Visiting Chicago - need advice

On Wednesday I am flying to Chicago and I will be there through the 28th. My sister and 2 of her colleagues are attending the ALA Conference and I am tagging along and sight seeing while they are in conference.

Looking at the weather apps, it looks like mid-70s to mid-80s, with chances of rain and lots of clouds. I am in very hot, very dry Sacramento, so this humidity is likely to kill me, right? I have no idea what clothes to pack. Will I be sweltering in jeans? Is it like a layering thing where I should have like 5 layers and plan to discard them as the day goes on? Is it really super windy in Chicago this time of year? I mean, I know it’s called The Windy City and all. This will be my first time visiting the Midwest and I just don’t know what to expect.

Also, as long as I’ve got your attention, I am on my own for dinner Friday evening. Any suggestions? Anyone in the area want to meet for dinner somewhere?

Saturday or Sunday I am planning to tour Wrigley Field, probably Saturday. The Cubs are not in town or I’d be taking in a game.

Everybody else will be dressed in shorts and short-sleeved shirts (or the dress/skirt equivalents) unless your job puts you in pants. It won’t be uncomfortably warm and the lake tends to cool things down a bit as well – “cooler by the lake” is a standard weatherman statement around here. Usually humidity is only an issue when it’s super warm. Thursday, if it’s actually scratching 90, you might notice it if it’s muggy but the days in the 70s you won’t. No excessive wind, while it does get windy the “Windy City” moniker is supposedly more about talky politicians than weather.

It doesn’t look as though the weather ever drops below the high 60s and that’s at 3am so you shouldn’t even need a light jacket. Maybe a long-sleeved top for the hotel room if the AC won’t turn off :wink:

Thanks for the tips. I am glad to hear that it likely won’t be as humid as I feared. I’m really looking forward to this trip, but wasn’t sure about weather and packing. Trying not to over pack.

It looks like it’s going to be fairly humid on Thursday and Friday: dewpoints in the 60s, which will probably feel kind of tropical to you, based on coming from a drier area. It shouldn’t be quite as humid on Wednesday, or over the weekend.

Downtown Chicago is full of tourists at this time of year (I work across the street from the Art Institute, and it’s definitely the “busy season” here on Michigan Avenue); you’ll see short-sleeves and shorts everywhere.

As far as restaurant recommendations: do you know where your hotel is (or the area you’ll be in on Friday afternoon)? Is there a particular type of food in which you’re interested (or would like to avoid)?

Also, I should note that the Pride Parade is on Sunday. It won’t affect downtown much (if at all), but the neighborhood where it occurs (which isn’t too far from Wrigley Field) will be extremely crowded on Sunday. If nothing else, it suggests that, if you have a choice, go for your Wrigley tour on Saturday.

Exactly, unless you’re attending the Pride Parade, you don’t want to be anywhere near it. Traffic will be snarled in all directions, and the Red and Brown lines will be packed. That’s the reason the Cubs never have a home game on that day, the parade attracts up to one million spectators.

It’s called the Windy City because of the loud mouth politicians talking up the city after the Chicago Fire, nothing to do with the weather.

Where are you looking for dinner options, I live near Wrigley Field and can certainly give plenty of options in this area.

The weather is actually quite mild for this time of year, last week was brutal heat and humidity. You’ll be fine in whatever summer clothes you would wear in California.

We are at the Hyatt Regency downtown. I’m sure there is a ton of spectacular restaurants. We love pretty much all kinds of food, but maybe not seafood as much as other things.

Thanks for the tip about the Pride Parade. I’ll opt for Wrigley on Saturday then.

Gotcha! You’re not too far from Navy Pier, which is, essentially, a very long tourist trap. There are some neat things there, including a large Ferris wheel, but it’ll likely be very busy (and expensive)…so, unless it’s your desire to be stereotypically touristy, it’s probably something to avoid.

If you’re interested in trying one of Chicago’s signatures – deep dish pizza – you’re pretty close to Pizzeria Uno and Pizzeria Due, where it was developed. (Two different locations, a block apart, but owned by the same people, with an identical menu.)

Little Three Happiness Forum is a great Chicago food resource:

LTH Eating out in Chicagoland

LTH Great Neighborhood Restaurants

Also, Groupon is based in Chicago, so you can often find deals for restaurants and attractions on there. The above mentioned Pizzeria Due has one, for example.
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There’s a great German restaurant within a few blocks of the Art Institute (as seen in Ferris Bueller’s Day Off for frame of reference) and’The Bean’ (real name Cloud Gate).
When I’ve needed to kill time in Chicago I get on one of the El routes and take it to the end, then hop back on and go back facing the other direction. Simple sightseeing!

For visitors, I often recommend this circle trip: Brown Line L to Belmont; transfer across the platform to Red Line to Berwyn. Downstairs, board the 146 bus, which will run along Lake Shore Drive to bring you back to the Magnificent Mile and State Street. Should be about 90 minutes all told.

You mentioned dining alone. If you don’t manage to dig up a companion, I recommend a restaurant called Carmine’s. It’s on Rush Street in the Viagra Triangle*. If you go downstairs and sit at the big, horse-shoe shaped bar, you are immediate looped into a big circle of locals, business travelers, and vacationers and everyone is very friendly. You can order the full menu while seated there listening to the piano player. It is awesome Italian food, with one drawback: five or six days later, you are hungry again! Even if you DO have a companion, it is a great place for old school Italian food.

*named for the triangle formed by Rush and State Streets where gold-digging young chicks hook up with wealthy old men.

Whatever you do, do NOT miss that Wrigley tour. It’s honestly the most amazing baseball-related thing I’ve ever done in my life.

I would highly, highly recommend the architectural boat tour if you want a good overview of the city and its architecture. It’s a great vantage point to see the city, and it is very informative. I went on one twenty years ago, not expecting much, but wanted something fun and “touristy” to do with an out-of-country guest, and I was impressed by it. I’m a born-and-raised Chicagoan, and it was worth every penny to me.

That architecture foundation also has walking and bus tours if you browse the page, but that boat tour just sticks out to me as a wonderful experience, for tourists and locals alike.

As for restaurants, if you want to stay within walking distance of your hotel, The Gage on Michigan Ave is about a ten minute walk away, with what I would describe as a gastropub atmosphere and cuisine. You can find their menu online. Also, the Purple Pig, maybe a little bit longer walk up north, although that may be difficult to get into on a Friday night (but everything is going to be pretty crowded, I would think.) For old-school Chicago, there’s Miller’s Pub on Wabash. The food is not anything particularly exceptional, but it’s got that 50s/60s Chicago vibe to it (the bar itself dates back to the 30s, but was bought up in the 50s and turned into a bar and restaurant.)

Also, the Billy Goat Tavern might be a fun visit for a neighborhood tavern feel in the middle of downtown Chicago. It gets its share of tourists, of course, being made famous from the “Cheezborger, cheezborger, cheezborger” SNL sketch, but is still populated by businessmen and journos from the Chicago Tribune (used to be even moreso a newspaper hangout when the Sun-Times building was still there, now replaced by the Trump Tower.) This is the Hubbard Street location, on the corner of Hubbard and Lower Michigan Avenue, so you have to go down a level from surface level Michigan Avenue to get to it. There’s nothing fancy about it, but it really does feel like an old-school Chicago tavern to me, minus the occasional bus of tourists. If you get a cheeseburger, get at least a double, as the patties are very thin (fast-food like) and the Kaiser buns are fairly substantial. This is the kind of place I go to and order an Old Style and Old Overholt and get a double cheeseburger, which you then dress yourself with thickly sliced onions and pickles. Here’s a video of it so you can gauge whether it’s something that may interest you.

Wow, thanks for all the great ideas!

So it turned out that one of my sister’s colleagues we just as excited about Wrigley as I was, so we went down there today. Turns out no tours because of the Kerry Woods Battle of the Bats Charity Home Run Derby was going on, we got to go in and watch that. Then, one of the guest ambassadors came over and asked if we were the ladies who had wanted a tour. We said yes, and she said she couldn’t give us one, but talked to us for a long time about the history of the park, architecture, the team all kinds of stuff. It was really pretty cool.

We also rode the El and visited the Art Institute today.

Turns out the award dinner my sister and her colleagues are going to Friday evening is at The Berghoff, so I will probably eat there separately that night, since it’s highly recommended. Then I can walk around the park until they are done with the boring part of the meal. :wink:

We are seriously considering the architecture boat tour for tomorrow. I am passing on all these recomendations for restarants to the group because we are together for dinner Sat, Sun and Mon and this is a first visit to Chicago for all of us.

Yep, I was going to say, don’t bother with Navy Pier (unless a festival or something) except for this. So much fun. I did it in absolutely frigid weather last time, and it was still a treat. I grew up near Chicago, my grandfather was an architect who worked on a lot of the iconic buildings on the tour, and it was so much fun hearing the tour guide on the little cruise (himself an architectural student) wax on about all the buildings. I knew in an academic sense how the Chicago shoreline had changed and adapted in the Victorian era due to commerce and growth, but they really explained how the buildup, the locks, the divertings of the river, etc. worked.

Since you are in the area, you can’t do wrong with a few of the museums. The Science and Industry is huge and a lot of fun (with many hands-on exhibits, and bits of local goodies–do the Coal Mine for sure!) and the Field is the best out of ANY natural history museum I’ve visited (My recommendation is to chill out in the Gem Exhibit and the upstairs Botanical, but that’s just me). Plus there’s like 4 decent art museums within walking or two bus stop distance. Also, the annual Chicago Summerdance Fest in Grant Park is probably going on, and that’s awesome, free, and lots of things to participate in.

As for weather, t-shirts and shorts or sundresses. It’ll be hot and muggy, most likely. Just bring a shrug or cardigan if you get chilled at night. The “Windy City” bit is most obvious in winter.

Not sure of the timing, but there’s free classical music tonight at Grant Park. You can walk there from the Berghoff.

Stay away from the inner city and the black areas.