$126 Cheap Flights from Lubbock (LBB) to Chicago (MDW)

View $126 flight on Wed, Dec 3, 2025Opens in a new window

Popular airlines from Preston Smith Intl. Airport (LBB) to Chicago Midway Airport (MDW)

Cheap Flights from Lubbock to Chicago (LBB-MDW)

Prices were available within the past 7 days and start at $126 for one-way flights and $268 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Nov 5 - Thu, Nov 6
LBB
Lubbock
MDW
Chicago
$268 Roundtrip, found 4 days ago
$268
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Lubbock to Chicago, returning Thu, Nov 6, priced at $268 found 4 days ago
Southwest Airlines
Wed, Nov 5 - Thu, Nov 6
LBB
Lubbock
MDW
Chicago
$273 Roundtrip, found 4 days ago
$273
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Lubbock to Chicago, returning Thu, Nov 6, priced at $273 found 4 days ago
Southwest Airlines
Wed, Nov 5 - Thu, Nov 6
LBB
Lubbock
MDW
Chicago
$278 Roundtrip, found 4 days ago
$278
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Lubbock to Chicago, returning Thu, Nov 6, priced at $278 found 4 days ago
Southwest Airlines
Mon, Dec 8 - Thu, Dec 11
LBB
Lubbock
MDW
Chicago
$285 Roundtrip, found 5 days ago
$285
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Dec 8 from Lubbock to Chicago, returning Thu, Dec 11, priced at $285 found 5 days ago
Southwest Airlines
Mon, Dec 8 - Thu, Dec 11
LBB
Lubbock
MDW
Chicago
$290 Roundtrip, found 5 days ago
$290
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Dec 8 from Lubbock to Chicago, returning Thu, Dec 11, priced at $290 found 5 days ago
Southwest Airlines
Wed, Nov 5 - Fri, Nov 7
LBB
Lubbock
MDW
Chicago
$302 Roundtrip, found 4 days ago
$302
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Lubbock to Chicago, returning Fri, Nov 7, priced at $302 found 4 days ago
Southwest Airlines
Sat, Dec 13 - Mon, Dec 15
LBB
Lubbock
MDW
Chicago
$306 Roundtrip, found 2 days ago
$306
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Dec 13 from Lubbock to Chicago, returning Mon, Dec 15, priced at $306 found 2 days ago
Southwest Airlines
Wed, Nov 5 - Fri, Nov 7
LBB
Lubbock
MDW
Chicago
$307 Roundtrip, found 4 days ago
$307
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Lubbock to Chicago, returning Fri, Nov 7, priced at $307 found 4 days ago
Southwest Airlines
Sat, Dec 13 - Mon, Dec 15
LBB
Lubbock
MDW
Chicago
$311 Roundtrip, found 2 days ago
$311
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Dec 13 from Lubbock to Chicago, returning Mon, Dec 15, priced at $311 found 2 days ago
Southwest Airlines
Wed, Nov 5 - Fri, Nov 7
LBB
Lubbock
MDW
Chicago
$312 Roundtrip, found 4 days ago
$312
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Lubbock to Chicago, returning Fri, Nov 7, priced at $312 found 4 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $419
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $419

Frequently asked questions

How much does a flight from Preston Smith Intl. Airport (LBB) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $126 or cheap return flight from $268 from Preston Smith Intl. Airport (LBB) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Preston Smith Intl. Airport (LBB) to Midway Intl. Airport (MDW)?
November is the cheapest month to fly from LBB to MDW. Traveling outside of peak seasons is often the key to finding a great deal.
What is the cheapest airline that flies from Preston Smith Intl. Airport (LBB) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from LBB to MDW, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Preston Smith Intl. Airport (LBB) to Midway Intl. Airport (MDW)?
You'll need to catch a flight with a layover if you're traveling from Preston Smith Intl. Airport (LBB) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from LBB to MDW?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Preston Smith Intl. Airport (LBB) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) on schedule, opt for a flight that leaves from Preston Smith Intl. Airport (LBB) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Preston Smith Intl. Airport (LBB) to Midway Intl. Airport (MDW) last-minute?
Waiting until just before your trip to book a flight from LBB to MDW generally means paying more. While it's possible to find some last-minute discounts, they're not always guaranteed. Allow some flexibility in your schedule for the best chance of getting a bargain.
Is it cheaper to book a LBB to MDW flight and hotel package?
Booking a LBB to MDW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Choose from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Preston Smith Intl. Airport (LBB) to Midway Intl. Airport (MDW)?
In most instances, you're able to cancel or reschedule your LBB to MDW flight. However, there may be additional fees, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's fees and rules on flight changes, or if you'd like more details, head to our Customer Service portal.

Travel information

Travel information

Origin airport
Preston Smith Intl.
Destination airport
Midway Intl.
Airlines serving
Southwest Airlines
Roundtrip price
$267
Distance
950 mi

Book with confidence

Book with confidence

Lubbock to Chicago Flights

The cheapest times to fly from Lubbock to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Lubbock to Chicago are during the month of November. You can find some of the cheapest flights from Lubbock to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Lubbock to Chicago

Sunday is one of the best days to book for cheap flights from Lubbock to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Lubbock to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Lubbock to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $126 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Lubbock to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Lubbock to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Lubbock to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.