Tips for Navigating Chicago’s Midway & O’Hare Airports

If you are anything like me, travel—especially air travel, creates a ton of stress. So that’s why I have compiled this list of tips for navigating both O’Hare and Midway airports like a frequent flier, even if you only fly once or twice a year. So pack a bag and focus on your chosen destination, not the battle for the arm rest once you board the plane.

Deciding Which Airport to Use

As north siders, we typically use O’Hare airport because it is only a short drive away. But here’s the thing…I have been making a mistake. For just about all of my life.  Yikes. But now I know that if I am traveling domestically, Midway is the way to go since it is a smaller airport and as a result has less delays. If you are traveling out of the country, O’Hare is the airport for you. Oh, and another tip? Fly either out of or into Chicago on a foreign airline to avoid delays.

General Planning Tips

When booking a flight, always look for the bigger plane option. Why? For a few reasons. Not only do larger planes provide a smoother flight, but they also get priority since larger planes typically have additional and further flights to make in the day. Any air traffic control employee will tell you that the size of the plane always matters.

Also be sure to book the earliest flight possible to avoid delays and enjoy as much of your trip as you can. There are only 24 hours in a day, no matter where you are.

As I wrote in my previous article about the best apps for traveling families, you definitely want to look into Gate Guru to learn about the airports you are traveling to (restaurants, amenities, and other perks are listed) and Seat Guru to ensure you get the most comfortable seat on the plane as possible.

Oh, and don’t forget to check out this viral article about “the magical day to buy plane tickets.” Can’t wait to try it out and see if it works for us!

Lastly, for you parents traveling with kids and not sure what you can or cannot get through security, here is the TSA policy that I recommend printing and having on hand….just in case.

Car Services

Don’t want to park your car at the airport while you are away? I don’t blame you. That’s why I have done extensive research on car services that cater to families, including providing car seats when needed. My top picks include Ride BLK, Going Green Limousine, and Escalady of Four.

Want to drive your own car with your own car seats but don’t want the hassle of parking in the garage and finding your way to the airport yourself? Then be sure to use my favorite travel hack when traveling though O’Hare Airport: O’Hare Personal Valet. They will meet you at the curb, help you unload your vehicle, and wish you safe travels before parking your car in a safe location. Once you are back at O’Hare, simply confirm that you are ready to be picked up, agree on a pickup location via text, and have a warm and ready car waiting for you to go home. Read my friend Cassandra’s review of O’Hare Personal Valet here.

Navigating O’Hare Airport with Ease
How to Get There

If you aren’t using a service like O’Hare Personal Valet, look into the different remote parking options (all include a shuttle service to the airport) or be sure to use the CTA Blue Line. Popular parking options include Blue Sky Parking, Park ‘n Jet, and general airport parking (stick with Lot E…you won’t even need the shuttle!).

When to Travel

As I’m sure you’ve heard from planes flying over Chicagoland, O’Hare International Airport is a very BUSY airport. Its busiest times? Monday morning, Thursday afternoon, and all day Friday. If I were you, I would avoid traveling during those times.

Inside the Airport

Terminal 2 is my favorite terminal to use at O’Hare. Why? Because it isn’t as crowded with all of those American and United Airlines flyers. But there are other awesome things going on at Terminal 2, such as:

Large kids’ play area—which is never, EVER crowded

Hilton Hotel—Even if you don’t have to stay overnight (which would be strange as a Chicagoan), the Hilton hotel is a GREAT resource for you if your flight gets delayed. Why? Because you can pay a $20 daily fee to take advantage of its gym. And by gym, I mean steam room, sauna, lap pool, hot tub, full service locker rooms….absolutely glorious.

United Club in Terminal 2—This newly renovated club is free for members but charges a $50 daily fee. With an open bar, snacks, wifi, and hot showers, the United Club is a great way to unwind without having to leave the airport. You can also take your drink to go…but sadly need to down it before boarding the plane.

Airport food has gotten a major upgrade in recent years, and there are some pretty delicious ways to eat and drink your way to happiness. My favorites? Tortas Frontera, Stefani’s Tuscany Café, Goose Island Brewing Company, and Greek Place.

Have kids on your hands? Then be sure to take advantage of the mother’s rooms on Terminal 1 on B Concourse across from Gate B10, the Terminal 3 Rotunda, and Terminal 5 near Gate M14. There are also some great art displays, including a fighter plane, to enjoy in Terminal 3.

Want to enjoy some beautiful Chicago weather? Relax with drinks and appetizers in the O’Hare Urban Garden in Terminal 3, or take advantage of the FREE adjoining yoga studio. They will provide you with the mats, quiet, and relaxation….just don’t forget to say “Namaste.”

Oh, and don’t forget that O’Hare has TONS of workspace and charging stations set up throughout the airport…don’t feel like you have to sit on the dirty floor next to the first outlet you find.


Tips for Getting Around Midway Airport


Getting There

I’m not going to lie…Midway Airport is not the most convenient airport to get to. If taking public transportation, become accustomed to the Orange Line. If you are driving yourself, look into the two main parking options: Reserved (an additional $10 on top of regular parking fees) or Economy ($15 a day with shuttle provided to airport). If you have someone picking you up or dropping you off, have them meet you inside the daily parking garage (the first 10 minutes are free). It is a nice way to unload and load up protected from the Chicago elements without people screaming at you to hurry up.

When to Travel

The busiest times for travel at Midway Airport are between 5-8 a.m. and 3-6 p.m. Don’t believe me? Just look at the security lines. Oh, and speaking of security lines. Avoid the far right security line…it might look shortest but it winds around and will undoubtedly be longer than the other lines.

Inside the Airport

Midway Airport is much cozier than O’Hare, and as a result easier to navigate. The Concourse has everything you need—you will find a Mother’s Room, Yoga Studio, USO Center, as well as changing art exhibits to enjoy.

Restaurants to enjoy while at Midway: Reilly’s Daughter, Harray Caray’s Seventh Inning Stretch, Illinois Bar and Grill, Nuts on Clark, Manny’s Deli, and Pegasus on the Fly.

Lastly, don’t forget to charge up your electronics at the charging stations at A3, B10, or B12. My rookie parent mistake was having an uncharged DVD player on someone’s first flight—needless to say, it didn’t go so great.


I am by no means an expert traveler…what O’Hare or Midway travel tips did I miss? Please share them below so we can all learn something new!

Happy and Safe Travels!
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  1. Robin Rue (@massholemommy) says

    This is super helpful! I had a quick layover at O’Hare once, but would love to actually fly in there to spend some time in Chicago one day.

  2. Jeanette says

    I have been to both airports and I prefer Midway. These are great tips! I think you have some awesome tips and those that go to Chicago needs to read this.

  3. lisa says

    There is a lot of great info here. I use Midway almost every time I fly. I occasionally fly through O’Hare but I much prefer the ease of Midway.

  4. Dina says

    I’ve been in Ohare and considering it was my first time there and I had to mkae a connecting flight I thought it was pretty easy to navigate. 🙂

  5. Up Run For Life says

    I haven’t been to O’Hare. I have only flown a few times in my life. It was usually a journey from NC to Tx. DFW airport is our major airpot. We also have the smaller Dallas Love Field. Parking at the airport can be stressful if you don’t give yourself plenty of time especially during peak times (holidays, spring break, summer).

    • Amanda says

      I never thought about it either until I researched this article. Now I’ll always look into the size of the plane!

    • Amanda says

      O’Hare is a hub for United Airlines so tons of people travel through O’Hare…hopefully this article will reduce their stress!

    • Amanda says

      Or even for those who travel through Chicago. It has some great suggestions for layovers and ways to relax while traveling.

  6. Michele D says

    I’ve never flew into Chicago’s airports before but if it’s anything like Orlando, I bet I’ll get confused. I live here and still get confused. LOL Thanks for the tips. Would love to visit there one day.

  7. Kathy says

    This is very helpful. I’ve never even flown in a plane before though. I have been to Chicago once though. It’s a beautiful city.

  8. jo says

    I’ve had one connecting flight in Chicago O’hare once and my oh my, it’s huge! LOL! I wish this has been posted sooner so I didn’t get bored there for 5 hours. I just stayed at Starbucks that time because I don’t know where else to hangout. LOL! I wish I visited at least one of the restaurants you mentioned here. 😀

  9. Becca Wilson says

    I have never flown. I know that sounds crazy in today’s world! If I ever do get the chance to go here I will know what to do!

  10. Roman M says

    Midway airport is very confusing once you leave the terminal and try to get to the Orange line.
    Yes the signs clearly point where you have to keep walking to but once you get near the doors of the parking
    garage that’s where it gets confusing. The elevators are right there as well and nothing is marked to show that you have to take an elevator up to the third floor to access the Orange line. I found this out the hard way last night. Once you get inside the elevators it does say to press 3 for Midway Orange line.

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