You’re standing at Midway, not O'Hare. That’s the first thing you have to wrap your head around when booking Chicago to Las Vegas Southwest flights. If you show up at ORD looking for that heart-shaped logo, you’re going to have a very bad, very expensive morning. Southwest basically owns Midway (MDW), and for those of us living on the South Side or in the South Suburbs, it’s a godsend. But even for North Siders, the trek down the Orange Line is usually worth it because Southwest does things differently than the legacy carriers.
It’s about the bags. Two of them. Free.
Honestly, in an era where United and American will charge you for the air you breathe if they could find a way to meter it, Southwest’s "Bags Fly Free" policy is still the heavyweight champion of the route. When you're heading to Vegas, you’re probably bringing more than a swimsuit. You’ve got the nice shoes for the steakhouse, the "maybe" outfit for the club, and probably an extra empty suitcase for the stuff you’ll buy at the North Premium Outlets.
The Midway Advantage and the Terminal Reality
Midway is small. Compared to the sprawling, soul-crushing labyrinth of O’Hare, MDW feels like a neighborhood airport. You can get from the security line to your gate in fifteen minutes on a good day. Southwest dominates the concourses here. If you’re flying Chicago to Las Vegas Southwest, you’re almost certainly departing from Concourse A or B.
But don't get it twisted—Midway has its quirks. The security line can look terrifyingly long, snaking back toward the parking garage bridge, but it moves. Usually. The food options are actually decent now, too. Most people gravitate toward the central food triangle, but if you want to avoid the crowds, keep walking toward the gates. There's a Billy Goat Tavern if you need a "cheezborger" before you hit the desert, though honestly, Harry Caray’s Shortstop is better for a quick sandwich.
The flight itself is about three and a half to four hours. Coming back? It’s faster because of the tailwinds. Going out, you’re fighting the jet stream. You’ll cross over the Rockies, and if you’re sitting on the right side of the plane (the "starboard" side for the sailors among us), you might catch a glimpse of the Grand Canyon if the pilot takes a southerly route.
Cracking the Southwest Boarding Code
There are no assigned seats. This stresses people out. I’ve seen grown adults nearly come to blows over the "A-List" boarding sequence.
If you want a good seat on your Chicago to Las Vegas Southwest leg, you have to check in exactly 24 hours before departure. Not 23 hours and 59 minutes. Exactly 24 hours. If you wait until 20 minutes after the window opens, you’re stuck in the "C" group. That means you’re sitting in the middle seat between a guy who didn't shower and someone who brought a tuna sandwich on board.
Is EarlyBird Check-In worth it?
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It depends. If you’re flying on a Friday afternoon when every bachelor party in Cook County is heading to Nevada, then yes. Pay the $15 to $25. It checks you in automatically before the general public. If you’re flying on a random Tuesday morning, you can probably skip it.
What about the "LUV" Vibe?
Southwest flight attendants are... a choice. Sometimes you get the legendary comedian who does the safety briefing as a stand-up routine. Other times, you get someone who just wants to get the pretzels handed out so they can sit down. It’s inconsistent, but it’s rarely cold.
The WiFi is $8. It’s fine for iMessage or scrolling Twitter (I refuse to call it X), but don't try to stream Netflix. Download your shows before you leave the house. Also, Southwest doesn’t have seatback screens. You use your own device to access their portal for free movies and live TV. If you forget your iPad, you’re staring at the back of a headrest for 1,700 miles.
Timing the Market: When to Book
Vegas is a weekend town. Everyone wants to leave Chicago on Thursday or Friday and come back Sunday or Monday. Because of that, Southwest’s "Wanna Get Away" fares fluctuate wildly.
I’ve seen flights for $99 one way, and I’ve seen them for $450.
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- Tuesday and Wednesday: These are the cheapest days to fly. Period. If you can swing a mid-week trip, you’ll save enough for an extra night at the Wynn.
- The 21-Day Rule: Generally, Southwest’s lowest tiers disappear three weeks out.
- The Sale Cycles: Southwest runs these "WOW" sales and "40% off" promos every few months. Sign up for the emails. They’re annoying until they save you $200.
One thing people forget is that Southwest doesn't show up on Google Flights or Expedia. You have to go to their website. It’s a pain in the butt for price comparison, but it’s how they keep their costs (and your fares) lower.
Navigating Harry Reid International (LAS)
When you land in Vegas, you’re arriving at Harry Reid International. Southwest uses Terminal 1.
Here is the most important piece of advice I can give you: Do not take the first taxi you see. The ride-share lot (Uber/Lyft) is in the parking garage. It’s a bit of a hike, but it’s usually cheaper and you won't get "long-tunneled." That’s a scam where cabbies take the tunnel to the Strip, adding ten bucks to your fare. Just tell them "no tunnel" if you take a cab.
The slot machines in the airport have the worst odds in the city. They’re there to catch the desperate and the tourists who don't know any better. Wait until you get to the hotel.
Southwest vs. The Rest: Is It Actually Better?
Look, United flies from O’Hare to Vegas. Spirit and Frontier fly from both. Why choose Chicago to Las Vegas Southwest?
It’s the flexibility.
Southwest doesn’t have change fees. If your boss cancels your vacation or you realize you’re too broke to go to Vegas, you can cancel your flight and get a credit that doesn’t expire. No other airline is that chill about it. Also, the lack of "Basic Economy" nonsense means you aren't treated like a second-class citizen just because you wanted a cheap ticket. You get a full-sized carry-on and a personal item regardless of what you paid.
However, the boarding process is a literal cattle call. If you have mobility issues or you're traveling with a huge family, it can be chaotic. Families with kids under six get to board between groups A and B, which is a massive perk. If you're a solo traveler, you're at the mercy of the "A" group's speed.
The Chicago Winter Factor
We have to talk about snow. Midway is a "tight" airport. When a blizzard hits Chicago, MDW often shuts down or sees massive delays faster than O'Hare because O'Hare has more runways and more equipment. If you’re booking a trip in January, keep an eye on the "Wanna Get Away 8" (the new fare class) options that allow for easier rebooking.
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Southwest is pretty good about issuing "Travel Advisories" that let you change your flight for free if a storm is coming. Take advantage of that. Don't wait until you're stuck at the gate eating a soggy pretzel while watching the de-icing trucks fail.
Making the Most of the Route
- Check-In via App: Don't use a mobile browser. The app is faster.
- Drink Coupons: If you have the Southwest Rapid Rewards credit card, you occasionally get drink coupons in the mail. Use them. A Gin & Tonic on a 4-hour flight makes the time fly.
- The "L" Train: The Orange Line is $2.50. An Uber from the Loop to Midway is $40-$60. If you don't have a ton of luggage, take the train. It ends literally inside the airport.
- Boarding Position 1-15: You can often "upgrade" your boarding position at the gate for about $30-$50 if it's available. If you absolutely need an exit row for the legroom, this is the way to do it.
The Reality of the "Southwest Effect"
There’s a reason this specific route is so popular. It’s the bridge between the Midwest work ethic and the desert's total lack of ethics. You’ll see people in suits heading for a convention at Mandalay Bay sitting next to a group of girls in matching "Vegas Before Vows" t-shirts.
Southwest makes the trip accessible. It’s the "people’s airline" for a reason. You aren't getting a first-class cabin because there isn't one. Everyone is in the same boat—or plane. Whether you’re a high roller or a penny slot enthusiast, you’re all getting the same bag of snack mix.
Final Actionable Steps
- Audit your luggage: Since you get two free bags, don't cram everything into a carry-on. Check the heavy stuff and walk through the airport with just a small backpack. Your shoulders will thank you.
- Set a "T-24" Alarm: Set a phone alarm for exactly 24 hours and 2 minutes before your flight. Be ready.
- Download the Entertainment: The Southwest app/portal is your only source of fun. Make sure your phone is charged; Midway has plenty of outlets, but the older Southwest planes don't have USB ports in every seat yet.
- Check the "Low Fare Calendar": If your dates are flexible, use the calendar tool on the Southwest site. It's the only way to find those elusive $79 fares.
- Join Rapid Rewards: Even if you only fly once a year, the points don't expire. It’s free money.
Stop overthinking it. Book the flight, grab a window seat if you get an "A" boarding pass, and get ready for the heat. Vegas is waiting, and Midway is the easiest way to get there from the 312 or the 773. Just remember: stay hydrated, keep your boarding pass handy, and for the love of everything, don't be the person who tries to board with the "A" group when you have a "C" ticket. They will send you back to the end of the line, and the whole plane will judge you.