The Most Efficient Way to Access the Center of Chicago
The airport you select when visiting Chicago and the airline you fly with will dictate how pleasant your overall travel experience will be. A vast majority will choose the sprawling O’Hare International Airport, but savvy travelers will prefer Southwest Airlines to Chicago Midway International Airport (MDW) and thus, flying with Southwest Airlines.
Why? Simply put. Travel offered by Southwest Airlines at Midway beats anything offered by other airlines in terms of cost, convenience, and stress level. Casual and business travelers alike appreciate the combination of Southwest Airlines and Midway, given the airport’s easier access to downtown Chicago, generous timetables, effective terminals, and increased baggage limits.
This final guide describes every reason why Southwest Airlines should be taken to Chicago Midway Airport, what services to expect at the airport, as well as travel tips and hacks that will make your trip easier.
Why Choose to Fly With Southwest Airlines
1. Cost-Effective and Straightforward Pricing
Southwest Airlines is well known for its fares, which are free from hidden fees. The airline industry is notorious for concealed charges, but here’s how Southwest is different:
Offers two complimentary checked bags on all fares
No change fees—ever
No cancellation fees
Partial refunds for Business Select and Anytime fares
Refundable fare options will never expire, allowing for unlimited reservation alteration.
The inflexibility that business travelers and families have to face is minimized with these benefits provided by Southwest.
2. Rapid Rewards and Companion Pass
Among domestic airlines, Southwest’s Rapid Rewards program is arguably one of the best loyalty programs. Southwest ensures earning rewards is hassle-free by having rewards points that never expire, along with accessible seats and unblocked seating.
Moreover, one of the most advantageous domestic travel bonuses is the Companion Pass, which allows bringing one sponsoring person for free to all flights for an entire year.
3. Dependable and Courteous Service
An airline regarded as approachable and polite is rare, and Southwest is consistently recognized for humorously professional flight attendants, along with its impressive customer approval scores. They maintain their top-rated customer satisfaction scores through systems simplification.
What Makes Midway Airport Preferable Compared to O’Hare?
While O’Hare’s (ORD) International Airport is Chicago’s largest gateway, for some travelers, Midway (MDW) makes more sense to access. Here’s why:
Closer to Downtown: Midway is approximately 10 miles from the Loop, compared to O’Hare, which is over 17 miles away.
Fewer Terminals: Smaller airports like Midway greatly lack in the number of terminals also makes navigating Chicago much simpler.
More Efficient Security: Fewer travelers passing through means that there will be less congestion at check-in, making delays even more minimal.
Reduced Weather Delays: Midway tends to outperform during operationally challenging weather conditions.
Southwest Airlines dominates the market at MDW, using the airport exclusively as its base and the Midwest hub for the airline.
Southwest Flight Routes to MDW
Midway is connected with more than 60 United States cities through Southwest Airlines’ non-stop services. These include:
Los Angeles (LAX)
Denver (DEN)
Dallas Love Field (DAL)
Phoenix (PHX)
Atlanta (ATL)
New York LaGuardia (LGA)
Orlando (MCO)
Las Vegas (LAS)
With such a vast network and for travelers from coast to coast, accessing Chicago is simple through Southwest.
Terminal Southwest Experience at Midway
Southwest Airlines operates at both Concourses A and B of Midway, which together comprise the single main terminal of the airport. Here’s what to expect:
Check In and Security
Self-service kiosks with streamlined baggage drop for checked bags
TSA PreCheck and CLEAR lanes offer faster screening for known travelers.
Lines are generally quicker moving when compared to major international hubs.
Gate Areas and Lounges
Podiums do not offer premium lounges, but Southwest gate areas are kept neat and orderly. They have ample USB outlets, comfortable seating, free WiFi, and auxiliary ports for effortless waiting.
Dining and Shopping
Local eateries: спад Reilly’s Daughter Pub and Big City Chicken—two Chicago classics.
Quikserve: Starbucks, dunkin, potbelly and more.
Retail: Hudson News, gift shops with items depicting the Windy City, electronics, and travel necessities.

Useful Tips For Flying With Southwest To Chicago Midway
1. Check in Precisely 24 Hours Before
Southwest employs open seating arrangements—boarding order is dictated by check-in time. For a favorable seat, check in 24 hours in advance to gain an A or early B boarding group.
2. Leverage the Southwest Mobile App.
Through the application, you can:
– Check in for your flight
– Access your digital boarding pass
– Track bags and receive updates about the flight
3. Maximize Rapid Rewards
Get a Southwest credit card to earn double or triple points for Southwest purchases and with its partners. Completing Southwest rewards transactions through the airline’s official page will allow you to earn all rewards offered.
4. Save on Ground Transportation
The Orange Line CTA train provides a connection to Midway and can take you to downtown Chicago for less than $3 in 25 minutes. While taxis and rideshares are available, public transport tends to be swifter and cheaper during rush hour.
5. Parking Suggestion
For the economy and daily lots at Midway, use ParkWhiz or SpotHero to find a cheaper reserved space. MDW flyers may take advantage of the Economy Smart Lot or off-site lots with shuttles offered for frequent travelers.
Best Timings to Fly for an Enhanced Experience
Booking flights before 8 a.m. increases value and minimizes delays.
Tuesdays and Wednesdays usually have lower fares with fewer crowds.
Cost-conscious travelers can take advantage of off-peak months: late September, January, or February.
Exploring Attractions Close to Midway Airport
Is there a flight planned from Southwest Airlines to Chicago Midway International Airport shortly? Consider checking out these:
Ford City Mall: Easily accessible via rideshare services.
Midway Plaisance Park: Offers beautiful locations for walking within the local area.
‘Taste of Chicago’ serves authentic Chicago deep-dish pizza close to Midway
Table of Contents
Southwest Airlines offers reasonable flight options to Chicago.
If you’re visiting the city for the Cubs’ matches, business meetings, or indulging in the Chicago pizza, Southwest Airlines, in conjunction with Midway Airport, has you covered every single time.
Benefits offered:
Affordable airfare
Strategic and easy-to-navigate airport
Great connections across the country
Free bag check, lack of fees, ease of transport, and ground stress-free.
There is no need to overplan your trip; with Chicago deep-dish pizza at your fingertips, everything is easy when using Southwest on your preferred dates.