$22 Cheap Flights to Southwest Side, IL

Frequently Asked Questions

What month is the cheapest to fly to Southwest Side?

The cheapest month to fly to Southwest Side is December when demand is low. Off-peak months are often when you'll find cheap fares. To save money, steer clear of flying during public holidays and school breaks.

Which US cities have the cheapest flights to Southwest Side?

New York, Washington and Dallas usually offer cheap flights to Southwest Side. Keep in mind that fares vary based on factors like demand, holiday periods and number of stopovers.

Which US cities fly direct to Southwest Side?

There are 150 US destinations that you can fly to Southwest Side nonstop from. Compare your options by using the "Direct flights only" filter on Expedia and pick the ideal starting point for your trip. Here are a handful of the leading cities to head out from:

• New York
• Washington
• Dallas
• Boston
• Phoenix

How to find a cheap flight to Southwest Side?

Book your trip early for the best chance of scoring cheap flights to Southwest Side. Also, consider traveling during off-season months like January and February. If you leave on a Thursday, you can save 16% on average compared to departing on a Sunday.* Save time checking every day and set up a price alert on the Expedia app. We'll send you a notification when fares change.

*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.

How to get a cheap last-minute flight to Southwest Side?

Staying flexible about your plans can help you to find last-minute offers on cheap flights to Southwest Side. To view all the available options, try exploring different ticket types, changing your Southwest Side trip dates, flying out of an alternative airport or going with another carrier.

How far in advance should I book a flight to Southwest Side?

Find the departure dates you want and a fare your budget will love by booking your domestic flight to Southwest Side up to 28 days in advance. Search for tickets between two and four months ahead if you're jetting to Southwest Side from an international destination.*

*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.

Which day of the week is the cheapest day to buy a plane ticket to Southwest Side?

You can generally find cheap flights to Southwest Side on a Sunday. You'll save about 8% on average compared to those who book on a Friday, which is often the most expensive day to buy tickets.*

*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.

Which airlines fly to Southwest Side?

Book a seat with one of these airlines and the vibrant region of Southwest Side will be all yours to discover:

• United Airlines - 13,391 flights to Southwest Side each month, including 13,391 flights to O'Hare Intl. Airport (ORD) per month.
• American Airlines - 10,417 flights to Southwest Side each month, including 10,417 flights to O'Hare Intl. Airport (ORD) per month.
• Delta Air Lines - 1,213 flights to Southwest Side each month, including 1,213 flights to O'Hare Intl. Airport (ORD) per month.

Where do you fly into Southwest Side?

When you're flying to Southwest Side, the main airport to touch down at is Midway Intl. Airport (MDW). You can also head to nearby hubs like O'Hare Intl. Airport (ORD), Lewis University Airport (LOT) or Gary, IN (GYY-Gary - Chicago Intl.). Another option to keep in mind when you fly to Southwest Side is Chicago Executive Airport (PWK).

Can I save money by booking a Southwest Side trip package?

Bundle your flights and accommodations and you could save hundreds of dollars. Better still, you can add extras like activities and car rentals to your Southwest Side flight and hotel package deal. With Expedia, it's a breeze to book all your Southwest Side travel plans in the same place.

Can I change or cancel my flight to Southwest Side?

You can typically change or cancel your flight to Southwest Side within 24 hours of booking. However, keep in mind that some flights are non-refundable. In those cases, you may receive a credit toward future travel instead of a direct refund. Be sure to check the airline's terms and conditions in your itinerary for exact details. Use Expedia's "Changes included" or "No cancel fee" filters during your search to secure cheap flights to Southwest Side with flexible change policies. For additional information, head to our Customer Service Portal.