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?

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Three Great Day Trips from Chicago

During our year in Chicago, I really wanted to make an effort to explore the rest of the Midwest. Since Chris worked on the weekends, we had to settle for places we could visit in a day. I’m a huge fan of day trips. It’s so fun to have a mini adventure and still come home to your own bed. Though we went on more than three day trips while we were in Chicago, today I wanted to share my three favorite trips in case anyone wanted some day trip ideas.

Starved Rock State Park in Utica, Illinois
Time from Chicago: 1.5 hours
What to do: In the fall, hike and enjoy the fall color. Take a trolley tour to get an overview of the park. In the spring, hike to the waterfalls.
More information: Starved Rock State Park blog post
Bonus: Stop by Two Girls and A Cupcake for a post-hiking treat!

When I was researching day trips from Chicago with gorgeous fall color, Starved Rock State Park kept popping up. I could see why from the moment we got there. The colors were stunning, and the canyons were fun to hike. We had planned on a return trip in the spring to see the waterfalls but had to cancel when I got sick. It’s definitely on the list for the next time we’re in the Midwest.

Indiana Dunes State Park in Chesterton, Indiana
Time from Chicago: 1 hour
What to do: Climb the dunes and be rewarded with amazing views of Lake Michigan
More information: Blog post mentioning our Indiana Dunes adventure
Bonus: If you don’t feel like hiking, there is a beautiful beach close to the Indiana Dunes.

I never expected for climbing the Indiana Dunes would be so hard! Don’t worry, there are easy trails, but Chris accidentally picked the most strenuous trail for us. When you are wearing flip flops a little too big for you, the result is entertaining. Still, the hike was worth it for all the pretty views of Lake Michigan.

Lake Geneva, Wisconsin
Time from Chicago: 1.5 hours
What to do: Walk around the cute downtown area. Shop. Take a boat tour on Geneva Lake to see the mansions. Walk the trail for a closer look at the mansions. Visit Black Point Estate.
More information: Fall color boat tour on Geneva Lake blog post
Bonus: Have lunch or dinner at Oakfire for some delicious pizza and a nice view.

I loved all the day trips we did, but the one to Lake Geneva, Wisconsin, was my favorite. I loved walking around the downtown area, but the boat tour was the highlight of our day. I loved seeing all the mansions and hearing stories about the families who built them. The stunning foliage made it the perfect fall adventure.

Are you a fan of day trips? Where have you visited?

Road Trip Around Lake Michigan: Seven-Day Itinerary from Chicago

Before we went on our Lake Michigan Circle Tour road trip, I was disappointed that I couldn’t take Christopher on a “bigger” vacation this year. Once I started planning, I realized there was so much I wanted to do and wished we had more time. By the time the trip was over, Chris and I were discussing moving to the Midwest someday.

We visited wineries, enjoyed scenic hikes, had amazing meals, and saw three of the Great Lakes. Since we got home, all we can talk about is doing this trip again someday. Like with my California road trip post, I will be linking up the individual posts to this itinerary as I do them.

Day One: Chicago to Grand Haven, Michigan 

Highlights: Did a chocolate tasting at The Chocolate Garden in Coloma, visited the lighthouse in South Haven, drove through downtown Saugatauk, saw the Holland lighthouse, then spent the afternoon in Grand Haven, eating great food and enjoying the lighthouse and boardwalk. 

Spent the night in: Grand Haven

Day Two: Grand Haven to Traverse City 

Highlights: Had breakfast at Morning Star Café, drove to Ludington and hiked to the Big Sable Point Lighthouse, then headed to Manistee to see the lighthouse. Next, we headed to the Arcadia Inspiration Point for stunning views of Lake Michigan. Spent the afternoon at the Sleeping Bear Dunes National Lakeshore with three major stops: Glen Haven, the Pyramid Point Trail, and Pierce Stocking Drive. Finished a great day with an amazing dinner in Traverse City.

Spent the night in: Traverse City

Day Three: Traverse City and Old Mission Peninsula

Highlights: Drove to Leland to see the historic fishing village, then headed to the Leelanau Peninsula for cider tasting at Tandem Ciders. Spent the rest of the day on the Old Mission Peninsula: saw the Old Mission Lighthouse and did wine tastings at two wineries: Chateau Chantal and 2 Lads Winery. Had dinner on Fleet Street and capped off our day with cherry products at the Cherry Republic.

Spent the night in: Traverse City

Day Four: Traverse City to Mackinaw City 

Highlights: Drove to Charlevoix to see the lighthouse, then headed to Petoskey to explore the Bayfront Park and the Gas Light District. Took the scenic drive through the Tunnel of Trees (M-22) and had lunch at the famous Legs Inn. Drove to Mackinaw City, dropped off our bags at the hotel, then headed to the beautiful Tahquamenon Falls State Park.

Spent the night in: Mackinaw City

Day Five: Mackinac Island 

Highlights: Took a ferry from Mackinaw City to Mackinac Island with a special ride under the Mackinac Bridge. Took a carriage tour to get an overview of the island. Ended our tour at Fort Mackinac, then spent a few hours trying different fudge shops and exploring the island.

Spent the night in Mackinaw City

Day Six: Mackinaw City to Door County, Wisconsin 

Highlights: Visited the Seule Choix Lighthouse, saw Kitch-iti-Kipi, saw the Wagner Falls, and enjoyed a boat tour on the Pictured Rocks National Lakeshore.

Spent the night in: Sturgeon Bay

Day Seven: Door County 

Highlights: Went on the Door County Trolley Tour, explored Door County, saw the waves crashing at Cave Point County Park, and capped off our day with a fish boil.

Spent the night in: Sturgeon Bay

Lake Michigan Circle Tour Road Trip Post Directory:

Quick Thoughts

Seven-Day Itinerary from Chicago
South Haven Lighthouse
Big Red Lighthouse
Grand Haven, Michigan Food Adventures
Grand Haven Lighthouse and Boardwalk
Hiking to the Big Sable Point Lighthouse
Big Sable Point Lighthouse
Arcadia Inspiration Point Scenic Overlook

Fall Colors on the Lake Geneva Cruise Line Full Lake Tour

Since we don’t get a lot of fall color in Texas, Chris and I have been trying to enjoy it as much as we can during our year in the Midwest. When Chris got his first day off in nearly two weeks, I planned a day trip to Lake Geneva, Wisconsin, for beautiful fall foliage views and gorgeous mansions.

Lake Geneva is sometimes called “The Newport of the West” due to the many mansions situated along the shores of Geneva Lake. (Note: The town is called Lake Geneva while the lake is called Geneva Lake). Some of the famous families who currently have or used to have estates around the lake are the Wrigley Family (known for chewing gum), Wacker Family, Schwinn Family (known for bicycles), and the Wacker Family (a prominent Chicago family—Charles H. Wacker championed the Burnham Plan for Chicago and was the director of the 1893 Columbian Exposition).

We opted to take the Full Lake Tour of Geneva Lake from the Lake Geneva Cruise Line, which was a two-hour cruise aboard the Walworth II, a boat that is still used as a mailboat during the summer. I loved our time cruising along the lake, hearing stories of the families who have built estates there and seeing the vibrant fall colors.

It was the perfect fall adventure. The fall color was some of the most stunning I have ever seen, especially along the lakeshore. I enjoyed seeing all of the massive estates while Chris loved googling more information about the families. If we lived in the area, Lake Geneva is a place I would visit every year.

Quick Thoughts: Lake Michigan Circle Tour Road Trip

Hello, friends. I am so glad to be back on the blog this morning. I decided to go ahead and take Friday off from blogging last minute because my in-laws came to visit. Thank you so much to my wonderful guest posters for holding down the fort while I was gone.

After several stressful months, this trip was exactly what we needed to get us through the rest of the year. Honestly, going into the road trip I was a little bummed that we couldn’t do something a little more “exciting” since this is Christopher’s only real vacation until the end of intern year in June, but everything turned out so much better than I expected. I easily fell in love with the Midwest. Chris and I were constantly talking about how great it would be to live in this area (minus the winters!)

We crammed as much as we could into each day, but there was so much more we could have done. One of the things that surprised me was how good the food was—Chris keeps “joking” about driving the three hours back to Grand Haven just so we can eat.

Skyler was such a trooper. She loved all the hiking we did. Those little corgi legs were trucking all over the place. The hardest part of hiking with Sky is people constantly stop us to ask about her. Don’t get me wrong—I love talking about her, but when you are on a five-mile hike, sometimes all you want to do is get to your destination.

Even though we mostly stayed on the Lake Michigan Circle Tour route, we made detours so we could see three Great Lakes on this trip—Lake Michigan, Lake Huron, and Lake Superior. We have had people from the Midwest tell us they don’t have to visit an ocean because they have everything they need at the lake, and I can see the appeal. The water, especially at Lake Superior, is so clear and beautiful, and you don’t have to deal with it being salty.

I am so excited to share our trip with y’all. I hope it inspires you to give Michigan and Wisconsin a try.