Image Credits: Ingfbruno, Creative Commons 3.0
Published July 30, 2024 by

Nonstop Flights: Chicago to/from Boston, Detroit, Nashville, New York, Philadelphia, Pittsburgh, Dallas, or Houston $82-$138 r/t [August-November] (No Thanksgiving) – Southwest

[07/29/2024 @ 08:47 PM CT] Deal time-stamp.
[2024-08-02 02:54:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

Deals are usually valid 24 to 72 hours after posting, but can expire at any time (see time-stamp).

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Southwest has round-trip flights from Chicago (MDW) to Boston, Detroit, Nashville, New York, Philadelphia, Pittsburgh, Dallas, or Houston (BOS, DTW, BNA, LGA, PHL, PIT, DAL, HOU) for $82-$138, NONSTOP. Flights August to November. Very few weekends available. Origin/Destination reversible. No Thanksgiving dates.

Use a card like the Southwest Rapid Rewards® Plus Credit Card to earn points towards a Companion Pass®. Companion Pass is the benefit that allows you to choose one person to fly with you, free of airline charges* every time you purchase or redeem points for a flight. *Companion Pass doesn’t cover taxes and fees.

It is common to find Southwest gift-cards for sale at a discount of about -$70 to -$20 off the redeemable value at Costco and Sam’s Club. Before you finalize your booking you should check to see if you can save more money by using a gift card.

You can usually save more money by booking your flight+hotel together as a package instead of separately.

We post new flight deals often! You can check out our other deals by returning to the Front Page of our website: escape.flights (linked).

Here are some other offers that we think are worth mentioning. List updated 04/21/2026.

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Use the example date links on our website to pull up the fare.

  • Chicago to Boston – Weekend Dates: (Southwest) Sep 06 – Sep 09 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to Detroit – Example Dates: (Southwest) Aug 28 – Sep 04 / Aug 31 – Sep 04 / Aug 31 – Sep 05 / Aug 31 – Sep 06 / Aug 31 – Sep 07 / Sep 04 – Sep 06 / Sep 04 – Sep 07 / Sep 04 – Sep 10 / Sep 04 – Sep 11 / Oct 29 – Nov 05 / Oct 30 – Nov 05 / Oct 30 – Nov 06 / Oct 31 – Nov 02 / Oct 31 – Nov 04 / Oct 31 – Nov 05 / Oct 31 – Nov 06 / Nov 02 – Nov 04 / Nov 02 – Nov 05 / Nov 02 – Nov 06 / Nov 04 – Nov 06 / Nov 05 – Nov 12 / Nov 06 – Nov 12 / Nov 06 – Nov 13 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to Detroit – Extended Weekend Dates: (Southwest) Oct 31 – Nov 04 / Oct 31 – Nov 05 / Nov 02 – Nov 04 / Nov 02 – Nov 05 / Other dates: There are more dates available than the ones we list here, experiment on your own.
  • Chicago to Nashville – Example Dates: (Southwest) Aug 28 – Sep 04 / Aug 29 – Sep 04 / Sep 01 – Sep 03 / Sep 01 – Sep 04 / Sep 01 – Sep 05 / Sep 03 – Sep 05 / Sep 04 – Sep 10 / Sep 04 – Sep 11 / Sep 05 – Sep 10 / Sep 05 – Sep 11 / Sep 06 – Sep 10 / Sep 06 – Sep 11 / Sep 07 – Sep 10 / Sep 07 – Sep 11 / Oct 29 – Nov 01 / Oct 29 – Nov 02 / Oct 30 – Nov 01 / Oct 30 – Nov 02 / Oct 30 – Nov 06 / Nov 02 – Nov 06 / Nov 02 – Nov 09 / Nov 03 – Nov 06 / Nov 03 – Nov 09 / Nov 04 – Nov 06 / Nov 04 – Nov 09 / Nov 05 – Nov 07 / Nov 05 – Nov 09 / Nov 05 – Nov 11 / Nov 05 – Nov 12 / Nov 06 – Nov 09 / Nov 06 – Nov 11 / Nov 06 – Nov 12 / Nov 06 – Nov 13 / Nov 09 – Nov 12 / Nov 09 – Nov 13 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to Nashville – Extended Weekend Dates: (Southwest) Sep 05 – Sep 10 / Sep 06 – Sep 10 / Sep 06 – Sep 11 / Sep 07 – Sep 10 / Nov 09 – Nov 12 / Other dates: There are more dates available than the ones we list here, experiment on your own.
  • Chicago to New York – Example Dates: (Southwest) Aug 13 – Aug 20 / Aug 14 – Aug 20 / Aug 14 – Aug 21 / Aug 19 – Aug 21 / Aug 20 – Aug 22 / Aug 20 – Aug 26 / Aug 20 – Aug 27 / Aug 21 – Aug 26 / Aug 21 – Aug 27 / Aug 21 – Aug 28 / Aug 22 – Aug 26 / Aug 22 – Aug 27 / Aug 22 – Aug 28 / Aug 22 – Aug 29 / Aug 26 – Aug 28 / Aug 26 – Aug 29 / Aug 26 – Aug 31 / Aug 26 – Sep 01 / Aug 27 – Aug 29 / Aug 27 – Aug 31 / Aug 27 – Sep 01 / Aug 27 – Sep 03 / Aug 28 – Aug 31 / Aug 28 – Sep 01 / Aug 28 – Sep 03 / Aug 28 – Sep 04 / Sep 04 – Sep 06 / Sep 04 – Sep 09 / Sep 04 – Sep 10 / Sep 04 – Sep 11 / Sep 05 – Sep 09 / Sep 05 – Sep 10 / Sep 05 – Sep 11 / Sep 05 – Sep 12 / Sep 06 – Sep 09 / Sep 06 – Sep 10 / Sep 06 – Sep 11 / Sep 06 – Sep 12 / Sep 07 – Sep 09 / Sep 07 – Sep 10 / Sep 07 – Sep 11 / Sep 07 – Sep 12 / Sep 07 – Sep 14 / Sep 09 – Sep 11 / Sep 09 – Sep 12 / Sep 09 – Sep 14 / Sep 09 – Sep 16 / Sep 10 – Sep 12 / Sep 10 – Sep 14 / Sep 10 – Sep 16 / Sep 10 – Sep 17 / Sep 11 – Sep 14 / Sep 11 – Sep 16 / Sep 11 – Sep 17 / Sep 11 – Sep 18 / Sep 14 – Sep 16 / Sep 14 – Sep 17 / Sep 14 – Sep 18 / Sep 14 – Sep 19 / Sep 14 – Sep 21 / Sep 16 – Sep 18 / Sep 16 – Sep 19 / Sep 16 – Sep 21 / Sep 16 – Sep 23 / Sep 17 – Sep 19 / Sep 17 – Sep 21 / Sep 17 – Sep 23 / Sep 17 – Sep 24 / Sep 18 – Sep 21 / Sep 18 – Sep 23 / Sep 18 – Sep 24 / Sep 18 – Sep 25 / Sep 19 – Sep 21 / Sep 19 – Sep 23 / Sep 19 – Sep 24 / Sep 19 – Sep 25 / Sep 23 – Sep 25 / Sep 24 – Oct 01 / Sep 25 – Oct 01 / Sep 25 – Oct 02 / Oct 29 – Nov 05 / Oct 30 – Nov 05 / Oct 30 – Nov 06 / Oct 31 – Nov 05 / Oct 31 – Nov 06 / Nov 02 – Nov 05 / Nov 02 – Nov 06 / Nov 03 – Nov 05 / Nov 03 – Nov 06 / Nov 04 – Nov 06 / Nov 05 – Nov 09 / Nov 05 – Nov 12 / Nov 06 – Nov 09 / Nov 06 – Nov 12 / Nov 06 – Nov 13 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to New York – Weekend Dates: (Southwest) Sep 06 – Sep 09 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to New York – Extended Weekend Dates: (Southwest) Aug 22 – Aug 26 / Aug 22 – Aug 27 / Sep 05 – Sep 09 / Sep 05 – Sep 10 / Sep 06 – Sep 10 / Sep 06 – Sep 11 / Sep 07 – Sep 09 / Sep 07 – Sep 10 / Sep 14 – Sep 16 / Sep 14 – Sep 17 / Sep 19 – Sep 23 / Sep 19 – Sep 24 / Oct 31 – Nov 05 / Nov 02 – Nov 05 / Other dates: There are more dates available than the ones we list here, experiment on your own.
  • Chicago to Philadelphia – Example Dates: (Southwest) Aug 28 – Sep 04 / Aug 31 – Sep 04 / Sep 04 – Sep 06 / Sep 04 – Sep 07 / Sep 04 – Sep 10 / Sep 04 – Sep 11 / Sep 05 – Sep 07 / Nov 01 – Nov 04 / Nov 01 – Nov 05 / Nov 03 – Nov 05 / Nov 03 – Nov 09 / Nov 04 – Nov 09 / Nov 05 – Nov 09 / Nov 05 – Nov 12 / Nov 06 – Nov 09 / Nov 06 – Nov 12 / Nov 06 – Nov 13 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to Philadelphia – Weekend Dates: (Southwest) Nov 01 – Nov 04 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to Philadelphia – Extended Weekend Dates: (Southwest) Nov 01 – Nov 05 / Other dates: There are more dates available than the ones we list here, experiment on your own.
  • Chicago to Pittsburgh – Example Dates: (Southwest) Sep 01 – Sep 04 / Sep 01 – Sep 05 / Sep 01 – Sep 06 / Sep 01 – Sep 07 / Sep 04 – Sep 06 / Sep 04 – Sep 07 / Sep 04 – Sep 08 / Sep 05 – Sep 07 / Nov 01 – Nov 03 / Nov 01 – Nov 04 / Nov 01 – Nov 05 / Nov 01 – Nov 06 / Nov 02 – Nov 04 / Nov 02 – Nov 05 / Nov 02 – Nov 06 / Nov 02 – Nov 09 / Nov 03 – Nov 05 / Nov 03 – Nov 06 / Nov 03 – Nov 09 / Nov 04 – Nov 06 / Nov 04 – Nov 09 / Nov 05 – Nov 09 / Nov 06 – Nov 09 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to Pittsburgh – Weekend Dates: (Southwest) Nov 01 – Nov 03 / Nov 01 – Nov 04 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to Pittsburgh – Extended Weekend Dates: (Southwest) Nov 01 – Nov 05 / Nov 01 – Nov 06 / Nov 02 – Nov 04 / Nov 02 – Nov 05 / Other dates: There are more dates available than the ones we list here, experiment on your own.
  • Chicago to Dallas – Example Dates: (Southwest) Aug 28 – Sep 04 / Aug 31 – Sep 04 / Sep 04 – Sep 06 / Sep 04 – Sep 07 / Sep 04 – Sep 10 / Sep 04 – Sep 11 / Sep 05 – Sep 07 / Oct 29 – Nov 05 / Oct 30 – Nov 05 / Oct 30 – Nov 06 / Nov 01 – Nov 03 / Nov 01 – Nov 04 / Nov 01 – Nov 05 / Nov 01 – Nov 06 / Nov 02 – Nov 04 / Nov 02 – Nov 05 / Nov 02 – Nov 06 / Nov 02 – Nov 09 / Nov 03 – Nov 05 / Nov 03 – Nov 06 / Nov 04 – Nov 06 / Nov 04 – Nov 09 / Nov 05 – Nov 09 / Nov 05 – Nov 12 / Nov 06 – Nov 09 / Nov 06 – Nov 12 / Nov 06 – Nov 13 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to Dallas – Weekend Dates: (Southwest) Nov 01 – Nov 03 / Nov 01 – Nov 04 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to Dallas – Extended Weekend Dates: (Southwest) Nov 01 – Nov 05 / Nov 01 – Nov 06 / Nov 02 – Nov 04 / Nov 02 – Nov 05 / Other dates: There are more dates available than the ones we list here, experiment on your own.
  • Chicago to Houston – Example Dates: (Southwest) Aug 28 – Sep 04 / Sep 04 – Sep 06 / Sep 04 – Sep 10 / Sep 04 – Sep 11 / Sep 05 – Sep 10 / Sep 05 – Sep 11 / Sep 06 – Sep 10 / Sep 06 – Sep 11 / Sep 07 – Sep 10 / Sep 07 – Sep 11 / Sep 07 – Sep 14 / Nov 01 – Nov 03 / Nov 01 – Nov 05 / Nov 01 – Nov 06 / Nov 02 – Nov 05 / Nov 02 – Nov 06 / Nov 04 – Nov 06 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to Houston – Weekend Dates: (Southwest) Nov 01 – Nov 03 / Other dates: There may be more dates available than the ones we list here, experiment on your own.
  • Chicago to Houston – Extended Weekend Dates: (Southwest) Sep 05 – Sep 10 / Sep 06 – Sep 10 / Sep 06 – Sep 11 / Sep 07 – Sep 10 / Nov 01 – Nov 05 / Nov 01 – Nov 06 / Nov 02 – Nov 05 / Other dates: There are more dates available than the ones we list here, experiment on your own.

I was able to pull this up on Southwest Airlines.

When you are ready to book your flight or hotel, please use the links on our site to begin your booking process so we receive credit for the referral.

  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on Expedia, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.


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Ren P. Artemio

Ren P. Artemio

Ren is the Chief Director of Nap Times at Escape Houston, Escape ATX, Cheap DFW, and Escape Flights. He really likes researching airfare and the travel industry, especially when it means getting a cheap flight to anywhere (he's not picky).

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