The Siberian American: Best Weekend Trips from Chicago

Wednesday, April 5, 2017

Best Weekend Trips from Chicago

It’s been a while since I’ve done a Chicago travel post, and I still have so much to share about our year in the Windy City. Last year I shared my three favorite day trips from Chicago, so today I wanted to share my favorite weekend trips! Chris didn’t have many weekends off last year, so we saw most of these places on our week-long road trip around Lake Michigan, but they are completely possible to do in a weekend!

Grand Haven, Michigan
Time from Chicago: 172.5 miles, about three hours
What to do: Walk around the boardwalk, see the Grand Haven Lighthouse, and eat all kinds of yummy food.
More information: Grand Haven Lighthouse and Boardwalk and Grand Haven, Michigan Food Adventures 

If you followed our Lake Michigan Circle Tour, you heard me mention Grand Haven a lot. Chris and I were totally surprised by this gorgeous little town by the lake. If we had been in Chicago for more than a year, I know we would have visited multiple times. Not only is it beautiful, it had some great eats!

Traverse City, Michigan
Time from Chicago: 319 miles, about five hours
What to do: Sleeping Bear Dunes National Lakeshore, visit the wineries at Old Mission Peninsula, Leland, pick cherries or eat cherry product, enjoy many amazing restaurants
More information: Pyramid Point Trail at Sleeping Bear Dunes National Lakeshore

Traverse City is slightly pushing it for a weekend trip, and I think this city deserves more than two days, but if a weekend is all you have, it’s still worth going! One of these days (soon), I will write posts on all we did in this amazing city, but for now I will say it had some of my favorite views and eats of our entire trip. The wineries were wonderful, and Sleeping Bear Dunes National Lakeshore is stunning. It’s definitely a place I would love to visit again in the future.

Door County, Wisconsin
Time from Chicago: 244 miles, about 4.5 hours
What to do: Tour all the towns, shop, go to a fish boil, visit Cave Point County Park, eat all the cherry products

If you are looking for a relaxing weekend trip from Chicago, Door County is the perfect spot. It’s full of beautiful views and lots of great shops and restaurants. I even enjoyed the local tradition of a fish boil, even though it sounded a bit gross to me before we went!

Bonus: Galena, Illinois
Time from Chicago: 163 miles, about three hours

Galena was the trip that didn’t happen. We had plans to go in June before we moved back to Texas, but then I got sick, and it wasn’t possible. I wanted to included as part of this list because Galena is constantly voted as one of the best small towns in America, and about a million people told us to go while we lived in Chicago. We definitely hope to make it there someday!

Where do you like to go on weekend trips from your city?


  1. yay for Traverse City!!! There is so much to do in the area that you could easily spend a week in TC :)

  2. Chicago is one of my favorite cities! My brother lives out there and has traveled to Wisconsin a few times. I've always heard some nice things about Michigan and feel like I need to visit at some point. Beautifully Candid

  3. So many great places in this post! I haven't been to Grand Haven or TC in a few years, and have never been to Door County (or WI at all), but always hear such good things.

  4. Ok I lived in Chicago 28 years and have been to zero of the places you mentioned! I have had so many people tell me about Door County, but I never was able to make it there...I've heard it absolutely amazing!! I've heard great things about Galena too!

  5. I always hear the best things about Michigan. All the pretty water fronts...

  6. This makes me really want to go on a weekend trip. Well, I guess I technically am...I'm going to Houston next weekend but I don't ever count that because when I go it's not really to ever do anything new. It's to visit with friends from when I lived there & do all the things I miss from there. So what I want is to do all the new things lol.

  7. I've heard a lot about Traverse City from Jordan!

  8. I know that a ton of people end up visiting Illinois for Chicago, but there really is so much to see and do around the area! I love all of your posts about your trip around Lake Michigan so I know that I'd love a weekend trip to Grand Haven!

  9. I love the great lakes region, I've heard great things about all of those places. Every summer I think that I want to go back up there. One of these days I'll get around to it! Excited to know you have posts if we end up needing them! XO - Alexandra

    Simply Alexandra: My Favorite Things

  10. I live about 40 minutes from Grand Haven. Love going to the beach out there in the summer. Traverse City is great too. We need to do some trips to Wisconsin!

  11. Weekending trips are the best and sounds like there are so man great ones to take from Chicago! It's our favorite thing to do here in Boston! xo, Biana -BlovedBoston

  12. Such gorgeous places so close to the city to explore! My husband is in Chicago right now for work and, while I was slightly jealous I couldn't join, he says the weather is pretty miserable so I'm glad I didn't pack up and go just because I love Chicago so much. I think September is the perfect month to visit when I go in the future.

  13. Door County - awhoo hoo! I should, at some point, hit up the locations in Michigan. I've never been to either place before.

  14. I feel like some of the Michigan ones are do-able from Ohio. (I should probably look at a map before I say that...) The lakefront towns are just so, so adorable and whimsical!

  15. I've heard a lot about Door County, and have always wanted to visit while driving through. So many beautiful places to check out close to one of my favorite cities <3
    Green Fashionista

  16. This list looks pretty awesome. Adding it to my list for when I get to Chicago.

  17. I've never been to any of these places, or Chicago, so I think I need to plan a trip!

  18. I love keeping a running list of weekend trips like these! You never know when you might catch a break and get two days in a row off!

  19. We lived 3 hours from Chicago for a few years, so Chicago WAS our great weekend trip idea. :P We've also gone Grand Haven, although that was just a daytrip since we were pretty close, and spent an anniversary in Traverse City--fun!


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