From Cincinnati, one of our favorite destinations is Chicago. With Southwest Airlines flying from Cincinnati to Chicago Midway Airport, we have been there on $49 flights (about 2500 Southwest points) several times. Since we are often staying in Downtown Chicago, we have done a bunch of research to find the best way to get from Downtown Chicago to Midway Airport (MDW). So I thought I would share with you some of my information to help you figure out the best way to get from Chicago to Midway airport.
Downtown Chicago to Midway Airport by Uber or Lyft
Uber has an estimated price of $20-30 to go from Downtown Chicago to Midway Airport, though obviously that depends on your destination in Chicago and probably time of day (how long it takes)
Lyft is similarly priced from Downtown Chicago to MDW though both Uber and Lyft often are running promotions especially in Chicago so be sure to check with them before you go
[The time my Lyft driver went the wrong way down a one-way street]
If you do sign up for Uber or Lyft, signing up through my referral code you will get you up to $10 off on your first ride.
Getting from Downtown Chicago to MDW by taxi
You can absolutely take a taxi from Downtown Chicago to Midway Airport but it will be fairly expensive. Depending on where you are coming from in Downtown Chicago, a taxi from Chicago to Midway is likely to cost anywhere from $35 to $50, exclusive of tips and tolls.
If you do want to take a taxi from Downtown Chicago to Midway Airport / MDW, you’re likely to save money by using a service like Carmel Limo — plus you can save $4 off using this link.
And obviously you will be in a car, so subject to Chicago traffic, especially if you’re traveling in rush hour (which seems like every hour!)
How to get from Chicago to Midway Airport by bus
You can find several express buses that go from Chicago to Midway Airport, in the $15 to $20 (one-way) range. These are large buses designed for airport runs, so most of them should have plenty of storage underneath the seats for luggage. GO Airport Shuttle is one such bus – it costs $15-25 one-way. Try coupon codes GOWEB or GOSHARED to get 5% or 10% off
Remember, buses also go on the road, so when going from Chicago to Midway Airport by bus, you’ll be subject to traffic during peak traffic periods.
The cheapest and best way to get from Chicago to Midway Airport
While taxi, Uber, bus and even other ride share services or limos are all options to get from Downtown Chicago to Midway, in my opinion, the absolute best way to get from Midway Airport to Chicago is by train / subway
Another advantage of taking the train from Downtown Chicago to MDW is that you’re not on the road (duh), so you don’t have to deal with any Chicago traffic.
Step by step instructions for riding the Orange Line train from Chicago to Midway Airport
Depending on where you are at in Downtown Chicago, find your closest subway / El stop. Most if not all stations have areas where there are vending machines that sell Ventra cards. You will need a Ventra card to ride the train from Chicago to MDW but you have a couple of options, depending on what you’re looking for. You can buy
- 1-Day CTA Pass for $10
- 3-Day CTA Pass for $20
- 7-Day CTA Pass for $28
Or just buy single use cards. If you don’t have a Ventra card, you can buy one through these vending machines – it costs $5 but you can get the $5 refunded to you if you register the card within 90 days, The CTA Orange Train costs $2.50 per person. Kids ages 7-11 pay half fare ($1.25) while children 6 and under ride free. The Orange Line trains run from about 4:30 a.m. until about 1 a.m. on most days.
Once you’re on the train, then just ride the train until you get to Midway Airport. The Orange Line runs clockwise around Downtown Chicago in the Loop, and then there are 8 stops after you leave the loop until you get to MDW which is at the end of the line.
Once you get to Chicago Midway Airport (MDW), follow the signs to the airport. You will go down a corridor and around a few hallways – it’s all enclosed inside – just follow the signs.
I hope this guide has helped you travel from Chicago to Midway Airport – enjoy your travels! If you need to make this a round trip, check out our guide on the cheapest and best way to get from Midway airport to Downtown Chicago
What are your tips for the cheapest and best way from Midway Airport to Downtown Chicago
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
Of course you take the subway. Same thing for O’Hare, take the Blue Line downtown. Why sit in traffic and spend 10x to 30x as much depending on traffic when you can spend $2.50 and do it in good time.
I always take the train from/to the airport. It’s fast and the cheapest option and usually the best.
Duh
I lived there for a long time and yes the train is the cheapest way, but not always the best way. If you are quite a distance from a train station you have to allow for that, and then your wait at the train station. Sometimes Uber is just the better method.
Senior fares??