Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
Published October 16, 2024 by

Cheap Flights: Denver or Chicago to/from Atlanta, Austin, Detroit, Los Angeles, Minneapolis, Phoenix, Portland, Seattle, Salt Lake, Boston + more (see full list on website) $84-$132 r/t [Nov-Dec] – Southwest

This list was updated and refreshed on October 16, 2024 @ 02:54 PM Central Time.

This post will be updated throughout the day, each day, until the prices increase back above their moving averages. Refresh this page in your browser.

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

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To book: Use our updated link list. Chicago, Denver
Or book with these sites: Southwest, Expedia, Priceline, BookingBuddy, Travelocity, Tripadvisor, Skyscanner, Orbitz, Hotwire, CheapTickets, Kayak.

Southwest has round-trip flights from Denver or Chicago (DEN, MDW) to Various destinations in the United States for $84-$132, NONSTOP or with a connection. Flights November to December. Very few weekends available. Origin/Destination reversible. No Christmas dates available.

When these type of “wide” sales happen, they are often matched by other airlines eventually.

If you like this style of report, it’s a subset of daily Patreon recap [link]. That recap is the unfiltered list of every fare that was priced below the 6-month moving average.

Here are some other offers that we think are worth mentioning. List updated 12/04/2025.

We now track coupon codes, discount codes, gift card discounts, and credit card offers that have a better value than their historical averages.


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

This list was updated and refreshed on October 16, 2024 @ 02:54 PM Central Time.

Nonstop: Flights from Denver

Nonstop: Flights from Chicago and Milwaukee

With-Stops: Flights from Chicago and Milwaukee

Southwest Airlines Flights from Chicago and Milwaukee

I was able to pull this up on Google Flights and Expedia.

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: The Chase Sapphire Preferred® Card allows for 1-to-1 point transfers to several airline loyalty programs. Booking with points is a good alternative to paying with cash when the price of airfare is high. Here is the current list of Chase Sapphire transfer partners: United, Southwest, jetBlue, British Airways, Iberia, Singapore Airlines, Emirates, Air France, KLM, Virgin Atlantic, Aer Lingus, and Air Canada.
  • Tips: Use Tripadvisor to create a Hotel “short list”. First, plug in your dates and destination. Then select “Sort by Traveler Ranked”. Finally, select the “Traveler Ranking” filter to show “only 4* and up”. Use this resulting “short list” of hotels to find the cheapest one with a high ranking.
  • Tips: Hotel rates for Weekend dates are usually higher than the rates for Sunday through Thursday. Tripadvisor has a color-coded date calendar, red when the average hotel price for that day is more expensive, green for less expensive. You can use this to get an overview of what dates in the month are at a discount.
  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on BookingBuddy, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.


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Flights departing from a different city:

Other Useful Links:

  • [Budget Travel] – list all the posts that deal with Budget Travel (filter out all the flight deal posts)

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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