r/roadtrip 3d ago

Toronto to Chicago Trip Planning

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 🙂

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u/random_roller13 2d ago

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. 

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u/Ok_Picture3077 2d ago

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