Chicago Trip June 2023

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Going to Chicago for 3 nights in early June for my niece's graduation. The graduation is at Wintrust Arena. The hotel right there (Mariott Marquis) is expensive as hell. From what I heard, I don't want to stay any further south than that. Any recommendations for reasonable hotel/Air BnB in a good area that's close to the El. We will be pushing a stoller with us, so don't want to walk a ton to catch an El, and won't be able to just call up an Uber without a carseat.

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Couple hotel options, while taking into account the stroller and not wanting to walk much:

- Magnificent Mile / River North offers a good location while you aren't tied up with graduation activities. Just want to check the distance from your hotel to Chicago or Grand Red Line stations. Most should be doable. Only consideration would be the half-mile walk from Cermak-Chinatown station to Wintrust.

- Green Line runs a couple blocks west of Wintrust, and will be half the distance as the Red Line. Definitely easier with a stroller. If you choose this route, you almost need to stay in The Loop. The only other option would be staying at The Hoxton, or something, in West Loop.

Again, I know you're trying to limit walking with a stroller. For a weekend visitor, I'd prefer to stay around River North / Magnificent Mile. Nice area to casually stroll through and make some stops for a break. Also, not far from Gold Coast - nice collection of restaurants and high-end shops.

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Also, send me your recommendations for some site seeing for a family with kids. Food recommendations. I've been to Chicago once, but it was for one night for a business meeting, and didn't have a lot of time to venture out much.

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Wife and I are in our early 30s and without kids, so I'm not sure how helpful I'll be on recommendations. Others on this board should be more help w/ kids, but for sightseeing, I'd check out Navy Pier, Architecture Boat Tour, Riverwalk, Lincoln Park Zoo, and Maggie Daley park. If you do LP Zoo, highly-recommend taking the family to Chicago Pizza and Oven Grinder Co. Been a couple times and always see families. Fun little experience.

I ended up booking the Fairfield Inn Downtown/River North. It's a block from the Red line Grand station. Had pretty good reviews, and was very reasonable for a Downtown hotel. Straight shot bus ride to Navy Pier as well.

Very nice

FYI the L does not run immediately to McCormick Place / Wintrust arena. It's perhaps ten minutes walk to the Green Line and fifteen to the Red Line. Metra Electric does run to McCormick Place but it's on a schedule, not short intervals like a subway train.

Stay literally anywhere in the loop or river north, it's easy access by taxi, L, or bike.

How old are your kids and what do they want to see? There are a lot of options. Maybe catch a game at Wrigley or hit the French Market under Ogilvie Station.

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Anyone ever done this tour?

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A lot of the stuff included in this tour are free so I'd hope the tour guide is good to make it worth the money.

Why no to the Sox? The pre and post game are not as good as Wrigley but the park offers a great Chicago food and beverage experience. Fantastic hot dogs/ polish sausage, cuban sandwiches and etc.

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I was thinking of doing a guided tour. Loop Tour

This is a 5.5 hr tour, but it includes a trip up to the Willis Tower Sky Deck, a trip to the Bean, and the boat tour on the Chicago River. Not a bad deal, and a good way to see almost everything in one day without worrying about coordinating and travel. Anyone ever done this tour?

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Personal preference, but you'll never get me on a 5.5 hour tour. That's a lot of time/patience - if I were a weekend visitor, would prefer to do your three listed sites on my own time. Don't want to be too presumptuous, but doesn't seem like you care a whole lot about seeing the inside of a few of those buildings in your link...?

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What are the general admission tickets to the Sky Deck like? Do I need to get there early to fight a line? How much time do they give you once you're up there?

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You can actually buy tickets for a specific time. As you could imagine, there will be lower availability around sunset.

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I've been to the restaurant at the top of the John Hancock Building before, but not 360/Tilt. Which is better?

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I've lived here 9.5 years and have yet to go to top of the Hancock Have done Willis several times - it's about a block from my office. I've gone without purchasing tickets in advance, but that's middle of the week at a weird time. Someone else may be able to tell you which is better.