Southwest deal alert: Book flights to Chicago for just 2,655 miles one-way

Jan 1, 2022

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Looking to snag a cheap flight to the Windy City? Now’s your chance — assuming you’ve got some spare Southwest Rapid Rewards miles laying around.

Southwest Airlines currently is running a sale on flights booked with miles between Chicago’s Midway International Airport (MDW) and more than two dozen U.S. cities, with one-way fares starting at just 2,655 miles.

TPG currently values Southwest miles at 1.5 cents each, which means Southwest is giving away these flights for as little as $39.83 worth of miles.

The very lowest fares appear to be for flights to Chicago from Boston (BOS); Providence, R.I. (PVD); Fort Lauderdale, Florida (FLL); and Miami (MIA) during the first couple months of the year. Flights between Chicago and Dallas (DAL) and New York (LGA) at the start of the year also are noticeably low.

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This deal was originally sent out by Thrifty Traveler Premium, which for $7.99 monthly or $49.99 annually, will send news of cheap flights, award flight sales and business-class deals straight to your email.

Deal basics

Airline: Southwest Airlines.
Routes: Between Chicago (MDW) and more than two dozen cities, including ATL/BWI/BOS/CVG/COS/DAL/DEN/FLL/IAH/MCI/LAS/LAX/MIA/MSY/LGA/MCO/SAN/TPA.
How to book: Directly through the airline’s booking page.
Travel dates: Now through Sept. 5 (the last day for which Southwest flights currently are available). But the lowest fares are clustered in January and February.
Book by: There doesn’t appear to be an end date for the sale. But it’s likely the lowest mile fares will disappear fast.

Sample flights

To find dates with the lowest fares, I recommend starting at Southwest’s Low Fare Calendar page and using it in one-way mode. Plug in your departure city, set Chicago (MDW) as your destination, pick a departure month and then hit ‘Search.’

Once you’ve found an inexpensive outbound flight, you can circle back and play around to find a low-cost return flight. Or you can search for an outbound flight and return flight at the same time using the “round-trip” mode using the calendar.

Screenshot courtesy of Southwest.

Some of the best one-way deals I found in the sale include:

  • Boston (BOS) to and from Chicago (MDW), for 2,655 miles.
  • Providence (PVD) to and from Chicago (MDW), for 2,655 miles.
  • Dallas (DAL) to and from Chicago (MDW), for 3,427 miles.
  • Miami (MIA) to and from Chicago (MDW), for 2,655 miles.
  • Fort Lauderdale (FLL) to and from Chicago (MDW), for 2,655 miles.
  • New York (LGA) to and from Chicago (MDW), for 3,427 miles.
  • Orlando (MCO) to and from Chicago (MDW), for 3,813 miles.
  • Tampa (TPA) to and from Chicago (MDW), for 3,813 miles.
  • Seattle (SEA) to and from Chicago (MDW), for 4,971 miles.
  • Atlanta (ATL) to and from Chicago (MDW), for 3,813 miles.

Related: TPG releases brand-new points calculator to make award bookings easier

As noted above, TPG currently values Rapid Rewards points at 1.5 cents each, and you can use our new Awards vs. Cash Calculator to determine whether a deal is a better value in cash or points.

Maximize your purchase

Taxes and fees on these miles fares will come to $5.60, one-way. While that’s not all that much, it still pays to use a card that earns points on airfare purchases, such as The Platinum Card® from American Express (5x on airfare booked directly with the airline or through American Express Travel, on up to $500,000 on these purchases per calendar year), Citi Prestige® Card (5x on airfare), Citi Premier® Card, Chase Sapphire Reserve (3x on airfare), American Express® Gold Card (3x on airfare when booked directly with the airline or via Amex Travel) or the Chase Sapphire Preferred Card (2x on travel). Or, use your Southwest Rapid Rewards Premier Credit Card for 3x on Southwest Airlines purchases. Check out this post for more on maximizing airfare purchases.

The information for the Citi Prestige Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Screenshot courtesy of Southwest.

Bottom line

You’ll want to move fast to grab the low miles fares to and from Chicago that are part of this deal. It’s not every day you can snag a flight to the city for under 3,000 miles.

Featured photo by Ryan Patterson/The Points Guy.

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