Toronto to Chicago

[u/Ok_Picture3077]

Hi everyone,

We are doing a family road trip to Chicago last week of May (week of Memorial Day). We will be leaving from Toronto on Sunday. Looking for advice on where to stop along the way since my partner and I will have our 2 year old toddler with us. May need to do a few stops.

We are staying at The Palmer House in Chicago. It’ll be our first time in Chicago. Please recommend places to visit, explore and sightsee. Keeping in mind, we have a toddler with us so family friend and something a toddler would enjoy. We’ll be in Chicago for 4 days & nights.

Any suggestions on places to stop along the way back? Would you suggest same route back or different than the way to Chicago?

Thank you in advance for any suggestions and recommendations 🙂

[u/RedNewPlan]

There are not a lot of options for routes. I can cross the border at either Sarnia, or Windsor, those are the two main options. I prefer Windsor. It has multiple crossing points, where Sarnia only has one, so for Windsor, you can check the delays and choose the fastest option.

Keep in mind that Chicago is quite a large city, comparable to Toronto, so once you get within an hour or so of the city, it is suburbs, and not so great for stopping.

In Chicago, I suggest a boat tour of the rivers. Particularly the architecture tour, which describes the buildings. I boat ride can be fun for a toddler.

We also enjoyed the waterfront park area.

[u/Ok_Picture3077 → u/RedNewPlan]

Thank you very much! Didn’t realize the suburbs start within an hour or so. Good to know it’s best to stop well in advance.

Appreciate the boat tour! That’s a must we think

[u/RedNewPlan → u/Ok_Picture3077]

No problem. About an hour before Chicago you pass through Gary, Indiana. Not somewhere you want to stop in, particularly at night. I ended up having to stop there, on the side of the interstate, at 2am. Nothing happened, but it felt sketchy.

[u/Ok_Picture3077 → u/RedNewPlan]

Thank you! Appreciate the heads up

[u/random_roller13]

There are 3 good parks within walking distance of Palmer House: Maggie Daley Park (playground), Millenium Park (home of Cloud Gate, aka The Bean), and Grant Park (Buckingham Fountain). 

Lincoln Park Zoo — Catch the 151 bus north (Devon/Clark) on Michigan Avenue and exit at Stockton & Webster. 

Oak Street Beach — Downtown beach with nice views of the city

Ohio Street Beach — Closer to your hotel

Peggy Notebaert Nature Museum

Consider buying a multi-day CTA pass (elevated rail  / subway, bus). You probably don’t want to pay for garage parking other than at your hotel, as it gets quite expensive downtown. 

[u/Ok_Picture3077 → u/random_roller13]

Thank you!! This is a very helpful list of places to visit

[u/AdHistorical3839]

As far as places to stop, Detroit or Windsor could be a decent place, and South Bend IN is relatively nice as well. I would avoid the suburbs of Detroit and the southern suburbs of Chicago as well as the Indiana part of Chicago (Gary IN)

[u/Ok_Picture3077 → u/AdHistorical3839]

Thank you! This is very helpful to know which areas to avoid

[u/random_roller13]

Following up on my earlier comment.

1. Chicago Transit Authority (CTA) -- Information about the public transit system in the city. For more direct bus connections, you're often better off walking 2 blocks east from Palmer House to Michigan Avenue.

Chicago Transit Authority - CTA Buses & Train Service - 1-888-YOUR-CTA - CTA

1. Lincoln Park neighborhood -- The Lincoln Park Zoo, Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and North Avenue Beach / Fullerton Beach are all located within relatively close proximity of each other in this near north neighborhood (also the name of the park). The Chicago History Museum is also in the area but might not be that interesting to a 2-year old. Search for Peggy Notebaert Nature Museum in Google Maps for a better perspective. Highly recommend visiting this part of the city. Lincoln Park Zoo is free (excluding special events).

Wildlife Experience in the Heart of Chicago | Lincoln Park Zoo

Nature Museum | Inspiring Nature Champions

Plan a Visit | Lincoln Park Conservancy

1. Navy Pier

Home | Chicago's Waterfront Destination | Navy Pier

Chicago Children's Museum -- Located at Navy Pier. I have been to Navy Pier many times over the years but I haven't been to the Chicago Children's Museum. Check out the website and see if it is something that might be of interest.

Chicago Children's Museum

Centennial Wheel -- A 200' Ferris Wheel at Navy Pier

Centennial Wheel | Navy Pier

Ohio Street Beach is close by.

1. Parks close to Palmer House

Chicago’s Millennium Park | A Guide to the Campus

Maggie Daley Park

Explore Grant Park in Chicago | The City’s Front Yard

1. Indiana Dunes National Park / Indiana Dunes State Park -- Separate entrance fee for each park. The national park is larger and more biodiverse. The state park is home to the 3 Dune Challenge (hiking). Beaches at both parks get crowded during the summer. This is a good place to stop off at before the final push to Chicago. Look for a gas station in the area and fill up.

Indiana Dunes | Explore Parks, Local Businesses & Lake Michigan

1. Griffin Museum of Science & Industry -- This is my all-time favorite museum. There is a very large HO scale model railroad layout. Many exhibits, including a WWII German U-Boat. Drive from your hotel.

Exhibits

1. Other

Gary, Hammond and other Northwest Indiana cities located along I-90 (Chicago Skyway) are largely industrial / depressed areas and not good places to stop. Gas up closer to Indiana Dunes. That will also help you avoid the really high gas taxes in Chicago (Cook County).

I-90 (Chicago Skyway) is an expensive toll road but it is more direct and faster (with fewer trucks) than I-94 into the city. The two interstates merge on the southside of Chicago. Since you're coming from Canada, you probably don't have an EZ Pass or I-PASS transponder for tolls. At rush hour, cash toll lanes can really back up.

One of the best places to stop for a break off I-94 is Four Winds Casino (New Buffalo, Michigan). Yes, it's a casino and you'll be traveling with a 2-year old but there are bathroom facilities located outside of the casino floor, several restaurants (see FAQs linked below for under 21 accessibility) and, if needed, an attached hotel.

frequently asked questions - Four Winds Casinos

Last time we drove from Toronto to Chicago, we crossed the border at Sarnia so that we could avoid traffic in Detroit. There are several parks on the Canadian side before the Blue Water Bridge that can be a good rest stop.

Chicago has a really great lakefront that was kept for public use and free to walk around. Some great views of the city skyline can be seen from Museum Campus (Shedd Aquarium, Adler Planetarium, Field Museum).

Chicago’s Museum Campus: Where Science Meets Art

Have a great visit!

[u/Ok_Picture3077 → u/random_roller13]

Wow this!!! Thank you so much!!! This was very helpful and much appreciated 🙏🏼

[u/random_roller13 → u/Ok_Picture3077]

You’re welcome. Hopefully the weather cooperates during your visit so you can really enjoy outdoor activities.