Road Trip to Chicago from Toronto – Four Day Itinerary

You’re going on a road trip to Chicago from Toronto? …. You should always takes the Detroit-Windsor tunnel over the Ambassador’s Bridge

…were the first word’s that my friend, and fellow SYDE classmate uttered as soon as I casually mentioned that I was going to go on a road trip to Chicago from Toronto.  According to his co-workers who regularly traverse the Detroit-Windsor border, the tunnel is hands down better than the Ambassador’s Bridge. The line is shorter, it is cheaper than the bridge, and the border checkpoints are faster.

So far, I’ve been really lucky that with each destination I go, someone I know either knows another person who has made the same trip before, or has done the trip themselves as well. Regardless of the situation, I’ve always received warm words of advice that has made each vacation smoother and more enjoyable. Any advice to get to our destination a little faster was much appreicated – especially since driving from Toronto to Chicago is already an 850km  (~530 mi) journey one way.

Kent was off in Vancouver during the same week I decided to go to Chicago and Anson was well… doing whatever he does best in Seattle (most likely climbing mountains) so this road trip was another SYDE Dash from the main group again.

This was an aggressively planned “see as much of Chicago in four days while breaking Maria’s 2 hour driving limit threshold”.

Chicago Attractions


B&W image of pedestrians walking to the Navy Pier in Chicago
Pedestrians Walking to the Navy Pier
PC: Angelo Manalac

It is my strong belief that one city (let alone a country!) cannot be fully appreciated without at least spending a week’s time there. But alas, not everyone is blessed with unlimited vacation days so anything shorter requires us to prioritize and set a theme for each trip. In this case, my boyfriend, Angelo, has never been to Chicago – so hitting as many of the top tourist spots was a priority.

This four day road trip itinerary from Toronto to Chicago consists of the following attractions Chicago has to offer:

  • Turtle Racing at Big Joe’s
  • Magnificent Mile
  • Millennium Park
    • Cloud Gate / The “Bean”
    • Jay Pritzker Pavilion
    • Lurie Garden
    • Wrigley Square
  • Grant Park
    • Maggie Daley Park’s Play Garden
    • Buckingham Fountain
    • The Art Institute of Chicago
    • Museum Campus
      • Field Museum of Natural History
      • Shedd Aquarium
  • Navy Pier
    • River Architecture Tour
  • Willis/Sears Tower
  • The Signature Lounge at the 96th (in lieu of 360 Chicago Observatory Deck / John Hancok Observatory – same building just a different floor!)

Four Day Itinerary: Toronto to Chicago and Back

Day One – Windsor, Lou Malnati’s Deep Dish Pizza, and Big Joe’s Turtle Racing

  • 6:00 AM – Leave Toronto
  • 9:30 AM – Stop in Windsor to eat at A Dog’s Breakfast
  • 12:00 PM – Find the Detroit-Windsor Tunnel and cross the border.
  • 5:30 PM – Arrive in Chicago!
    • We checked in at the Ohio House Motel and ordered delivery from Lou Malnati’s
  • 8:30pm – Take an Uber to Big Joe’s to watch some Turtle Racing (note: Turtle Racing only happens on Fridays so plan accordingly!)
  • 12:30am – That’s a wrap for day one in Chicago

****Maria’s Tip – Weekday Vacation Start? Leave at 6:00 AM from Toronto to Avoid Rush Hour in Toronto, Windsor, Detroit, and Chicago! SUPER WIN****

Our first day of the trip began on a Friday. My friend recommended that we start at 6:00AM to avoid conflicts with rush hour traffic times.

By leaving at 6:00 AM, you are able to leave before most of the working commuters heading into Toronto make their way onto the highways. From personal experience, the Toronto morning commuter rush starts at 7:00 AM and doesn’t end until well past 9:30 AM.

By 9:30 AM, we had arrived in Windsor, where it was recommended we take a quick breakfast break to avoid the tail-end of the cross-border morning commute. Similar to the Toronto morning commute, the cross-border traffic peaks from 7:00 AM and lasts until 10:00 AM.

Then as an added bonus, the distance from Detroit to Chicago is about 4.5 hours, and even if you take a couple of bathroom pit stops, you should arrive into the core of Chicago no later than 4:30 PM – before the congestion from the evening commuter rush really picks up – leaving you with enough time to relax for the evening with still enough time to explore parts of the city before calling it a night. Because we got lost and lost time, we  ended up arriving in Chicago at 5:30 PM instead – hitting congestion head on.

Day One Details

****Maria’s Tip – If you aren’t comfortable driving long distances but want to expand your experience, offer to drive more familiar roads first – like…. driving on the Canadian side instead of the American side****

I doubled my 2 hour driving threshold! I can now drive for FOUR HOURS without quitting. As someone who doesn’t drive much beyond the weekend trips to the grocery store, this is a monumental step for me. Sure, my butt was sore, but I did it.

  • 24 hours before our trip, our AirBnB host cancelled on us, so Ohio House Motel wasn’t actually our first pick but it worked out
  • We got lost trying to find the Detroit-Windsor tunnel, and our conversation with the border control officer was longer than usual (upcoming blog post!).
  • We loved the Turtle Racing experience so much I think it deserves its own post(upcoming blog post!)! Our favorite experience in Chicago by far.

Day Two – Exploring Millennium Park, Grant Park, Navy Pier, and Cruising with the River Architecture Tour

  • 10:00 AM – Good morning! Let’s wake up, find breakfast, and shower!
  • 12:00 PM – Walk to the Millennium Park then head across to Maggie Daley’s Play Garden located just North of the Millennium Park
  • 2:00 PM – Walk to Buckingham Fountain
  • 3:00 PM – Eat at Halal Guys
  • 4:00 PM – Arrive at the Navy Pier and purchase tickets for River Architecture Tour (6:30 PM)
  • 8:50 PM – Deep Dish Pizza at Giordano’s Pizza
  • 10:00 PM – Arrive at John Hancock Tower and purchase CityPass
  • 10:30 PM – Signature Lounge (views + drinks)
  • 12:00am – That’s a wrap for Day Two in Chicago!

Day Two Details

This day was so jam-packed with activities that we saved the details for a separate blog post here.

Read it here on “Road Trip to Chicago Day TWO – Around Millennium Park

The river cruise was such a hit with the two of us, that we really want to go into more detail for that as well – stay tuned for another blog post on that as well!

Day Three – CityPASS Tourist: Art Institute of Chicago, Shedd Aquarium, Buckingham Fountain (again!), and Willis Tower

Dragon and Lion Silk Panels at the Art Institute of Chicago
Angelo posing in front of the Dragon and Lion Silk Panels at the Art Institute of Chicago
  • 10:30 AM – Rise and Shine! We woke up and ate the remains from last night’s for breakfast
  • 11:30 AM – Art Institute of Chicago
  • 2:50 PM – Shake Shack
  • 3:30 PM – Shedd Aquarium
  • 5:00 PM – Buckingham Fountain (the water was finally on!)
  • 7:00 PM – Willis Tower
  • 8:30 PM – Head back to motel for a quick rest
  • 9:30 PM – Trader Joe’s and Portillo’s Hot Dogs
  • 10:00 PM – Motel rest for HG TV Marathon
  • 11:30pm – Goodnight world! Sleeping earlier since we need to wake up early the next day

Day Three Details

This day was so jam-packed with activities that we’ll save the details for another blog post!

Day Four – Straggler CityPass Tourist

Maria with Sue, the T-Rex
  • 7:00 AM – Wake up and eat breakfast at Eggsperience
  • 8:00 AM – Head back to motel and clean up / shower
  • 9:00 AM – Drive to Field Museum (paid for parking $$$$)
  • 12:00 PM – Drive back to Toronto
  • 10:00 PM –  Arrive home

Day Four Details

The last day was mostly the drive back home to Toronto. But we only visited three of the seven options from the CityPass! So we decided to extend our stay in Chicago by touring one more location after we checked out from our motel.

The drive to the Field Museum was short and sweet, but the parking on the other hand, was not.  For three hours, parking was $19 at the Field Museum! Like most cities, parking fees can really make a dent to your wallet if you aren’t careful.

****Maria’s Tip – Any downtown exploration should really be done without a car! Parking Fees will suck your budget faster than you can blink an eye.****

The CityPASS version of the Field Museum ticket offers access to all of the Field’s Museum exhibits including the Underground Adventure – an interactive exhibit meant for children, to explore all the activities that go on directly underground.  We stayed here for three hours and we only had time to see the following exhibits in short detail:

  • Sue the T-Rex
  • Tattoo exhibit (ticketed but covered with CityPASS)
  • Underground Adventure (ticketed but covered with CityPASS)
  • Travelling the Pacific
  • Ancient Egypt
  • Galapagos 3D Movie (ticketed but covered with CityPASS)

Although some travel blogs recommend to spend an hour or two here, Angelo and I agreed that we could have easily spent more than the three hours we were here for – especially when there’s a 3D movie involved that took 40 minutes of our time. Don’t get me wrong though! The movie was a great documentary and makes me want to re-binge watch Planet Earth and Planet Earth II again.

For future visitors who enjoy museums, we definitely recommend spending a day here if you have the chance!

The drive back home was surprisingly quick – 8.5 hours as predicted by Google Maps, even with the occasional restroom breaks and driver switching breaks. From our drive in to Chicago, we learned that 3 hour driving shifts were best to give our legs a good stretch and give each other more time to rest and recharge on the passenger’s side. Those cat naps and shorter switches made for a safer and more pleasant ride back home.


Angelo and I touring the Field Museum on our last day in Chicago. Aching feet and low energy didn’t stop us from persevering and enjoying our time!

Looking back, we had an aggressive itinerary. To save money and boost our health – we decided to walk to almost every destination we could (excluding going to Big Joe’s as it was half an hour’s drive away from the core area of Chicago)

By the end of the trip, we each walked over 32 km (~20 mi) in the span of three days. My feet ache just thinking about it.

If you were to follow our itinerary, I would recommend you take public transportation, the taxi, or the Chicago go bus to get around. It will not only give you more time at each destination, but will also save you from aching feet too!

Cheers to another successful road trip!

Angelo and Maria at the Buckingham Fountain in Chicago

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