5 Easy Weekend & Day Trips From Chicago

Easy trips from Chicago - Road Trip

Are you looking for an easy and affordable way to explore other sights and cities near Chicago? Exploring more cities while on vacation doesn’t have to be a hassle. These are the 5 easy weekend & day trips from Chicago which can be combined with your visit.

Taking short flights or car trips to nearby destinations like Detroit and Canada is easier than you think. Combining your trips can save you money and help you see more. Whether it’s a day trip to the nearby suburb or a few days in another state or country, you can find the perfect side trip for you.

These Easy trips from Chicago guide will give you the best of both worlds – convenience and affordability. Start planning your visit to Chicago and decide where else you want to see while here.

Read the full Chicago destination guide on how to visit Chicago like a local HERE.

In this Chicago destination guide I share the top places to see, my favorite hidden gems and tips to best navigate the iconic windy city.

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Plan Your Visit






5 Easy Weekend & Day Trips From Chicago – Ideas


Easy trips from Chicago - Canada

Hitting up another country from Chicago is also very doable as Canada is our neighbour and Toronto and Niagara Falls are just a short day drive away.

See what I got myself into in Canada here.

Car Ride From Chicago (to Toronto) – 8 hours and 30 minutes

Flight Time From Chicago (to Toronto) – 1 hour and 40 minutes


Easy trips from Chicago - Detroit

The “Big D” as many call Detroit is a hub for art and the music scene, which makes this a great road trip from Chicago. Try a Coney dog, visit the historic Motown Museum and don’t miss the Detroit Institute of Arts, during your stay.

See the top highlights to see HERE.

Car Ride From Chicago – 4 hours

Flight Time From Chicago – 1 hour


Easy trips from Chicago

If you are looking for nature; the state of Wisconsin is calling your name.

  • Wisconsin Dells in particular is a fantastic weekend getaway for families. Activities include water-park, theme parks and places for camping. The peak season to visit is in the summer but there is winter activities available in the winter.
  • Milwaukee is a good day trip option for wine, cheese curds and city sights.

Check out the best tours in Wisconsin HERE.

If you like beer, don’t miss trying “New Glarus” beer as it can only be found in Wisconsin. Be sure to pair it with cheese as this is what Wisconsin is known for.

Car Ride From Chicago – 1 hour and 30 minutes

Starved Rock National Park

Easy trips from Chicago

The perfect place for hikes outside of the city. Make a day out of it and check out some of the wine shops around the state park and for those under 21, there is a cute candy and cupcake store in the town closest to the park.

Car Ride From Chicago – 2 hours

Swallow Cliff Woods

Easy trips from Chicago - Swallow Cliff Woods

Keen for a workout with spectacular scenery? Then Swallow Cliff Stairs in Palos Park is just for you. These stairs are a no joke workout.

Car Ride From Chicago – 30 to 40 minutes depending on traffic.

Cheap flights with cashback

Final Note

Don’t get me wrong, there is plenty to see in Chicago. Only plan on visiting Chicago or want to explore more of what Chi city has to offer, then find my full Chicago destination guide HERE.

Plan your visit from A to B with local recommendations from an expert traveler. It’s getting the best of both worlds for your ultimate visit.

My visiting Chicago like a local destination guide includes:

  • What to do
  • Where to stay
  • How to get around the city
  • Where and what to eat
  • Where to party
  • And what to see

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