Cheap Flights To Chicago (ORD)

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Cheap Flights to Chicago from $27 One Way, $54 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago ORD Flight Information

Traveling To
Destination Airport IATA Code
Number of Airlines Serving
Spirit Airlines, Frontier Airlines
Flight Price
Earliest Departing Flight
UA 2664 7:13AM EDT
Latest Departing Flight
AS 4509 Mar 27 9:53PM EDT

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Trump International Hotel & Tower Chicago
Hyatt Regency Chicago
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Bargain flights to Chicago are a good way to get you into a city that is full of art, culture, and history.

Flights to Chicago

Generally, flights to Chicago land at O'Hare International Airport, although Midway International Airport is gaining popularity. Midway International is located just 10 miles from the downtown center, and there are shuttle buses to hotels as well as the Transit Authority's Orange Line. Chicago flights that land at O'Hare International Airport put you about 17 miles northwest of the city, and transportation options include regional trains and buses, car rentals, and transit lines. Music in the terminals is listed and you can log into the airport website to find out exactly what you were hearing! Just be aware that if you do this from the airport, the available Wi-Fi is charged at $6.95 a day.

Chicago Weather

The term "Windy City" may actually refer to politicians' speeches, but that doesn't change the fact that the weather is often blustery. Whenever you visit, you will want to keep a jacket on hand for the lake breezes. Weather becomes nasty between November and March, especially in January, when temperatures drop to 24°F (-4°C), and are emphasized by that ubiquitous wind, as well as snow! Plan for indoor activities if you visit during this time period! You'll probably prefer the weather between April and October, when everyone rushes outside. During the peak tourist season, temperatures hover around 85°F (29°C).

Getting Around Chicago

Driving in downtown Chicago is a hassle best avoided. Traffic is overwhelming, pedestrians often don't follow the rules of the road, parking spaces are expensive, and tickets and towing are strict for violations, especially in the snow! The best way to get around Chicago is public transit. With several different agencies in the Chicago area all overseen by the RTA (Regional Transportation Authority), you can plan trips online with their planner. Once your Chicago flights have landed, navigating the city is easy. The city is consistent in street numbering and block lengths and organized on a grid that is easy to get used to. There are, however, some notable exceptions, avenues like Milwaukee and Ogden that go diagonally or meander through the city.

Chicago Attractions

Chicago is a bustling city, with many things to do and see within its city limits. Explore the arts, the night life, and even some natural areas to keep busy. Below are some suggestions to get you started:

  • The Adler Planetarium, with astronomy shows and neat interactive space exhibits.
  • DuSable Museum of African American History, with exhibits of the history and achievements of people of African descent in Chicago.
  • Rogers Park beach, with miles of sand to remind you that you're on the largest freshwater lake entirely in the United States.
  • Shedd Aquarium, with exhibits that cover the Caribbean and the Pacific Northwestern United States.
  • Milennium Park, with ice skating, cultural programs, and exhibitions in the new Chicago town square.

Chicago When to Go

Come summer, Chicagoans head to the beaches, parks, and festivals along Lake Michigan. A chill often lingers in the air in early summer, while late summer can be muggy. Regardless of the season, pack layers, as weather can fluctuate greatly. Summer also brings spikes in hotel rates.

Fall is pleasant until mid-November, when temperatures plunge, and spring doesn’t get reliably comfortable until late April. Anytime between May and November, you’ll be able to combine season-less indoor attractions with the convivial appeal of the outdoors at the lakefront, on Chicago River boats, and milling around Millennium Park.

Weather and prices are tradeoffs in Chicago. In January and February, the “hawk” (a local term for the harsh wind off Lake Michigan) sweeps down Michigan Avenue, and snow buries the streets. But hotel rates are bargain basement and attractions uncrowded.

Frequently asked questions

Am I currently able to fly to Chicago?
Before you book your fare, check out our Covid-19 Travel Advisor. This page contains all the facts about current travel advice, quarantine regulations and other essential information for your flight to Chicago.
If I am not able to travel because of COVID-19, can I change or cancel?
Before you purchase your tickets, check your preferred carrier’s terms and conditions. This should help with most questions regarding COVID-19 and changes to your flight. For more details, visit our Customer Service Portal.
Which airlines fly to Chicago?
With 20 airlines to select from, finding the perfect flight that matches your budget and plans will be easy. O’Hare Intl. Airport (ORD) is the main gateway to Chicago and where you’ll likely be disembarking. These popular international airlines are waiting to take you there:

  • United Airlines - 612 flights to Chicago per month
  • American Airlines - 339 flights to Chicago per month
  • Air Canada - 190 flights to Chicago per month

What is the best airport to fly to in Chicago?
Jump on a flight to Midway Intl. Airport (MDW) and get ready to explore the best of this city. The airport is around 9 miles southwest of the downtown area. Also research the price of flights to O’Hare Intl. Airport (ORD), which is another way to arrive at Chicago.
How much is a flight to Chicago?
The cost for a round-trip flight to Chicago this last week fluctuated from $54 to $97. If you were flying one-way out of Dallas (DFW), you could have scored fares from as low as $27.
How to book the cheapest flight to Chicago?
With some of the most exciting flight deals around, you can jet for less with Orbitz. The following hints and tips will help you snap up cheap flights to Chicago — and leave you with cash to spare:

  • Taking off from or landing at nearby airports can be more cost-effective. Type in your preferred departure and arrival airports. Next, click on the ‘Nearby airports’ function below to explore your options.
  • If you’re flexible with your travel itinerary, click on the ‘Show flexible dates’ option. It’ll bring up flight deals for the days either side of your selected departure. Airfares often vary depending on the day of the week.
  • Hit ‘Show options’ to refine your search results. You can choose your preferred airline and seating class here. Under ‘Sort & Filter’ to the left, you can even specify whether you want to fly in the morning, afternoon or evening.
  • Reserve your seat as soon as you’ve worked out your travel dates. While it does happen occasionally, airfares rarely fall in price as your date of departure approaches.
  • Bundle your hotels, flights and car rentals into a package deal and unlock great discounts. Save your hard-earned cash for things you’re really excited about, like discovering every corner of Chicago.
  • Flying during the busy season means steep airfares. Try to plan your trip outside of popular periods, such as school breaks, Thanksgiving and Easter.

How long is a flight to Chicago?
Where you’re leaving from and whether you have a layover help determine your flight time. However, these three top routes to Chicago will give you a clearer idea:

  • New York, NY (LGA-LaGuardia) to O’Hare Intl. Airport (ORD) - 2 hours and 40 minutes
  • Boston, MA (BOS-Logan Intl.) to O’Hare Intl. Airport (ORD) - 2 hours and 51 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to O’Hare Intl. Airport (ORD) - 2 hours and 13 minutes

What is the best time to book a flight to Chicago?
If you can, purchase your flights to Chicago in January. This is the best month to get low airfares, closely followed by February and August. With a little organizing, you’re guaranteed to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Chicago?
When it comes to cheap flights to Chicago, the best days to book are generally Tuesdays, Wednesdays and Saturdays. A rewarding flight deal is just clicks away with Orbitz.
What is the cheapest day of the week to fly to Chicago?
Consider departing early in the week if you want to get cheap flights to Chicago. Orbitz data from 2020 shows Monday is generally the most affordable day to set off, followed by Tuesday. Saturdays were shown to have the most expensive airfares. This is possibly because many travelers prefer to kick off their break after a long working week.
What is the cheapest month to fly to Chicago?
To secure cheap flights to Chicago, you should depart in August. If saving money on your plane ticket is your main concern, Orbitz data has found that this is generally the best month to take a trip. June is when airfares are the most expensive.
Which airlines allow free cancellation?
Life changes, and we believe your flight should be able to do the same. That’s why Orbitz makes it a cinch to search for airlines with no change fees and free cancellation. Simply enter your departure and arrival points and then select “Filter by flexible change policies.” How’s that for easy?
What do I need for the flight to Chicago?
Nothing’s more fun than flying off on an adventure, but it’s good to be prepared. This list of useful tips will help get your trip off to a flying start:

  • Whether you print it out at home or use an electronic one, you’ll need your boarding pass to walk on to the plane. You’ll also need some type of government-issued ID. If you’re traveling internationally, make sure your passport is valid and you’ve looked into visa requirements.
  • Take some activities to keep you amused on your trip to Chicago. Books and electronic gadgets like tablets and e-readers are ideal. Don’t forget to take a water bottle with you as well. Even on a short flight, it’s important to remain well-hydrated.
  • Even if you’re traveling when it’s sweltering outside, take a sweater or cardigan on board with you. Airplane cabins can get downright cold.

How many direct flights are there to Chicago?
Each month, there are 604 direct flights to Chicago. Choose from a nice variety of airline companies, including Southwest Airlines, Frontier Airlines and Delta Air Lines. Other carriers that fly to Chicago nonstop are Volaris, Porter Airlines and Allegiant Air.
How do I get cheap first-class/business deals to Chicago?
There are ways of booking first or business-class fares to Chicago that won’t burn a hole through your wallet. Snap up a seat in the pointy end of the plane for less with these great tips:

  • Being flexible isn’t just useful for your yoga. Avoid locking in your travel dates so you can pick up more affordable airfares when a sale pops up.
  • Look for a budget carrier that has seats in business class. They usually come with extra space and a glass of bubbly — and a nicer price.
  • Make the most of your airline’s customer loyalty program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in online auctions.

How to get into Chicago from the airport?
Step off the tarmac at Midway Intl. Airport (MDW) and then grab the keys from one of two Midway Intl. Airport (MDW) car rental companies on-site, Budget or Avis. With a sweet set of wheels, getting to the downtown area of Chicago from MDW will be a cinch. All you have to do is set your GPS and cruise 9 miles to the northeast. You could also use public transportation or take a taxi into town and rent a set of wheels directly from the city center. Check out the deals available on our Chicago car rentals.
What is the best time to go to Chicago?
You’ll have all the fun you can handle no matter what time of year you visit Chicago, but are the most popular months. Like to pack your schedule with warm-weather adventures? Book your getaway close to June 20. This is when the summer season kicks off in the Northern Hemisphere. Expect the mercury to range between 65undefined and 75undefined during this time of year.
Travel tips for Chicago

  • Slip on your comfortable kicks and tour this city on foot. There are tons of terrific attractions to make your way to, such as McCormick Place and Millennium Park.
  • You’ll discover rewarding day trip adventures a quick drive from Chicago’s center. Check out Wrigley Field first and after that, University of Chicago.
  • When you want to get out and experience more of Illinois, organize a car rental and drive to Rockford. Bloomington is another interesting city with so much to do and see.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.