Southwest deal alert: Book flights to Chicago for just 2,655 miles one-way
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.
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.
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.
Top offers from our partners
How we chose these cards
TPG featured card
Rewards
| 3X | Earn 3X Miles on Delta purchases and purchases made directly with hotels. |
| 2X | Earn 2X Miles at restaurants worldwide, including takeout and delivery in the U.S. and at U.S. supermarkets. |
| 1X | Earn 1X Miles on all other eligible purchases. |
Intro offer
Annual Fee
Recommended Credit
Why We Chose It
Build your loyalty to Delta by applying for the carrier's mid-tier card option, the Delta SkyMiles Platinum card. The annual fee is quickly recouped by the card's travel perks, such as an application credit to Global Entry or TSA Precheck, annual companion certificate and so much more. Plus you can fast-track to elite status simply through card spend.Pros
- Earn bonus Medallion® Qualification Miles (MQMs) and an Medallion Qualifying Dollar (MQD) waiver when you hit specific spending thresholds with your card within a calendar year
- Receive a Domestic Main Cabin round-trip companion certificate each year
- Statement credit for TSA PreCheck/Global Entry fee (up to $100)
- First checked bag free
Cons
- Doesn't make sense if you don't fly Delta
- SkyMiles aren't the most valuable airline currency
- Earn 90,000 bonus miles after you spend $4,000 in purchases on your new Card in your first 6 months.
- Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. Payment of the government imposed taxes and fees of no more than $80 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
- Enjoy your first checked bag free on Delta flights. Plus enjoy Main Cabin 1 Priority Boarding and settle into your seat sooner.
- New: Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
- Earn 3X Miles on Delta purchases and purchases made directly with hotels.
- Earn 2X Miles at restaurants worldwide including takeout and delivery in the U.S., and at U.S. supermarkets.
- Earn 1X Mile on all other eligible purchases.
- Enjoy a per-visit rate of $50 per person for Card Members and up to two guests to enter the Delta Sky Club when traveling on a Delta flight.
- Fee Credit for Global Entry or TSA PreCheck® after you apply through any Authorized Enrollment Provider. If approved for Global Entry, at no additional charge, you will receive access to TSA PreCheck.
- Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs up to two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
- No Foreign Transaction Fees.
- $250 Annual Fee.
- Terms Apply.
- See Rates & Fees
Rewards Rate
| 3X | Earn 3X Miles on Delta purchases and purchases made directly with hotels. |
| 2X | Earn 2X Miles at restaurants worldwide, including takeout and delivery in the U.S. and at U.S. supermarkets. |
| 1X | Earn 1X Miles on all other eligible purchases. |
Intro Offer
Earn 90,000 bonus miles after you spend $4,000 in purchases on your new Card in your first 6 months.Earn 90,000 Bonus Miles50,000 Bonus MilesAnnual Fee
$250Recommended 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.670-850Excellent/Good
Why We Chose It
Build your loyalty to Delta by applying for the carrier's mid-tier card option, the Delta SkyMiles Platinum card. The annual fee is quickly recouped by the card's travel perks, such as an application credit to Global Entry or TSA Precheck, annual companion certificate and so much more. Plus you can fast-track to elite status simply through card spend.Pros
- Earn bonus Medallion® Qualification Miles (MQMs) and an Medallion Qualifying Dollar (MQD) waiver when you hit specific spending thresholds with your card within a calendar year
- Receive a Domestic Main Cabin round-trip companion certificate each year
- Statement credit for TSA PreCheck/Global Entry fee (up to $100)
- First checked bag free
Cons
- Doesn't make sense if you don't fly Delta
- SkyMiles aren't the most valuable airline currency
- Earn 90,000 bonus miles after you spend $4,000 in purchases on your new Card in your first 6 months.
- Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. Payment of the government imposed taxes and fees of no more than $80 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
- Enjoy your first checked bag free on Delta flights. Plus enjoy Main Cabin 1 Priority Boarding and settle into your seat sooner.
- New: Card Members get 15% off when using miles to book Award Travel on Delta flights through delta.com and the Fly Delta app. Discount not applicable to partner-operated flights or to taxes and fees.
- Earn 3X Miles on Delta purchases and purchases made directly with hotels.
- Earn 2X Miles at restaurants worldwide including takeout and delivery in the U.S., and at U.S. supermarkets.
- Earn 1X Mile on all other eligible purchases.
- Enjoy a per-visit rate of $50 per person for Card Members and up to two guests to enter the Delta Sky Club when traveling on a Delta flight.
- Fee Credit for Global Entry or TSA PreCheck® after you apply through any Authorized Enrollment Provider. If approved for Global Entry, at no additional charge, you will receive access to TSA PreCheck.
- Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs up to two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
- No Foreign Transaction Fees.
- $250 Annual Fee.
- Terms Apply.
- See Rates & Fees