Book Cheap Flights to Chicago (ORD)

All round-trip airfares listed under the best deals for Chicago flights include fuel surcharges, service fees, and applicable taxes. While Skytripfare provides a Lowest Fare Guarantee, flight ticket prices are subject to change at the time of booking based on availability and demand from the airline or supplier. Skytripfare does not have control over these fluctuations.

Lying along the shores of Lake Michigan, Chicago, the Windy City, attracts global tourists with its vibrant scenes, exciting architecture, numerous cultural attractions, and excellent shopping. Beyond the city’s popularity in the sporting sphere, the mesmerizing beaches, and the waterfront, the city has much to offer its travelers to fulfill their exploring desires. Travelers and explorers love the big city life, unique neighborhoods, mouthwatering cuisines, and Midwest charm. 

You can eat, play tournaments, party, relax, and even indulge in watersports like snorkeling and scuba diving. The city’s most-visited cultural institutions include the Art Institute of Chicago, Adler Planetarium, and the Field Museum. You can also take a boat tour of Chicago’s famous skyscraper’s like Tribune Tower and Willis Tower. The easy availability of flights to Chicago globally made the city ideal for sports, relaxation, and excitement.

With Skytripfare, you get plane tickets to Chicago at the best prices. You can search for the airlines offering services to the city along with their seat descriptions and other amenities during the journey. Explore different seat options and in-flight perks to make your journey as comfortable as possible. Skytripfare also provides real-time flight tracking, ensuring you're always in the loop. Chicago's vibrant culture, iconic architecture, and deep-dish pizza await you. Let Skytripfare be your ticket to an unforgettable escapade. Book now and get ready to create cherished memories in the Windy City!

O’Hare serves 44 airlines. Some of these include:

Chicago experiences a continental climate with warm summers, cold winters, and frequent fluctuations in temperature, cloudiness, humidity, and wind direction. Some travelers love exploring the city during the spring. It is when the temperatures start increasing, offering a pleasant experience. 

If you want to explore the culture of the city through its various festivals, events, and concerts, you can visit the city during the summer months.  The summer months in Chicago do bring warmer temperatures and higher humidity levels. It's all part of the unique experience that the city has to offer, and with a little preparation, you can make the most of your time exploring and enjoying the rich cultural scene that Chicago has to offer.

The best season to visit the Windy City is during the fall. You can experience the same outdoor activities, including outdoor festivals and outdoor dining, that take place during the summers. If you're planning to explore Chicago, now's a good moment to grab your tickets. You might even find some cheap flights to Chicago for a great budget-friendly trip.

The following tips will help you can find the cheapest flight in Chicago.

Book your flight in advance: Buying airline tickets to Chicago at least two weeks in advance is best since the prices might rise as you move close to the departure date.

Fly mid-week: It is best to travel mid-week, which is between Tuesday and Thursday. Since more people fly on weekends, you might experience a surge in airfares at that time.

Opt for budget airlines: Choose a budget airline or low-cost carrier. They offer cheaper flight tickers compared to their full-service counterparts.

Season: Avoid traveling in the peak time of the year, which is usually during the months between May and July. It is because the fare of the tickets is higher due to an increase in demand.

Chicago has over 70 neighborhoods, a robust lineup of festivals, a sprawling waterfront, and charming parks and walkways. The city has something for every traveler. Enlisted are some of the things that you must do when visiting Chicago.

1. Enjoy a 360-degree view of Chicago

Visit one of the tallest buildings of the Chicago skyline, the John Hancock Building, and take an elevator up to the 94th floor. Visit 360 Chicago, an observational deck that lets you enjoy the mesmerizing 360 degrees view of the city. The place has a bar where you can grab your drink and enjoy the view. If you want more adventure, explore the TILT, a platform made from glass and steel. You can experience the platform tilting outwards. You can see the breathtaking view of the Magnificent Mile lying 300 meters below.

2. Shopping at Magnificent Mile

If you are a shopaholic, one of the most incredible things to do is to walk around the city’s most famous shopping area. You can spot famous landmarks along the avenue, including the Wrigley Building, Chicago Water Tower, and the John Hancock Center.

3. Stroll along Chicago Riverwalk

Besides Millennium Park, you can also visit the iconic Chicago Riverwalk, where you can take a leisurely walk along the picturesque river flowing through the city. Do not forget to visit a museum dedicated to the Chicago River or explore an art gallery throughout the trail. If you want adventurous experiences, opt for a Chicago River kayak tour.

4. Wander around the Old Town and Visit its Most Beautiful Café

Besides exploring downtown, you can also explore the Victorian-era buildings in the gorgeous neighborhood of Old Town. The area is famous for its quaint streets, old-school pubs, old shops, and artisanal cafés.

5. Look Down at the City from Willis Tower Skydeck

Chicago has several tall skyscrapers, and the tallest one is the Willis Tower. The 440-meter-high tower built in 1973 remained the tallest building for almost 25 years. Climb the 103rd floor to the observation deck, popularly known as the Skydeck, where you can see the city through the glass balconies.

6. Admire the Skyline from North Avenue Beach

Ensure to make your way to North Avenue Beach, one of the most favorite places in the Windy City. Situated in Lincoln Park, the beach is a hotspot for swimmers, sunbathers, and volleyball players. Enjoy the breathtaking skyline view and its reflection on the water.

With various transportation options, navigating the Windy City is convenient. You can easily avail of rental cars, taxis, and buses to explore the city. Moreover, several hotels offer shuttle services for guests’ convenience. You must remember that cabs are expensive when not tied to hotels. Therefore, it is essential to crosscheck license plate numbers against permits.

Q.1 How can I get to the city center from O’Hare airport?

Chicago offers a well-developed public transport system, making it easier for travelers to transfer between the city center and the airport. Board the L train from the Metro station at the Chicago O’Hare Airport, and you will reach the city center within 45 minutes. Alternatively, you can take the PACE bus lines passing through the city center.

Q.2 How early should I book a flight to Chicago?

You must book your flight at least 60 days before your departure date. If you book your flight to your departure date, the flight will be expensive.

Q.3 Which day is the best to book a flight to Chicago?

Booking your flight in mid-week, which is Tuesday through Thursday, is the best option to book cheap flights to Chicago.

Q.4 What is the best time to fly to Chicago?

Take a morning flight, as they are the cheapest. The midday flight is usually more expensive.

Q.5 What can I do at the Chicago O’Hare Airport?

The airport offers exciting options for travelers having a long layover in Chicago or arriving early for their flights. Explore the murals and sculptures displayed around the airport. Visit the Hilton Health Club offering a large gym, a sauna, and a swimming pool.

Q.6 What is the coldest month in Chicago?

January tends to be the coldest month experiencing maximum snowfall every year. The temperatures are between 26° F and 36° F.