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Ideas for 4 Day Road Trip from Chicago

New Delhi, India
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Ideas for 4 Day Road Trip from Chicago

Hi All,

There are 3 of us planning a 4 day return road trip from Chicago in late May. We would love to hear some ideas!

We'd like to take different routes to and from Chicago so we cover as many new places as possible. Here are things that would excite us:

- Scenic drives

- Something unique to do around the area

- Fun activities (casinos, water parks, hiking)

- A vibrant culture / night life in the places we spend our nights at

Ideally, we'd like to be on the road for no more than 4-6 hours in a day. We can leave early on Friday AM and be back Monday PM.

Looking forward to hear your inputs!


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1. Re: Ideas for 4 Day Road Trip from Chicago


Illinois City...
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2. Re: Ideas for 4 Day Road Trip from Chicago

Wisconsin Dells & nearby Devil's Lake, Wisconsin.

Both would certainly be big in the "fun activities" category, as well as being fairly unique and scenic (Devil's Lake is quite scenic.)

Chicago 'Burbs, IL
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3. Re: Ideas for 4 Day Road Trip from Chicago

You could do a loop from Chicago to Louisville travelling through Indianapolis (could stop there for a break, free art museum is great). Then from Louisville go to Cinncinnati and head back up or go to Lexington and then travel back through Cinncinnatti.

We went to Louisville and went to the Louisville Slugger factory tour and Churchill Down and some bourbon factory tours. In the Lexingon area we went to the Kentucky Horse Park and a tour of the Toyota Factory. We visited some local special food spots along the way and enjoyed the blue grass countryside. It was a nice relaxing trip.

Las Vegas, Nevada
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4. Re: Ideas for 4 Day Road Trip from Chicago

Millenium Park downtown, its a MUST! Wrigley Field, either catch a game or just go and hang out, wrigleyville neighborhood is amazing, you feel right at home! Michigan Ave.(magnificant mile) is lined with shops, walk up and down it, you will love it. Also hit up Navy Pier and the lakeshore. Beyond the, there are a few museums along lakeshore which are wonderful as well.

San Diego...
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5. Re: Ideas for 4 Day Road Trip from Chicago

If you're asking where you can stop on the way home from Chicago over a 4 day trip, it would help to know which direction you're heading. Going up to Wisconsin or into Michigan takes you to some very nice vacation destinations but may be too far out of your way. There's quite a difference between heading to New York and heading to Texas, for instance. Can we assume you'll have already spent some time in Chicago before returning home?

Or - are you asking about a 4 day trip where you leave Chicago on Friday morning and return to Chicago Monday afternoon? In that case I might suggest driving up to Mackinaw Island in Michigan, stopping in Saugatuck and maybe one more place on the way, then possibly quickly back through East Lansing (my old home town). I don't think you'd run into casinos or vibrant night life necessarily, but would find some beautiful drives, unique locations (like the dunes and the bridge) and great scenery and delightful small towns. Tons of outdoor activities.

Another possible trip would be through Milwaukee to Door County; Milwaukee would give you the night life and Door County the scenery; there's probably a casino somewhere around!

This section might help if you're looking for a 4 day getaway:


New York State, USA
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6. Re: Ideas for 4 Day Road Trip from Chicago

You can drive east to see Niagara Falls. Drive through Indiana to Ohio and continue along Lake Erie. You can stop in Toledo, Ohio where they have a terrific art museum. You might also stop in Cleveland, Ohio for the Rock and Roll Hall of Fame.

Both Niagara Falls, NY and Niagara Falls, Canada have casinos. There is more "action" on the Canadian side, however. You might need a Visa to travel there and back, while the US side has more natural beauty. The trip from Chicago to Niagara Falls is about 10 hours.

Chicago, Illinois
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7. Re: Ideas for 4 Day Road Trip from Chicago

Niagra Falls is no where near Chicago---it is a full 9 hour drive--I used to live near there and had another home in Chicago so I made the trip---a lot!!

Wisconsin Dells is very tacky, touristy stuff--wax museums--lots or waterparks and no where else to visit after the Dells. I would suggest driving to Galena, Illinois--pretty drive and very hilly and Galena is a nice quaint town about 3-4 hours from Chicago. There are not many great places to visit from Chicago unfortunately--I've lived here my whole life and our weekend trips are either Galena (3-4 hours west--as mentioned above---the Dells for waterparks and tackyness (3 1/2 hours north)--- New Buffalo, Michigan (about 1 1/2 hours Northeast) for quaint town and casino---Lake Geneva about 1 1/2 hours north for a summer getaway type town--restaurant and water activities.

New Delhi, India
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8. Re: Ideas for 4 Day Road Trip from Chicago

Thanks all for your suggestions - am looking up the places you've recommended and will build a trip around some of your suggestions.

@MGreene16: Yes - I'm talking about doing a Fri-Mon loop around Chicago so we start and finish in Chicago. In that sense, there's no particular direction we favor.

This is what the trip looks like for now: (need to revisit taking into account some of the suggestions here)

Day 1:

- Drive from Chicago to Wisconsin Dells; spend the day there at one of the 'touristy' water parks

Day 2:

- Drive from WD to Munising (National lakeshore park + kayaking in lake superior + biking trails)

Day 3:

- Drive to Petosky or Traverse City (looking for recommendations / suggestions on things to do here or other possible stops on the way to New Buffalo)

Day 4

- Drive to New Buffalo, MI

- New Buffalo activities: Four Winds Casino

- Drive to Chicago; 2.5 Hrs

Chicago, Illinois
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9. Re: Ideas for 4 Day Road Trip from Chicago

If this is your plan--here is more information:

A. Most people from Chicago will go to the following hotels at the Dells:

1. Wilderness

2. Kalahari

3. Great Wolf

B. I don't know of anyone in Chicago that goes to

Munising. It is pretty far and quite honestly, I don't even know what is up there. I'm sure some people go that far north into Wisconsin, but the more popular place is Eagle River.

C. There is an outlet mall on your way back to Chicago in Michigan City, Indiania called the Lighthouse premium outlet mall


it is a pretty popular outlet mall--if you feel like shopping.

The only other notes I have for you is if you are making the loop back to Chicago:

1. Your trip is alot of driving for 4 days

2. Forget about driving South or West of Chicago since you will see nothing.

3. You could drive East and go to Kings Island, Ohio and back and see some sights along the way.

4. If you don't want to loop around into Michigan you could:

a. Chicago to Galena, IL --Neat little town with a gambling boat right across the boarder in Iowa--STAY the night

b. Galena to Madison Wisconsin--Capital of Wisconsin--another cool bigger city--stop by on your way to the Dells or stay the night

c. Madison to Wisconsin Dells-Stay the night

d. Wisconsin Dells to Milwaukee Wisconsin-A stop or a stay

e. Milwaukee to Chicago

Chicago, Illinois
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10. Re: Ideas for 4 Day Road Trip from Chicago

I forgot to ask if you are a family or couples or singles.

In any event Galena is a sleep town---

Madison Wisconsin and Milwaukee you'll have culture and nightlife

If you've considered Lake Geneva which is about 1 1/2 hour from Chicago---it has a very vibrant nightlife--not much culture. Basically a Lake--summer home town with bars and restaurants and a younger crowd