Saturday Night Plan

Question

Talk to be about Saturday evenings in the city. We’re arriving at 4pm ish. Taking the train from midway unless Ubers happen to be decent priced. Staying at the allegro. Hoping to head to the bean and navy pier as we only have the one evening for this trip.

I have some mobility issues and can walk shorter distances but need to make sure I don’t walk too much or I won’t be able to walk the next day.

We will have to make a few minutes from the train to our hotel and then to the train and to the bean. Would it be reasonable to expect to be able to uber up to the pier and then back to the hotel, or will traffic and Ubers be gridlocked and I should plan on the train only ? I don’t mind the train I just want to save my legs as much as possible, but with limited time don’t want to spend an hour in an uber either.

Two females, but We won’t be out super late or anything. Past 10 I was thinking I’d do an uber and not the train but open to advisement.

I’m hoping to squeeze in a quick dinner on the riverwalk but we will see. If anyone has any great suggestions for a CASUAL dinner that is gluten free I’m interested. Most places had no reservations left and while I saw some lovely Michelin star restaurants that won’t be what we are looking for this time ! I thought sitting on the riverwalk would be nice. Do you guys think there will be places I can just walk in and get seated on Saturday or is that nuts ?

Yes we only have this one evening this time. My friend wants to go see the Bean And I thought going to the skywheel would be a nice skyline view/experience the pier so we are pretty set on those two activities for this quick visit.

Also, I’m immunocompromised, do you expect to catch any issues if I wear my mask on the train and such ? I normally don’t have issues outside of where I live in WV, but just checking.

Answer

Arriving in Chicago around 4 PM on a Saturday gives you a tight window, but it is definitely possible to see both the Bean and Navy Pier without overexerting yourself, especially if you plan transportation carefully. Given your mobility considerations, minimizing walking is key.

Transportation Tips:

From Midway to the Allegro Hotel, an Uber or Lyft is a good choice. Traffic can be moderate on a Saturday afternoon, but the drive is generally 25-35 minutes depending on congestion. Trains would require multiple transfers and more walking, so a ride-share is preferable to save your legs.
For traveling to the Bean (Millennium Park) and Navy Pier, Ubers are workable. Saturday evenings can be busy, especially near Navy Pier, but early evening rides (before sunset) are usually manageable. You might experience a 5–10 minute wait, but it shouldn’t be extreme unless there is a large event.
Returning to the hotel late evening, an Uber or Lyft is recommended over walking or taking the train. Traffic tends to calm down past 10 PM, so ride-share wait times should be short.

Walking Considerations:

The Bean is within a short walking distance from the hotel if you are staying in the Loop, but you can also Uber there to conserve energy.
Navy Pier is about 1.5 miles from Millennium Park, so walking the full distance may be challenging. Consider Uber both ways, especially if you want to visit the SkyWheel and enjoy the pier without fatigue.

Dinner on the Riverwalk:

Casual spots with gluten-free options are available, but Saturday evenings are busy. Walking in without a reservation is possible if you are flexible about seating (bar seating or early/late dinner), but a short wait may occur. Arriving around 5:30–6 PM may increase your chances.
Good casual options along the Riverwalk with gluten-free menus include:

City Winery – offers casual American fare and gluten-free options.
Revolution Brewing (near Wabash & Riverwalk) – some gluten-free dishes.
Giordano’s (for gluten-free deep-dish pizza) – casual, but check wait times.

Activities:

The Bean (Cloud Gate) can be visited quickly, and early evening lighting is ideal for photos.
Navy Pier and the SkyWheel – plan for 45–60 minutes on the wheel for skyline views. You can enjoy the pier, grab a snack, and take photos without overexerting.

Health Considerations:

Wearing a mask in public transportation and crowded areas is sensible given your immunocompromised status. Most Chicagoans are accustomed to masks and there should be no issues with your choice.

Suggested Evening Plan:

Arrive at Allegro Hotel, check-in, and freshen up (around 4:30–5 PM).
Uber to Millennium Park for a quick visit to the Bean (allow 30–40 minutes).
Uber to Navy Pier for the SkyWheel and a casual stroll (around 6–7 PM).
Have dinner on the Riverwalk near your hotel (plan 7:30–8:30 PM, may need a short wait).
Uber back to hotel around 9:30–10 PM for rest.

This itinerary minimizes walking while allowing you to enjoy the key sights and a casual dinner. If anything feels rushed, prioritize either the Bean or Navy Pier, since both are highlights and can be visited quickly.