[07/21/2016 @ 1:20 PM] Book this fare on: Southwest, (Other Airlines: BookingBuddy, Hotwire, Priceline, Travelocity, Expedia, Orbitz).
[07/29/2016 @ 12:00 PM] Most UA fares gone.
[08/30/2016 @ 12:08 PM] Southwest still available.
[12/09/2016 @ 12:33 PM] Old post clean-up. Removing from deal list.
The details on this page were accurate when this post was last updated (see time-stamps above). Prices and availability can and will change, given enough time. This page contains links to companies that may compensate this site when you click on their link and purchase travel from their website.
Southwest Airlines has round-trip flights from Houston (HOU) to Chicago (MDW) for $88, NONSTOP. $44 each-way. Flights NOV-DEC. No Holidays. Fare is reversible.
Note: There are a lot of $44 departures, but no $44 returns in September and October.
- Example Dates: (Southwest) Nov 02 – Nov 06 / Nov 17 – Nov 20 / Dec 09 – Dec 11 / Other dates: Use the Fare Calendar at Southwest.
Example Dates: UNITED (Priceline / Travelocity) Sep 17 – Sep 20 / Sep 21 – Sep 28 / Sep 07 – Sep 14 / Sep 13 – Sep 21 / Oct 18 – Oct 25 / Other dates: Try TUE/WED/SAT flights in September.
- Before you finalize your purchase, use BookingBuddy to see if any other airline is offering a better deal. United will often match sales for this route.
- If you want to see other deals that are still bookable you should check out the “Bookable Deals” page on our site. It filters out deals that have expired, or have low availability.
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.
Fare availability screenshots were taken at 12:07 PM on 08/30/16.
I was able to pull this fare up on Southwest. Screenshot taken at 12:14 PM on 08/30/16.
If you plan on booking a hotel, use our travel coupon codes to save up to 15% to 20% off. Alternatively, you may be able to save the most money by booking your trip as a Flight + Hotel package on Southwest Vacations, Priceline, Orbitz, or Travelocity.
To find this fare on Southwest Airlines, you should be using the Fare Calendar on their site. If you’re just plugging in random dates and hoping to land a fare, you’re doing it wrong. More details on the Fare Calendar are covered in this post: [Use the Fare Calendar to find the cheapest flights on Southwest Airlines].
Southwest never charges a change or cancellation fee. If you cancel within 24-hours they will reverse the credit card charge. If you cancel before your flight, they will give you a travel voucher that you can apply for future travel valued at the full price you paid. Voucher isn’t transferable and expires after 1-year, but it beats getting hit with a change fee.
Flight Details:
- Full Route: HOU-MDW-HOU
- Previous Lowest Price Average: $136
- Book this fare on: Southwest, (Other Airlines: BookingBuddy, Skyscanner, Priceline, Travelocity, Expedia, Orbitz)
Destination information:
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