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

Jan. 01, 2022
4 min read
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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.

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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 image by (Photo Courtesy of Ryan Patterson/The Points Guy)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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TPG featured card

Best card for premium perks while traveling
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards

2 - 10X points
10XEarn unlimited 10X miles on hotels and rental cars booked through Capital One Travel
5X5X miles on flights booked through Capital One Travel.
2X2 Miles per dollar on every purchase, every day

Intro offer

75,000 bonus miles
Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel

Annual Fee

$395

Recommended Credit

740-850
Excellent
Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

Why We Chose It

The Capital One Venture X card is one of the best all-round travel credit cards ever launched. Not only is it offering a tremendous welcome bonus, but cardholders can earn tons of miles on everyday spending and receive a 10,000-mile anniversary bonus to boot. Its annual fee is $395, but cardholders can count on up to $300 in statement credits toward travel booked through Capital One Travel each year and other valuable benefits like access to Priority Pass lounges and Capital One’s own growing family of airport lounges.

Pros

  • Excellent welcome offer worth 75,000 miles after you spend $4,000 on purchases in the first three months.
  • Up to $300 in annual travel statement credits toward bookings make through Capital One Travel.
  • 10,000 bonus miles (worth $100 toward travel) each account anniversary.

Cons

  • The $395 annual fee might be expensive for some, but this card’s benefits provide much more value than that.
  • If you don’t travel frequently, this might not be the best card for you.
  • Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel
  • Receive up to $300 back annually as statement credits for bookings through Capital One Travel, where you'll get Capital One's best prices on thousands of options
  • Get 10,000 bonus miles (equal to $100 towards travel) every year, starting on your first anniversary
  • Earn unlimited 10X miles on hotels and rental cars booked through Capital One Travel and 5X miles on flights booked through Capital One Travel
  • Earn unlimited 2X miles on all other purchases
  • Unlimited complimentary access for you and two guests to 1,400+ lounges, including Capital One Lounges and our Partner Lounge Network
  • Receive up to a $100 credit for Global Entry or TSA PreCheck®
  • Use your Venture X miles to easily cover travel expenses, including flights, hotels, rental cars and more—you can even transfer your miles to your choice of 15+ travel loyalty programs
  • Named editors' choice for "Best New Credit Card of 2021" by The Points Guy
  • Earn 10 miles per dollar when you book on Turo, the world's largest car sharing marketplace, through May 16, 2023
Best card for premium perks while traveling
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards Rate

10XEarn unlimited 10X miles on hotels and rental cars booked through Capital One Travel
5X5X miles on flights booked through Capital One Travel.
2X2 Miles per dollar on every purchase, every day
  • Intro Offer
    Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel

    75,000 bonus miles
  • Annual Fee

    $395
  • Recommended Credit
    Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

    740-850
    Excellent

Why We Chose It

The Capital One Venture X card is one of the best all-round travel credit cards ever launched. Not only is it offering a tremendous welcome bonus, but cardholders can earn tons of miles on everyday spending and receive a 10,000-mile anniversary bonus to boot. Its annual fee is $395, but cardholders can count on up to $300 in statement credits toward travel booked through Capital One Travel each year and other valuable benefits like access to Priority Pass lounges and Capital One’s own growing family of airport lounges.

Pros

  • Excellent welcome offer worth 75,000 miles after you spend $4,000 on purchases in the first three months.
  • Up to $300 in annual travel statement credits toward bookings make through Capital One Travel.
  • 10,000 bonus miles (worth $100 toward travel) each account anniversary.

Cons

  • The $395 annual fee might be expensive for some, but this card’s benefits provide much more value than that.
  • If you don’t travel frequently, this might not be the best card for you.
  • Earn 75,000 bonus miles when you spend $4,000 on purchases in the first 3 months from account opening, equal to $750 in travel
  • Receive up to $300 back annually as statement credits for bookings through Capital One Travel, where you'll get Capital One's best prices on thousands of options
  • Get 10,000 bonus miles (equal to $100 towards travel) every year, starting on your first anniversary
  • Earn unlimited 10X miles on hotels and rental cars booked through Capital One Travel and 5X miles on flights booked through Capital One Travel
  • Earn unlimited 2X miles on all other purchases
  • Unlimited complimentary access for you and two guests to 1,400+ lounges, including Capital One Lounges and our Partner Lounge Network
  • Receive up to a $100 credit for Global Entry or TSA PreCheck®
  • Use your Venture X miles to easily cover travel expenses, including flights, hotels, rental cars and more—you can even transfer your miles to your choice of 15+ travel loyalty programs
  • Named editors' choice for "Best New Credit Card of 2021" by The Points Guy
  • Earn 10 miles per dollar when you book on Turo, the world's largest car sharing marketplace, through May 16, 2023