Where Do the $29 Southwest Flights Actually Go? Real Routes and How to Book Them

You’ve seen the ads: $29 one-way flights on Southwest. Your first thought? Southwest $29 flights are a scam. Or a glitch. Or maybe they only exist in Alaska in February. But they’re real-and they’re not as rare as you think. These fares aren’t magic. They’re strategic. And if you know where and when to look, you can fly across the U.S. for less than your morning coffee.

These $29 fares aren’t random

Southwest doesn’t drop $29 fares just to be nice. They use dynamic pricing to fill seats that would otherwise fly empty. These deals pop up on low-demand routes, usually midweek, and often between cities that aren’t major hubs. You won’t find them on Friday nights from New York to Los Angeles. But you might find them on a Tuesday from Nashville to Louisville, or from Orlando to Indianapolis.

Southwest’s pricing model is built around demand, not fixed routes. They have no assigned seating, no change fees, and two free checked bags. That means they can afford to undercut competitors on certain routes because they make money on extras-like EarlyBird Check-in, Wi-Fi, and Wanna Get Away+ upgrades. The $29 fare? That’s the base. The profit comes from what people add on top.

Where do these $29 flights actually fly?

Based on data from the past 12 months, the most common $29 routes are:

• Las Vegas to Phoenix
• Chicago (MDW) to Indianapolis
• Denver to Oklahoma City
• Orlando to Nashville
• San Antonio to Austin
• Atlanta to Raleigh-Durham
• Minneapolis to St. Louis
• Portland (OR) to Boise

Notice a pattern? These are all mid-sized cities with decent airport traffic but low competition. Southwest dominates many of these routes. There’s no Amtrak service. No other airlines fly direct. So Southwest sets low fares to attract price-sensitive travelers-and they usually fill those flights.

Some routes are seasonal. For example, $29 flights from Chicago to Myrtle Beach pop up in late January and early February. That’s when snowbirds are still at home and tourists haven’t started booking. Same goes for flights from Dallas to Little Rock in March-right after winter break and before spring break.

When do these deals appear?

Timing matters more than anything. Southwest releases fares 11 months in advance. That means if you’re looking for a flight in June 2026, the fares drop in July 2025. But the $29 fares? They usually appear 6 to 8 weeks before departure. That’s when Southwest starts seeing low bookings and drops prices to fill seats.

Best days to check: Tuesday and Wednesday mornings, around 10 a.m. Eastern Time. That’s when Southwest updates its inventory. Avoid weekends-those are when demand spikes and prices climb. Also, avoid holidays. You won’t find $29 fares on Memorial Day weekend or Christmas Eve. But you might find them the week after.

One real example: On January 3, 2026, a $29 fare appeared from St. Louis to Kansas City for travel on January 14. It was a 1 p.m. flight. By 4 p.m., it was gone. By the next day, the same route was $129. That’s how fast these deals disappear.

How to catch them before they’re gone

You can’t just wait for an email. Southwest doesn’t send out deal alerts like other airlines. You have to hunt. Here’s how:

1. Go to southwest.com and use the ‘Low Fare Calendar.’
2. Enter your departure city and pick a destination you’re flexible about.
3. Look for the green $29 or $39 tags on the calendar.
4. Set up a free fare alert on Google Flights or Hopper-these tools track Southwest routes and notify you when prices drop.
5. Check the app daily. The mobile app often shows deals before the website does.

Pro tip: Use the ‘Everywhere’ search. Type in your city, then click ‘Everywhere.’ You’ll see all possible destinations with the lowest fares. That’s how people find $29 flights to places they never considered-like flying from Cleveland to Grand Rapids just to get out of town for a long weekend.

What’s not included (and what you might need to pay for)

Yes, the ticket is $29. But that’s it. No seat selection. No priority boarding. No checked bags included. You get one personal item and one carry-on. If you want to check a bag, that’s $35 each way. If you want to pick a seat, you need EarlyBird Check-in ($15-$25), which automatically boards you in Group A. Without it, you’re in Group C or D-and you’ll be boarding last.

Here’s the math: A $29 ticket + $35 checked bag + $20 EarlyBird = $84. Still cheaper than most airlines’ base fares. But if you’re traveling light, you can truly fly for under $50 round-trip.

Who benefits most from these fares?

These deals are perfect for:

• Weekend warriors-people who can leave on a Tuesday and come back on a Thursday.
• Students-Southwest lets you change flights for free, so if your exam gets canceled, you don’t lose money.
• Seniors on fixed incomes-many use these fares to visit family without draining savings.
• Remote workers-fly to a new city for a week and work from a hotel.

They’re not ideal for families with strollers and 3 suitcases. And they’re not for people who need to fly on Saturday at 7 p.m. But if you’re flexible, patient, and willing to plan ahead, these fares are one of the best kept secrets in U.S. travel.

Why Southwest can do this when others can’t

Most airlines use a hub-and-spoke model. They funnel passengers through big airports and charge premium prices for connections. Southwest uses a point-to-point system. They fly directly between cities, skipping hubs. That means fewer delays, fewer connections, and lower operating costs.

They also don’t charge for change fees. That lets them overbook flights more aggressively. If someone cancels, they can instantly drop the fare to fill the seat. No waiting. No bureaucracy. Just real-time pricing.

And they don’t have elite status tiers. No first-class cabins. No premium lounges. That keeps overhead low. Their profit comes from volume, not luxury.

What to do when the $29 fare is gone

Don’t panic. Southwest’s average fare is still $150-$200 round-trip-way below the industry average. Even if you miss the $29 deal, you’re still saving hundreds compared to American, Delta, or United.

Try these alternatives:

• Book a flight 2-3 days earlier or later.
• Try a nearby airport. Flying from Houston Hobby instead of George Bush Intercontinental might save you $50.
• Use Southwest’s ‘Wanna Get Away’ fare-it’s the cheapest tier and still includes two free bags.

And remember: these fares come back. The same route that had a $29 fare in January might have another in March. Keep checking. Set alerts. Be ready.

Final thought: It’s not about the price-it’s about the freedom

The real value of a $29 Southwest flight isn’t the dollar amount. It’s the option it gives you. The ability to say ‘yes’ to a last-minute trip. To visit a friend on a whim. To take a weekend break without guilt. That’s what makes these fares worth the hunt.

You don’t need to fly every week. You just need to be ready when the chance shows up.