Hi, all!
My husband, daughter and I are planning a labor day weekend trip. We will leave Friday night and come home Monday night. (So just 3 nights)
we are located just outside of Chicago. We are fine flying (if we do fly it will be with southwest) or driving. Looking for recommendations on places you’ve been around Labor Day or have good things to say!

We are already going go San Antonio, Arizona, Boston, Disneyworld, and Buffalo/Niagara by Labor Day Weekend so we will avoid those locations. Thanks for the help!

Seattle, Las Vegas, Monterrey, San Francisco, Boston... all alive in early September...

Since you are going to Disneyworld, I'm guessing your daughter might be a little young for Las Vegas. How about riding the Amtrak City of New Orleans overnight to Memphis? It leaves Union station at 8PM and is in Memphis (on Main St.) in about 10 to 11 hours (6 to 7AM). There are a few things to see there other than Graceland. Across Main St. from the train station is the Arcade restaurant which was a favorite of Elvis. You might even be able to sit and have breakfast in a booth that Elvis sat in.

Have been to Colorado around Labor Day and it was great weather for hiking, fishing, horseback riding.

You didn't give daughter's age. SW flies into MHT - Manchester NH. Portsmouth NH is about an hour to the east. There's the Seacoast science center, boat rides, Strawbery Banke Historic area and Maine is just across the bridge. There's a water park just south of Portsmouth. We don't get there with our grandchildren but you might check to see if there are still some summer theater productions for children. Since schools usually go back the week before Labor Day, a lot of summer kid activities have probably ended.

From MHT, if you head north you have a choice of Lake Winnipesaukee area and White Mountains. Clark's Trained Bears, the Flume, etc are popular. My favorite is Squam Lakes Science Center in Holderness. You can also take a pontoon boat ride to see loons. Our grandkids enjoyed the coyote demonstration (and chose not to sit in the first row). There are docents walking around to make sure everyone is having a good time. One had a small owl on her arm and gave us a brief talk about owls.

You can go kayaking renting a two person kayak for parent and child. The rental place just outside Concord NH gives you the option of taking you to the Merrimack River for a half day paddle or you can stay on their river for an hour or two and paddle to a small secluded beach. Great fun to take a picnic lunch. The Merrimack River is usually very low that time of year and there are several places where you can enjoy a private beach. Despite being close to the city, this section is secluded so you won't see any houses until you get near the end. Should you stay in Concord NH there is also the Kearsarge Indian Museum and Little Nature Museum in Warner plus the Hopkinton State Fair is over Labor Day weekend. If it rains, SEE science center in Manchester is fun.

It really depends on your interests. Just be advised that there is heavy southbound traffic on Monday afternoon on I93 that gets clogged down around Concord NH because I89 from VT connects to I93 south of Concord. You can bypass this area by taking an alternate route.