Chicago To Galena Road Trip: Must See Stops in Illinois USA

Last Updated on February 1, 2023

Galena is a lovely little town close to the Iowa border. You can find my full guide to Galena here: 10 Fun Things To Do In Galena IL, USA. It’s quite a nice easy drive from Chicago, making it a good option for a day trip from the city. In this post I share several must see places along the route from Chicago to Galena IL!

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Chicago To Galena

How Far Is Galena From Chicago?

🚗Distance: 164 miles

🕚Drive time: 2hr 30

🍔Where to eat along the route: The Rafters in Lena

🏨Where to stay in Galena: Chestnut Mountain Resort

The easiest route to take from Chicago to Galena is the I-90 to exit 17 at Rockford, and then the rest of the way on Hwy20. Route 20 is actually the longest route in the US, stretching from Massachusetts all the way to Oregon on the opposite side of the country, a journey of 3365 miles.

It is possible to take Route 20 the whole way from Chicago but the I-90/Hwy20 is the faster option and still has some fun things to see and go along the way. Keep in mind that the I-90 is a tollway and you will pass through a couple of plazas before turning off for Hwy20. Tolls can be paid online or if you are a frequent traveller, the I-Pass is the most convenient option.

Things To See & Do Between Chicago & Galena

South Barrington

Depending on how you are travelling may determine on when and where you want to stop to eat etc. If you are flying into Chicago O’Hare before travelling on to Galena, you may be after something to eat sooner, rather than later. South Barrington has a cute outdoor shopping mall and several options for places to eat. Georgio’s Chicago Pizzeria & Pub has good food!


For me, Rockford was always the milestone when travelling between Chicago and Galena. I would refer to it as the ‘water park junction’ as Hurricane Harbor is right on the side of the road where the I-90 and Hwy20 meet…once you reach the water park it’s time to turn off!

Hurricane Harbor is owned by Six Flags, who also operate Six Flags Great America in Gurnee, just outside of Chicago. The water park is quite small, I visited on one of their discount days which made it good value for money. As an adult I’m not sure it would be worth paying full price as many of the rides are aimed at younger visitors. Wipeout (a vertical looping water slide), Double Dare Drop, Typhoon Terror and Tidal Wave are the main high thrill rides.

Related reading: The Best Amusement Parks In The Midwest USA

Another stop in Rockford is the Midway Village Museum. The museum is a living history museum with a Victorian village and has many displays about life would have been like in the 1900’s. They also hold an annual Sock Monkey Festival! Sock Monkeys were first created using Rockford Red Heel socks. There is a permanent exhibit year round looking at how the monkeys began and their progression over the years.

Unfortunately I never made it there, however I hear great things about the Anderson Japanese Gardens. I love Japanese gardens and it looks like a lovely place to visit! They also offer various yoga and meditation sessions at the gardens to help you to relax and connect with nature. You can find out more information on the Anderson Japanese Gardens website.

⛽️Fuel stop: A great place to stop for fuel or a toilet break is the Road Ranger in Winnebago IL. It’s almost at the halfway point between Galena and Chicago. Just after here, the road then changes from 2 lane to one, so it can be slower going. Especially in winter this part of the route can get quite bad, there are lots of hills and corners which get slippery in the snow.


🗺The Rafters, 9426 W Wagner Rd, Lena, IL 61048, United States

I love love LOVE The Rafters restaurant in Lena! There two dining areas: the main restaurant (with a water feature) and the bar area. The food is awesome and they have good priced weekly specials.

Next door is the Lena Brewing Company, which also offer tours for $10. They often have really unique flavours such as Caramel Pecan Coffee Stout and Chocolate Covered Strawberry (which is AMAZING). The Lena Brewing Company have their own tap room, but they also have their products for sale at The Rafters! Connected to The Rafters is a great little gift shop where you can find lovely homeware items.


If you like murals, the junction of Main St and South Ave in Stockton has several pieces. They are located in the town, so you will have to turn off Hwy20 to see them!


🗺Apple River Fort State Historic Site, 311 E Myrtle St, Elizabeth, IL 61028, United States

Within the town of Elizabeth is the Apple River Fort State Historic Site. Close to the road is an interpretative centre with a small museum, but further along the track is the Apple River Fort. It was a reconstruction, built in 1996, after the foundations and artefacts were found after an archeological dig.

A similar fort was used during the Black Hawk War in the 1830’s. You can reach the fort at all times, however the interpretative centre has various opening hours (closed Monday & Tuesday during summer and only open on Fridays & Saturdays during the winter). Both are free to visit.

If you didn’t stop at The Rafters for food, a little further along is Cajun Jack’s Bar & Grill, a seafood and cocktail restaurant with a giant shark in the parking lot!

The Long Hollow Scenic Overlook is a small parking area just off HWY20, which looks across the Illinois landscape.


6 miles before reaching Galena’s Downtown, you’ll pass by Eagle Ridge Resort. This is a hotel, spa and golf course in Galena Territory. In summer nearby activities include: horse riding, zip lining at Long Hollow Canopy Tours, biking, hiking and hot air balloon rides. In the winter there is a Nordic Center with snowshoeing and ice skating. A popular event held at the Eagle Ridge Resort is the annual Great Galena Balloon Race.

If spirits are more your thing, rather than stopping at the Lena Brewing Company, Blaum Bros Distilling Co. have a cocktail bar and are a working distillery. For $10 per adult you can book onto a 45 minute guided tour of the distillery which includes a tasting session too.

Approximately 9 miles from Downtown Galena is my personal favourite, Chestnut Mountain Resort. During the summer they have various activities such as: Segway Tours, an alpine slide, mini golf and more! In the winter, they are a ski resort with 19 trails and a terrain park. Chestnut Mountain Resort also has it’s own hotel, check here for prices and availability.

Downtown Galena

Downtown Galena has many independent businesses and places to eat (my personal favourite is Gobbie’s Sports Pub and Eatery). If you enjoy tours, you can have a tour of former President Ulysses S. Grant’s home or take a ride of the Galena Trolley Tours.

You can find several different accommodation options for Galena Illinois on You can check different rates using the link below. There are several different chain hotels in Galena but if you are looking for something more unique, there’s: Chestnut Mountain Resort hotel, Cloran Mansion Bed & Breakfast, Irish Cottage Inn & Suites and Stoney Creek Inn to name a few!

Continuing along Hwy20 and crossing the Mississippi River, you will reach Dubuque, Iowa, which is also a nice stop for a day trip. If you are looking at extending your road trip along Hwy20, I covered some of the must see things to do between Dubuque and Waterloo IA: America’s Longest Highway: Awesome Events & Roadside Attractions Along Highway 20 in East Iowa!

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Chicago to Galena Road Trip Illinois USA

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