3 day visit for Cubs, etc

Question

Our primary reason for visiting was to see the Cubs at Wrigley, but we enjoyed many other things during our short stay.

Our hotel was the Hilton Downtown/Magnificent Mile (directly across from the Hancock bldg/360 Chicago). I got a great corporate rate, possibly because there is some construction in the building (it did not bother us at all). The location was good, although I’d love to have been closer to a train station (it was a 15-20 min walk to the red or blue line).

We took the blue line from O’hare to the Lake/Clark station (super easy, bought $5 day passes from the kiosk). According to Uber it would’ve been over an hour drive due to traffic, so the train saved us some time (it’s fun to whizz past the gridlock). We then got an uber from the station to the hotel, which took almost 20 minutes to go 1.4 miles. It would’ve been faster to walk but we didn’t want to schlep our carryons.

After check-in we strolled the lively Michigan Ave down to Millennium park, took the obligatory Bean photos, and enjoyed the lovely 75* weather. We then made our way to the Art Institute, which stays open until 8 pm on Thursdays. It was free to locals this evening (I believe every Thursday evening in summer?) but crowds were not overwhelming. We spent several hours here, so many famous works to enjoy.

Dinner was at Lou Malnati’s, right off Michigan Ave, a short walk from the museum. We had a really good Caesar salad and the “Chicago classic” deep dish. We are officially a tourist cliche, no regrets though. Fun atmosphere and good pizza.

Answer

It sounds like your 3-day visit to Chicago was a great mix of iconic sightseeing, local culture, and baseball excitement. Staying at the Hilton Downtown on the Magnificent Mile is convenient for walking to many attractions, although being a bit farther from the train can add a short commute. Buying $5 day passes for the CTA is a smart move for flexibility and saving time versus navigating traffic from O’Hare.

Here’s a breakdown of your first day and tips for maximizing similar short visits:

Arrival & Transportation: Taking the Blue Line from O’Hare to Lake/Clark station is efficient, fun, and much faster than driving during peak traffic. A short Uber or taxi ride from the station to your hotel is convenient if you have luggage.
Michigan Avenue & Millennium Park: Walking down Michigan Avenue gives you a taste of the city’s energy. Millennium Park is a must-see for photos with “The Bean” and nearby attractions like Crown Fountain.
Art Institute: The Thursday evening extended hours are perfect for tourists looking to avoid daytime crowds. Planning several hours here allows you to see major works without feeling rushed.
Dinner: Lou Malnati’s is iconic for Chicago deep-dish pizza and a classic tourist experience. Caesar salad and the Chicago classic pizza are great choices for first-time visitors wanting the full local flavor.

Additional suggestions for a 3-day visit focusing on Cubs games and other attractions:

Consider catching a Cubs game at Wrigley Field if schedule allows—walking around Wrigleyville before or after the game is lively and fun.
Other key attractions within walking distance or a short train ride include the Skydeck at Willis Tower, Navy Pier, and the Magnificent Mile shopping district.
If you like museums, the Field Museum or Museum of Science and Industry can be excellent daytime activities, especially with kids or family members who enjoy interactive exhibits.

Tips for transportation & efficiency:

Use CTA day passes for unlimited travel on trains and buses—it’s cheaper and avoids traffic delays.
Walking is often faster for short downtown distances, especially during rush hours or when Uber/Lyft wait times are long.
Plan meals near attractions to reduce travel time, like you did with Lou Malnati’s near the Art Institute.

Overall, your approach of mixing cultural visits, walking around downtown, and ending the day with classic Chicago cuisine makes for a balanced, memorable 3-day trip.

3 day visit for Cubs, etc

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