2 night itinerary help

Question

Hi,

My husband and I (30s) are coming to town next month for 2 nights. Flying in and out of MDW. Plan on buying 3 day transit pass, and using public transport to get everywhere. We have become ballpark chasers and will be in town to see our TX Rangers against the White Sox. Staying at the Hyatt Regency, though I'm thinking of changing it to the Hyatt Centric Mag Mile - not sure, I actually stayed at the Regency over 10 years ago and remember not liking the location, too far east.

I'm concerned a little about safety, most of the places I want to eat aren't in the downtown area, would we be safe riding the el on evenings to Lincoln Park area for example and DePaul?

We're in town for whole Rangers series, though unsure if we will do a three games, definitely doing the Friday night game as its fireworks. Saturday is a 3pm day, they are giving out a cool shirt, Sunday is 1pm. We'd either do two games or all three, depending on how they are going, probable pitchers etc...

Main sights of interest for us other than baseball are, boat tour - I read May weather can be iffy though, this would be the end of May. Shedd Aquarium and Art of Institute.

Here's the rough plan so far;

Friday: Land 9am, take Orange Line to hotel. Shedd Aquarium and Alder Planetarium. Baseball at 6:40pm. Late night pizza at Pequods as open til 2am, again safe riding el back to hotel around midnight probably?

Sat: Possible Boat Tour - weather depending. Have previously done the CAF, was thinking of doing Wendalls. If do a 9am tour, have time to do something else before game possibly, Art Institute. Is that rushing too much, we usually spend about 1hr30-2hrs at art museums. 3:10pm Baseball. Somewhere downtown for Tavern style pizza. Navy Pier have 10pm fireworks worth seeing? I love firework shows.

Sun: Lincoln Park day, visit the Zoo and Conservatory. Late lunch/early dinner at Chicago Pizza & Grinder Co. Flight at 8pm out of MDW.

Other sights of interest are: Cultural Centre, Garfield Conservatory - I think this is too far out for us to get to, and the Federal Money Museum only open on the Friday.

I'm also concerned we are eating too much pizza, but they are all different styles of pizzas and that what we want to eat!

Thoughts, opinions, critic please

Answer

Your two-night itinerary looks like an exciting mix of baseball, sightseeing, and good food, and you're hitting some great spots around Chicago! Let’s go through your plan and offer some feedback and suggestions to help you make the most of your short trip. I’ll also address your concerns about safety and transit options.

1. Hotel: Hyatt Regency vs Hyatt Centric Mag Mile

The Hyatt Centric on Michigan Avenue is a more central location, with easy access to shopping, restaurants, and attractions like the Art Institute and Millennium Park. It’s closer to the “touristy” part of the city, but keep in mind it’s also a busier area. The Hyatt Regency is in a slightly quieter area, but still within walking distance to major attractions. Both are great, but if you want to be closer to the action, the Hyatt Centric is the better option for your short stay.

2. Safety and Riding the "L" (El) to Lincoln Park

Chicago’s public transit system, including the “L” (El) trains, is generally safe, especially during the day and early evening. For your late-night return after dinner or a game, the trains can get quieter, but most stations, especially those near tourist areas like downtown and Lincoln Park, are well-lit and have a steady stream of riders. Just be mindful of your surroundings, and if you're concerned, you can always opt for a ride-sharing service like Uber or Lyft for a more comfortable and direct route back to your hotel.

3. Friday:

Your arrival day looks solid. Shedd Aquarium and Adler Planetarium are both great choices for your first day. Both are located near the Museum Campus and will give you a nice overview of Chicago's lakefront. With the 6:40pm game, it's realistic to do a boat tour in the morning. However, if the weather isn't great, you might consider skipping the boat tour and exploring more of the museum campus or the nearby parks. As for late-night pizza at Pequod’s, that's a fun, casual choice. Just be prepared for a possible 30-minute to 1-hour wait, as it’s a popular spot. After the game, riding the "L" back should be fine, but it's always best to stay alert late at night.

4. Saturday:

The boat tour in the morning sounds great. Wendella’s tours are fantastic, but if the weather is poor, consider postponing the tour for your next visit and checking out the Art Institute or another museum. The Art Institute will take about 1.5 to 2 hours to explore, but if you’re trying to squeeze it in before the game, I’d recommend either doing a quick visit or saving it for the end of the day. After your 3:10pm game, Tavern-style pizza is a must in Chicago. A good recommendation for this is Bartoli’s Pizzeria, which serves classic Chicago-style thin crust pizza. As for Navy Pier’s 10pm fireworks, they’re a fun show, but if you’ve seen other fireworks shows, it might not be as impressive as some of the larger ones in other cities. Still, it’s a nice way to end your day if you’re nearby.

5. Sunday:

Lincoln Park is a great place to visit, especially with the zoo and conservatory. Both are free and open to the public, making it an easy choice for a laid-back morning. Chicago Pizza & Grinder Co. is a good spot for another pizza experience, though it’s a bit different from the deep-dish styles you’ll have experienced on the previous nights. If you're craving something a little different, you could also try a "Chicago-style hot dog" for a fun local twist. With your 8pm flight, you’ll have plenty of time to wrap up the day and head to MDW.

6. Other Sights of Interest:

Cultural Center: The Chicago Cultural Center is a beautiful, historic building with free art exhibits and performances. It’s a short walk from Millennium Park and would be an easy addition to your downtown itinerary if you find time after the Art Institute or before the game.
Garfield Park Conservatory: This might be a bit far for your short visit, as it’s on the west side of the city. Given the time constraints, it’s probably best to save it for another trip.
Federal Money Museum: As this museum is only open on Friday, you could consider squeezing it in if it’s a priority. However, I’d suggest focusing on your more central activities unless you’re really interested in learning about the U.S. Mint and coin collection.

7. Concerns about Eating Too Much Pizza:

I totally get your concern about eating too much pizza! But given that Chicago pizza styles are so different (deep-dish, thin crust, tavern-style, etc.), you’re really sampling a variety of different types of food. If you feel like you’ve had enough pizza by Sunday, you could always switch it up and grab something lighter, like a salad or sandwich, or explore Chicago’s other food scene with a local favorite like a Chicago-style hot dog or a hearty bowl of chili.

Final Thoughts:

Your itinerary is packed but doable, and I think you’ll enjoy your time in Chicago. I’d recommend staying flexible with the boat tour and Art Institute based on the weather and how much time you have between activities. Since you love fireworks, the Navy Pier show could be a fun end to your Saturday. If you feel rushed, don’t hesitate to skip some items to avoid feeling overwhelmed, but I think you’ve created a great mix of iconic attractions and experiences.

Enjoy your trip, and have a fantastic time cheering on the Rangers!