Travel - Chicago,IL

I would check with Southwest. A lot of airlines do not allow for the double strollers to be gate checked. I was able to gate check mine because I disassembled it and put it in a bag, otherwise, American wouldn't let me gate check it. I would get a bag for the booster seat, but that's a personal preference, I see people all the time just put it in a clear bag. The car seats should check for free as well as the stroller. With 3 tickets on Southwest, you get 6 free checked bags, not including the car seats and stroller. Is the pack n play going to be one of the 6 bags? If not, there will be a charge of $50 each way for the pack n play. For $100 you can either rent one or buy a cheap one when you get there. Also, Southwest needs proof of age for the baby. When my daughter was 4 months old, they asked for proof of age. I brought her newborn discharge papers from the hospital because I didn't have a birth certificate yet. After that I got a birth certificate and used that.

Everyone has given you great advice. We just flew with our 3 month old on Southwest and boarded between A and B with the Family Boarding. The flight attendant checking us on the flight told me that pregnancy was considered a medical condition and will upgrade you to pre-boarding status. She winked and said I could use that for the flight home to make sure I got us good seats. We used the red bags from Buy buy baby to protect the stroller and car seat. I was told we are allowed one car seat and one stroller per kid.

If the flight isn't full, Southwest will let you bring the infant seat on the plane, but it has to go in the window seat...and you won't be able to all sit together. They can't tell you if the flight is full until you check your bags. It's so much easier if you can keep the baby in the car seat. If you lift the fabric on the carrier (near the baby's feet), there are "hooks" so that you can loop the seat belt. It's very tight and secure. You have to log in EXACTLY 24hrs before your flight to get in the A boarding group. Otherwise, SW does family boarding between the A and B groups, and you'll be a little farther back in the plane. Have your husband and 4yr old sit behind you and the baby so if your daughter kicks the seat or is prone to pushing her feet in the chair in front of her, it will be in your seat or the baby's.

I also highly recommend a portable DVD player, especially if you have a more active daughter. If she's pretty good with books and activities, she may be fine since the flight isn't too, too long. Bring lots of snacks, stickers, etc to keep her occupied. Good luck and have a great trip!

You can check the stroller at the gate.

Give yourself lots of time, and bring lots of snacks.

An extra change of clothes for the kids and you is also important.

I hope your trip goes well!
I would not recommend a lap baby on a plane. Turbulence (or the unthinkable) could so easily be fatal. I've flown with 4 kids and they were all under age 7, all in carseats on the plane. Now, 2 kids will be much easier for you! :)
I wouldn't trust a 4-year-old to sit properly in a booster in the car. While the absolute minimum is 40 lbs., it's best to wait until age 6. That being said, we just started and my 6-year-old is still booster training because he's learning the rules. I can't imagine that at age 4. I would go out and get the Evenflo Maestro. It's not very expensive and it goes to 50 lbs. My 5-year-old used it on the plane and rental car and it's a breeze to install with the seatbelt. It's very, very light!
Be safe, and have fun!

The stroller and car seat should be gate checked without a problem!

We have checked a pack-n-play before. There are no issues with it, as long as it is within the dimensions and weight alloed by the airline. They are pretty small so there should not be any problems with it, but you can go online and check the dimensions, then measure, so you don't end up with a fee for a "large" bag.

As for the booster, you don't need a bag, but might want one to keep it clean. At the airport counter, they sometimes have clear plastic bags (like a large trash bag) that they can put it in, but not always.

Don.t worry too much! The day will come and then it will go, you will all survive, although you might end up taking some headache medication at the end of the night! Good luck!