Help me plan a fun overnight trip this weekend, near Chicago
August 17, 2016 7:51 AM   Subscribe

The grandparents are coming and keeping the kids overnight! Yay! We haven't had free time in so long we don't know what the options are for us to do with it! Boo. Halp!

My husband and I would like to not be total lame-o's, and have a fun overnight trip. We're looking for this weekend, Saturday morning to mid-day on Sunday, within a 2-hour radius of Chicago northwest suburbs. We had thought of staying in downtown Chicago and seeing a musical, but most everything seems to be between productions this weekend.

So - suggestions for where we could go, where we could stay, what would be fun to do? Lake Geneva area is also an option, but I would love to hear your favorite things to do in that vicinity. Also - the biggest problem here is that we don't know what we don't know, so off the wall suggestions are absolutely welcome.
posted by telepanda to Travel & Transportation around Ingleside, IL (6 answers total) 1 user marked this as a favorite
This Saturday is the Harbor Park Jazz and Blues Festival. I went last year and it was the same headliner band and they were fantastic. I go as early as possible-- there are several other featured performers and activities-- find a hotel in Kenosha and go to a beach the next day and to Tenuta's for a takeout lunch.
posted by BibiRose at 8:16 AM on August 17, 2016

I'd spend the night near Great America and go there for a day without kids! Or maybe go explore Madison or Milwaukee, WI?
posted by hydra77 at 9:23 AM on August 17, 2016

Seconding Madison. You can visit it like grownups, or like college kids on a bender.
posted by JoeZydeco at 10:43 AM on August 17, 2016

If you do Madison I'd highly recommend the Concourse Hotel and staying on the floor with happy hour (Governor's Club). We also had a great stay at the Hampton Inn and Suites downtown (note that the pool for this tends to have kids around.) College move in is Aug 30. We were there last weekend and there was already some activity (e.g., random bookcases on the curb) but it wasn't crazy yet.

We have also done a staycation in Chicago downtown (Hotel Palomar) with just dinner reservations planned, a hotel with a whirpool, and spent the time just visiting old haunts without an agenda as we did in our kid-free days and had a wonderful time.
posted by typecloud at 12:02 PM on August 17, 2016

Stay in Milwaukee's Third Ward neighborhood. There's a brand new Kimpton Hotel and it's walking distance from this weekend's Irish Fest, on the lakefront Summerfest grounds.
posted by quarterinmyshoe at 12:29 PM on August 17, 2016

" We had thought of staying in downtown Chicago and seeing a musical, but most everything seems to be between productions this weekend."
I'd still try to stay in downtown. Try to see Second City and eat at an amazing, not at all kid-friendly restaurant. Get a nice hotel room and book a massage or two or three.
OR - and you'll either love this idea or hate it - what about a trip to Springfield to explore the Lincoln history? There's the Lincoln tomb and the presidential library and all the historic sites. I know that's a kid-friendly type trip, but I think it would be great to do that alone and really enjoy it without making my kids pretend to be interested.
Have a great weekend!
posted by areaperson at 1:10 PM on August 17, 2016

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