjet compares cheap airfares to Chicago from all different airlines to help you find the best deals on flights. Book your cheap flights to Chicago with Webjet, and then use our travel guide to plan out how you’ll spend your American adventure.

Best time to visit Chicago

When should you book cheap airfares to Chicago?

The best times to visit Chicago are in the spring, from April to May, and autumn, in September and October. During these months, the temperatures are warm yet the crowds are manageable. The summer time is peak season, since the weather is at its warmest and Chicago hosts multiple festivals between June and August. If you decide to visit at this time, be sure to book your flights and hotel early to lock in a good deal.

From November to March, Chicago has notoriously cold winters with lots of snow. It’s called the Windy City, after all. Temperatures can hit as low as -13 degrees, so you’ll need to bundle up if you decide to visit at this time. However, the hotel and flight deals are hard to beat during the off-peak season.

Airports in Chicago

Arriving in Chicago

Chicago is home to two major airports. O’Hare International Airport is the larger of the two and is located in the Northwest side of Chicago, approximately 23 km outside the city centre. The airport has five terminals, three of which are used for international travel. Terminal 1 and 3 are used for outbound international flights, while Terminal 5 is the arrival destination for international planes. Midway International Airport is about 13 km southwest of the city centre. Midway airport operates mainly domestic flights, but you may arrive to this airport if you have a stopover in another US city.

Getting to the city centre from Chicago O’Hare International Airport (ORD)

The CTA, Chicago’s train system, is the cheapest way to get to downtown Chicago from the airport. Catching the Blue line costs about $5 USD and will take about 45 minutes to get you from O’Hare to the Loop. If your hotel is in the Loop, you’ll be a quick walk away. Otherwise, you can transfer trains in the city centre to get to a station closer to your accommodations.

If you don’t mind splurging, you can take a taxi from O’Hare to your hotel. A taxi won’t be as cost-efficient as public transportation, as it will set you back about $40 USD (plus extra for a tip). To get to the Loop, a taxi will take about 35 minutes. Depending on the location of your lodging, it may take more or less time than that to arrive.

Getting to the city centre from Midway International Airport (MDW)

The cheapest way to get to downtown Chicago from Midway Airport is by taking the Orange Line, coined the “L” train, as it is elevated. One-way fare on the “L” train costs $2.50 USD. Unlike much of the CTA, the Orange Line is not open 24 hours, but it is open between 4AM and 1AM every day. The train from Midway Airport to downtown Chicago takes between 20-25 minutes.

Airport shuttles are a convenient way to get from the airport to your hotel in downtown Chicago. They operate every 10-15 minutes until 10:30PM. Although shuttles are typically cheaper than taxis and Ubers, they aren’t quite as affordable as public transportation. Exact costs vary based on the time of travel and the hotel destination.

A taxi will get you from Midway Airport into the city centre in about 20-25 minutes. Both taxis and Ubers are available from the airport. Taxi fare into the city costs about $30, while you can get an Uber ride for about $20 or less.

Things to do in Chicago

Things to do in Chicago

Millennium Park

One of the most spectacular urban parks in the world is Millennium Park, one of Chicago’s most popular sites. Located in the Loop, the central section of the city, Millennium Park houses modern art structures and sculptures. The most famous among them, Cloud Gate, more commonly referred to as the Bean, is a massive reflective structure that attracts millions of visitors every year. Other spectacles in Millennium Park include the Crown Fountain, Lurie Garden, and Wrigley Square.

Art Institute of Chicago

If you didn’t know already, Chicago is highly celebrated for its art scene. The Art Institute of Chicago, by the Loop, is one of the largest art museums in the United States. Its incredible exhibitions house some of the most popular works of American art, including Nighthawks and American Gothic, as well as famous European works like Seurat’s A Sunday Afternoon on the Island of La Grande Jatte and Picasso’s The Old Guitarist. Adult admission is $25 USD, but students, teens, and seniors can pay a discounted price of $19 USD.

Wrigley Field

Sports lovers and fair-weather fans alike will enjoy a trip to Wrigley Field, located on the North Side of the city. This historical baseball field has been in use for more than 100 years, used by the Chicago Cubs. It’s particularly exciting to visit this landmark since the Cubs broke the “Curse of the Billy Goat,” a superstition that kept the Cubs from winning a World Series game between 1945 and 2016. If the Cubs are in town, you should try to catch a home game to experience America’s favourite pastime. If baseball is not in season or the Cubs are playing in another city, you can take a guided tour of Wrigley Field for $25 USD.

See a Second City Show

If you love live comedy, you might consider ordering tickets to a Second City show. One of the most celebrated improv comedy clubs in the United States, Second City started the careers of many American comedians and actors, such as Tina Fey, Steve Carell, Bill Murray, and Amy Poehler. Disclaimer: Your face and abs might be sore from laughing so hard during the show. Since Second City is a bit of a walk from any Metro stops, you might consider getting to the theatre by a taxi or ride-sharing service, such as Uber or Lyft.

Lincoln Park Zoo

Lincoln Park Zoo is unique for two reasons: it is one of the oldest zoos in the United States and it is one of the only free zoos in the country. For no cost, you can gaze at the lions, tigers, giraffes, monkeys, and other endearing creatures. The zoo is located in Chicago’s North Side, so you may need to take the Metro if you are staying in the city centre.

Navy Pier

The Navy Pier is Chicago’s number one tourist attraction. Located on the shoreline of Lake Michigan, the pier offers travellers a gorgeous view of the water and a fun-packed night of amusement park rides. You can enjoy a meal or drinks at one of the many restaurants or bars in the area, or you can take a ride on the Ferris wheel or carousel. It’s a fun time for couples, solo travellers, or families, with a variety of attractions suitable for all audiences.

Eat the Chicago staples

A trip to Chicago isn’t complete without indulging in some of Chicago’s popular dishes. One of these meals is deep-dish pizza, a thicker version of a classic pizza, which places meat and veggie toppings inside the pizza rather than on top. For the best deep-dish pizza, you can go to the classic spots, Giordano’s and Lou Malnati’s, or try out a local hole-in-the-wall restaurant. Another specialty, Chicago Dogs, are tasty hot dogs topped with mustard, tomato slices, white onions, relish, a pickle spear, capsicums, and celery salt. You can order Chicago-style hot dogs at most eating establishments, but Portillo’s is the most popular place to order this delicacy.

Take in the view from the top of the Signature Room

For a gorgeous view of the Chicago skyline, take the elevator up 95 floors to the Signature Room, a cocktail lounge and restaurant at the top of the John Hancock Tower. Many tourists opt to climb to the top of the Willis Tower, but for the cost it takes to climb this tower, you can indulge in a cocktail at the Signature Room. It’s gorgeous at all hours of the day, but it is especially breathtaking at sunset, when the skies are pink and the skyline glows as the sun descends.


If weather permits, a walk along the Riverwalk is a relaxing way to explore Chicago’s stunning architecture. There are plenty of restaurants, bars, and shops that line the Riverwalk, so you can stop for a much-needed beverage or snack if need be. Since the Chicago River runs right through the Loop area of the city, you won’t need to travel off the beaten path to get to the Riverwalk from the other popular sites.