Southwest and MDW go together like Southwest and Love Field. It's a super hub for the airline and they handle the traffic well. The gate areas are super congested and crowded and poorly designed for seating. It definitely isn't the best. The staff is awesome and gets the masses on the plane in an organized way! The staff always make is bearable though. read more

Southwest Airlines - Traveling with friends makes time fly... literally - Airlines Near Me - Chicago, Illinois

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I used to love SWA. I literally chose my place to live based on being on a SOUTHWEST hub. Well, they are different now. Moreso this Midway location than all others. They are not the happy fun place circa 1995 to COVID. THEY ARE RUDE like United O'HARE. They are unevenly enforcing carryon baggage count. I've watched CLT say put smaller fanny packs into 1 of your carry-ons and thought ohhh....they are serious like Ryan Air in Europe Today, 9/9/26 - 1 man have 4 bags. 2 luggage carry-ons+ 1 shopping bag and a briefcase in addition to his 2 rolling carry-ons. I figured be may be a cc carrier or exempt yet boarded Group 5. Elder couple had to be split up because wife was group 5 but he was group 8. They genuinely made him wait. Wifey got her rolling little carry-on not a 20in nor 18in and the gate agent immediately questioned her luggage count. Y'all she had a shopping bag from the concourse and that's it. I flew out from MDW on 8.13.2026 for the first time in forever. Had a bigoted encounter 8.12.2026 with Stephanie in the baggage check-in area. Now, today and 8/12th was enough for me but mannnnn our outbound 9.2.26 flight was delayed that we arrived Midnight central time which was well after our 735p scheduled time. They sent $100 Luv vouchers which I'm learning today can only be applied for flights whereas I'm thinking they can be spent at SWA so let me pay for luggage. Nope! In all. It's just too much. One would expect all the rigor from Frontier Airlines or any other budger carrier y'all prefer to mock but with Candor ... I haven't had such from Frontier and I don't these shenanigans from Southwest. read more

Southwest Airlines - Arrived 5 hours later and still waiting for luggage that I wish we never checked - Airlines Near Me - Chicago, Illinois

Southwest through Midway has been a breeze! The place is easy to maneuver - the terminals are large and spacious with plenty of room at gates and concourses and restaurants/stores. The choices and selections are high quality and vary with appropriate variety for large and diverse groups of people moving to and fro headed wherever they may go! read more

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Not one of my greatest experiences with SWA.. Flight MDW to MCI and flight attendants Chavez & Angelette were very abrupt in rude with questions I had, providing service or rather not providing service. It took on sixth pass for Angelette to grab my trash vs other passengers. I had to say Excuse me and raise my discarded items she proceeded to get the passenger in front of me, dropping their plastic water bottle; then grabbing my cup and proceeded to give me instructions to put my purse under the seat. So glad I made it home. read more

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I still enjoy fly Southwest every now and again depending on where I'm going. I am highly bummed out that they now charge to check bags and assigned seating. Southwest is like the other airlines now. I've also noticed the customer service whether over the phone or in person has gone downhill drastically. It's unfortunate Southwest took the charm it once had away. read more

Why do we have assigned seats and no free checked baggage now? The whole point of Southwest wasn't so much the prices, it was knowing exactly the alternative format and inviting offers. read more

Southwest Airlines - Waiting - Airlines Near Me - Chicago, Illinois

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Realities and perceptions change. Despite several setbacks during my birthday trip to Chicago, the Spanish-speaking team at Southwest Airlines: Linda, Nataly, and Emily; showed extraordinary dedication. They focused not only on company procedures but on the well-being of the traveler, offering support, empathy, and real solutions at every moment. Thanks to them, everything was resolved in the best possible way. Today, with gratitude and relief, we're heading back to California Thank you, Southwest Airlines Spanish Team. Your commitment and human touch truly made the difference. read more

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Has become much worse since all the changes. Most recent example I finally decided I had to leave a review. I've been unable to book a flight on the southwest website for 2 days. I keep reaching an error code. I tried clearing cookies, using a different browser, paying as a guest, all with no luck. Each of the last 2 nights I've tried to call and have been on hold for over an hour both times. I opted to get a call back yesterday and was on another line when they tried to call 2 hours later. Tonight I'm still waiting. Crazy that my complaint is that I literally can't pay this company money but it is what it is. read more

Southwest Airlines - my time on hold screenshot - Airlines Near Me - Chicago, Illinois

I absolutely love flying Southwest Airlines and this location is no exception. There's just something so easy about their terminals offering plenty of seating, food court and shopping options, charging stations, friendly, helpful staff and organized boarding processes. There's never an issue when I fly through here. read more

I've flown Southwest for decades. VERY disappointed they left ORD (O'Hare) for MDW (Midway). There is nowhere to sit. There are ATM's but all the concessions are card only; most short staffed. The airport staff isn't the friendliest around. Unfortunately I will have to find other airlines to travel with if it means being able to avoid MDW as a layover at any cost. The 3 stars is because as a while, I like Southwest read more

I flew Southwest from BWI into Chicago Midway for business this week and had an encouraging experience. First time. The nuts were crunchy... the Sprite was cold and the flight got in on time with minimal to no turbulence. Correction- it was delayed at point of origin for 1.5 hours but I wasn't trippin'. Return flight is going to be on Frontier - also first time. That should be an adventure. :/ read more

Anytime I fly into or our of Chicago, Southwest via Midway is always top of my preference list. Given the amount of directs to and from, they always come in clutch and make travel days a bit less worrisome than other carriers, at least for me. My latest travel via SW at MDW was a round trip from BNA. Incoming flight and deplaning at MDW was okay, no issues. Boarding, departure and the flight itself headed back was also solid, on time and uneventful. Gate agents for SW can be hit and miss, but they always seem helpful when needed. The gate for my departing flight changed, and I appreciated the clear and multiple announcements made in the gate area. The planes definitely could use some upgrading. Seats are comfortable and space is decent, but the entertainment and electrical ports need some help. Overall, since moving to BNA, I have become a Southwest loyalist. MDW is one of my repeat destinations each year and I appreciate SW making it happen with minor issues, if any at all, each time. read more

Horrible. The women at gate B11 , Denise and Rosie ganged up on our daughter. It was so bad it provoked an asthma attack. They should be ashamed of themselves for such unprofessional behavior. Southwest management please look into these employees .July 14, 5:30 AM flight from Midway to Austin Texas. Flight 2726. They were bullies and mean. Unacceptable, read more

Had a layover through here. Not bad of a setup though i think the back end is a little crowded as most of the flights did cone through this section. read more

It was definitely an... experience. The staff at the gate from MCO to Chicago ORD was super kind and we were running late and they let us in with no problem. The flight was super empty and we had our choice of where to sit together (2 travelers). We chose the emergency exit row and the schpeal was given to us clearly and quickly. Here's the kicker. The flight attendants were all very kind. However, we had a pretty bumpy flight and the head attendant kept having to tell people to stay buckled and in their seats. Nearing the end of the flight, over the intercom she went "Ladies and gentlemen... we are going down." proceeded to pause, and then continued "stay in your seats until we arrive at the gate." Biggest heart attack we've ever had on a plane. No "just kidding" or anything. Anyways we landed just fine. But someone needs to tell that lady to change the descending language or get a new sense of humor if that's what that was. read more

This was definitely a different airline experience for me! First time ever flying, where you don't choose your seats when purchasing tickets. I decided to pay a little extra for the early boarding and I checked in on the app as close to the 24 hour check in time as possible and was able to be in the first group boarding, which was kind of cool we were able to sit in the very front lots of big legroom there but unfortunately, the rest of the seats are all squished together and that!? I am not a fan of! The airline attendants were wonderful! The snacks? They gave us pretzels and Oreo cookies! Seriously? And for a four hour flight, they did not offer any other food options drink options were good. I think I prefer other airlines over Southwest read more

I flew to Long Beach this weekend. Upon leaving Memphis, there was a notification that bad weather was happening in the Northeastern part of the US. I have not heard of any new weather updates and I am no meteorologist, but most of the time with greater than 3-hr delays, there's some idea of how bad weather is. I had one layover on my flight to Long Beach and one back to Memphis. We left Memphis on time, and every flight after was delayed greater than an hour with no real explanation. But after researching your recent reviews, this is becoming a thing for Southwest. Delaying flights due to "weather conditions" unbeknownst to the public. Blaming the weather without storms or strong gusts of winds noted on weather apps seems a bit made up and almost like this is becoming your excuse to delay flights without compensation. I will do my absolute best not to fly with Southwest again. I had a recent experience back in June where my flight was delayed and we were aware of the storms because the employees knew. No one here in Denver is aware of any weather issues (likely because there are none)...I said all that to say pay the money for Delta!! Southwest will be a last resort for me moving forward. Update: they ended up delaying the flight until they decided to cancel it hours after we'd been waiting. I'm sure they knew it would end up being cancelled. They rebooked us for the following morning (extremely inconvenient) and offered a hotel that was booked by the time the link actually was working. And I am sure they will have no compensation will be offered to those who chose not to use the hotel because of timing. You cancel the flight at 11 PM, offer hotels 21 miles away, and expect us back within 3-4 hrs to RECHECK in?! Make it make sense. I'm so disappointed SW. read more

Southwest Airlines - The advisory alert that is presented. Not a storm. Not strong gusts of wind. - Airlines Near Me - Chicago, Illinois

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Flying Southwest out of Chicago was surprisingly painless. The staff were friendly, the boarding process didn't feel like a wrestling match, and the flight was on time. Bigger overhead bin storage was a plus! Seats aren't first-class, but hey, neither is my budget, still, I survived in comfort! read more

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This Southwest Airlines is located in Chicago Midway International Airport. When flying out to Lombard Chicago from Las Vegas, I typically fly Southwest, non-stop, to Chicago Midway. All of my flights are typically on-time or early! This latest flight coming from Las Vegas to Midway on a Sunday, arrived 30 minutes early! The Southwest Airlines terminal is beautiful in Midway! There are so many restaurants and shops available inside the terminal! The Southwest Team at Chicago Midway are amazing too! When I check my bag at their luggage or have any questions to ask at the gate, the team members are super helpful! The boarding process is relatively easy and smooth. They call up different sections to board the plane, unlike other airlines where you choose a seat prior to paying for your ticket. A drink and snacks are offered on Southwest Airlines if the flight is long distance. I'll be flying out from Chicago Midway on Friday back to Las Vegas! I don't use any other airline to fly from Vegas to Chicago! It's a great experience! read more

Southwest Airlines - Airlines Near Me - Chicago, Illinois

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i've been stuck here for 2 days, and today there isnt so much as a cloud in the sky. i've remained calm and collected, because i understand that none of this is the fault of the staff on the ground. But they could at least return the courtesy - multiple staff members have been curt and unhelpful, to the point that it's almost like they think i stranded them in a random city on what was supposed to be a 2 hour stopover, with no luggage and no attempt to make good whatsoever. I am never flying Southwest again. read more

I had a pretty bad experience on my southwest airline flights and was given a survey letting them know how bad the service was. At the end, it said we can't help you here but gave a link that said that if you have problems, you can get it resolved here. Well, I clicked on the link and this is what I got. Their service went from the best in the business to the worst. read more

Southwest Airlines - Southwest screenshot - Airlines Near Me - Chicago, Illinois

Chicago Frantic yet efficient. One of the most packed places for southwest. Lots of folks who were unfamiliar with the process. They were redirected which allowed folks to get boarded. Once boarded to achieve the on time departure we were placed on hold for maintenance. Always frustrating and a relative in common event. Kind folks took most of the edge off the frustration. The lady next to me offered me some tasty come. The kind gesture was accepted and smacking on the fresh gum helped with the delay. The flight was entirely full. Actually overbooked and a $1,200 voucher was offered up. If I was traveling alone I would have taken advantage of the offer. The boarding are was packed. It took some effort to grab a seat. Overall a pleasant experience. Still waiting to depart. Pilot just came on and assured we'd be wheels up shortly. I'll take his word an close out the review. If there are any changes be assured I'll be back to edit. More delays. One star deduction! lol So, this is one of the nicer planes. read more

Southwest Airlines - Airlines Near Me - Chicago, Illinois

When I say Southwest Airlines couldn't have given me a better start to my trip. These two truly made my bachelorette experience beyond what I could've ever imagined read more

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The incident on May 23, 2026 should have never happened. The mother struggling to board with her mental disabled children was painful to hear. Do better, Southwest Airlines. read more

Southwest Airlines is my absolute favorite airline to flying from Las Vegas to Chicago and back to Vegas. Booking directly on the Southwest Airlines app, and it's very easy! Planes are clean, seats are comfortable. Service is great, and attentive. No other airline can beat the (2) free checked bags! I also like the no seat assignment system. Hope they are keeping it! I love the free WiFi and the onboard entertainment options. Snacks and nonalcoholic beverages are also included! Alcoholic beverages can be purchased. read more

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Southwest Airlines is a great way to fly! From booking to checking and flight info, this airline is my favorite. The app is easy to use, the pre-booking and no baggage fees are the best! I will be using Southwest for all my future flights and glad to have use them on my holiday ventures. I highly recommend Southwest Thank you for your great service read more

Southwest Airlines - Airlines Near Me - Chicago, Illinois

I can't and won't say anything but great things about Southwest as I travel exclusively with them simply for the fact that they allow 2 free checked bags & 2 free carry on bags along with an open seating policy. Always friendly staff read more

Southwest Airlines - Airlines Near Me - Chicago, Illinois

I've flown Southwest for years as my choice airline. Not any longer. This last year has shown a consistent decline in services. Today was the worst. Such poor Customer service at the terminal boarding check in-outright rude and dismissive when we were being respectful and just asking questions why our connecting flight was delayed 7 hours. Stuck in a terminal with my grandkids, who are great, but worried they don't make our reservations before my grandson's travel team baseball game. Now we're in a secondary connecting flight that's going away from our final destination that will possibly get delayed or canceled. I understand weather issues. But we have family at our destination and they confirm there are NO WEATHER ISSUES! Southwest seems to just be behind and again using weather as their liability excuse. I'm finished with them. If you haven't tried them, please DON'T!! read more

This is specifically for my Southwest experience at Midway, since that's the address listed for this Yelp business entry. They cover a large part of the flights in and out. Check-in was a breeze. The staff working at each gate are professional and friendly, and they can also be a bit entertaining among their announcements and sometimes the chatter they share as they banter with each other. Airport experiences aren't always enjoyable - the folks who help you here do their part to make it better. read more

Southwest is a great discount airline. On a good day their fares are very low compared to the legacy carriers and I get free baggage check and free seat selection at boarding time. Just be quick to check in early so you can get a good position in the boarding process. They fly to a lot of places in the US and Caribbean, so it's an easy choice for a short trip. I don't know if I would take them on a very long trip since their 738 regular seats are not that great for a long long flight. I have flown them probably over 20-30 times and I have always found their flight attendants very cheerful, happy and attentive. A good choice....and if you are a member of their rewards program...you get points toward future flights.... read more

Southwest Airlines - Airlines Near Me - Chicago, Illinois

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The boarding process is terrible. And they charge extra for this experience. It took 40 minutes to board. They assign seats rather than allowing seat assignment when buying the ticket. Just a money grab. read more

Southwest is pretty good. Checking in bags can be quick, printing out paper boarding pass can be quick also if you know your confirmation number, and picking up bags can also be quick too. I like how SW has credit toward other flights in case you need to change your flights or even cancel flights! read more

I really recommend this airline. I was planing to go to Kansas then to Chicago. Then things changed and I already had tickets booked for Kansas and Chicago. Then I had to cancel the trip to Kansas because it was not fitting with the concert tickets I already bought a year ahead. I forgot. So when I remembered I decided not to go to Kansas. So it was very easy to make the changes on the southwest app. There was No extra charge for changing the tickets. Now I have one ticket to Kansas that I can use any time. My flights were on time and very easy to check in on the app. I was able to check in a big luggage without any extra cost. I will use their services again when. I have the chance. Definitely great service and helpful attendants. I didn't get any pictures of the inside of the plane. The room is very limited if you want to be spacious you have to pay for that. read more

Southwest Airlines - Ready for the long day!! HHD everyone!! Little vacay it's over. - Airlines Near Me - Chicago, Illinois

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I watched them tell people to take off their tiny little crossbody bags and put them on carryon. The staff was exuding so much power and control issues it was bizarre. I've flown with them always for years and I've never see them act like this. read more

Southwest has taken a nose dive. No availability to upgrade my middle row seat all the way in the back, that I was assigned when I checked in immediately. They made me put my carry on under the seat in front of me when there was bin space, so I had NO leg room when I was already in the middle seat. Most miserable flight of my life. I used to not care about flying and now I hate it. But thank god they can make a profit for their shareholders! read more

Every time no matter what time of year - Flights from Indy to Orlando have been seriously delayed !! This time we had to wait in 18 people on connecting flights that were delayed just so the greedy bastards could fill every seat on this flight ! No LUV for Southwest read more

Flew them 4 times this month, Feb. 2026. Internet, when it does work which is spotty, is to slow to be useable. Now flight attendants lie when I heard several nearby passengers ask to move their seats, even on 70% empty plane because of weight and balance problems. Prior to Jan. 27, 2026 this was NEVER a problem but suddenly now is?! read more

I went on a flight with my carry on bag. It has been let on the plane countless times. some jerk of a lady was extremely bitchy to me at the gate and made me check my bag because it was 1/4" too deep?? Like she got out a damn ruler. I wish I knew her name. She deserves to be fired. And if Southwest is pulling this petty shit when you PUT YOUR SUITCASE IN SIDEWAYS ON THE PLANE ANYWAY, I sincerely hope they go out of business. Chicago to MCO flight 3173. Whoever your gate attendant was, she's horrible and is being super rude to everyone. read more

If I could give zero stars for how I was treated by Southwest Airlines staff, I would. I was denied boarding today simply for calmly asking a question after being spoken to rudely by a gate agent. As I approached to board, the agent snapped at me, saying, "Why are you in the front? Go to the back." I complied without issue. When I got to the scanner, I asked, "Is this how we treat veterans?" and she immediately became defensive and said, "How would I know that? Is it written on your shirt?" I made it clear I was just asking a genuine question and stayed calm throughout. Still, she escalated the situation by calling over a supervisor. When I explained what happened to him -- again, calmly and respectfully -- he told me I was "too crazy to fly" and denied me access to the flight. Keep in mind, the original agent was actually still trying to let me board, but the supervisor overruled her. The supervisor, Edwin, refused to give me the gate agent's name -- only his own. I was told I would be rebooked, but that I'd have to cover my own hotel for the night. That's unacceptable, especially since I did nothing to deserve being removed from a flight. Even after speaking to someone above the operations manager, still no accountability. No apology. No resolution. Just a wall of silence and a ruined travel experience caused by unprofessional, disrespectful staff. If this is how Southwest treats paying customers and veterans, then leadership needs to take a serious look at who is representing the company at the gate. Edwin and the agent involved should absolutely be investigated, if not removed from their positions. Southwest, do better -- or replace the people who clearly don't reflect your core values. read more

Southwest Airlines - Airlines Near Me - Chicago, Illinois

Flight was great and on time. Southwest is so awesome since they offer such great bonuses on their rapid rewards points as well as companion passes (who doesn't love free flights) with very little work to do. I signed up for their credit card and my hubby did too. That gave us the points we needed to book flights as well as eventually earning the companion pass for 2 years free flights just for normal spending. I love travel and I can do more thanks to free flights! Planning travel is my favorite hobby! You can also be rewarded if you apply here and are approved for the card. Safe travels!! https://www.referyourchasecard.com/226n/4HUX0EOUYQ read more

Southwest Airlines - Pensacola air show was fantastic. Southwest points made this flight to see it possible. - Airlines Near Me - Chicago, Illinois