24 hours in Chicago in Mid-July...what MUST I do?

You got museums(AC is good on a blistering hot humid day) , must try foods, and sightseeing ( on a boat? just watch out for the Dave Matthew’s tour bus! Lol)

But don’t rule out renting city bikes and pedaling along the lakeshore soaking up ambience and sunshine. Boats, joggers, bikers, amazing skyline it’s all good.

Prepare for Traffic. Fact of life. Excruciating if it’s festival or a sporting event.

If you do want to park downtown, use a parking app like ParkWhiz or SpotHero – it will save you a lot of money and frustration finding the most affordable places to park. I drive downtown all the time and would never park anywhere without first booking a spot using the app. You can find spots for $10-$15 for most of the day often with it, where you’d normally pay $25-$50+. (For example, right now I can find a few spots within a block of the Art Instititute for $12-$13 for 12 hours of parking.)

That said, the Orange Line is convenient – I live one stop from Midway – about 20 minutes-ish to get to downtown and that train line circles the Loop, so another 8-12 minutes or so to get to the northeast end of the Loop tracks (where you’ll want to get off if you want to hit Millennium Park.) For touristly stuff, I might get off at State & Lake, take some pics in front of the Chicago Theatre, walk up north to the river, go down the riverwalk and walk east to Michigan Avenue, take in the nice view of the Wrigley Building, the former Tribune tower, and even the Trump tower is quite nice (minus the giant Trump letters) – walk up to Michigan Ave., then walk south on the east side of the street to get to Millennium Park. If you walk north instead, you get to the “Magnifiscent Mile” stretch of Michigan Avenue, which is mostly a shopping district. I don’t find it personally that interesting except for the bustle, but if you walk far enough north, you’ll get to the Water Tower. Unless you want to do a good bit of extra walking, I’d just go south, hit Millennium Park, and I personally love the Art Institute. Further south yet is the museum campus, which has the Shedd Aquarium, the Field Museum, and the Adler Planetarium. The strip of land between the Shedd and Adler provides a nice panorama of Chicago, and one of the “postcard shots” you see of the city. That whole walk would be about 2 1/2 - 3 miles (without detouring north on Michigan.)

There are other cool spots within the Loop to see – the Chicago Board of Trade, maybe the Picasso at Daley Center depending on what you feel about it – there’s a nice lChagall mosaic titled “Four Seasons” at the Chase Tower Plaza that I personally quite like (20 S. Dearborn). Oh, the Chicago Cultural Center is free, and that’s on Michigan and Randolph.

If not for the kid’s request, I’d skip the Adler. Cool view of the skyline, though.

And I’d stick with a deep dish Chicago pie so you can properly refute Jon Stewart’s incorrect sneering rant. I haven’t had it myself in at least a few years but it’s really good and will have that spectacular cheese-pull photoshoot moment. Italian sausage is, in my opinion, a must.

I know some poopoo it but you could do far worse than Portillo’s. Perfectly acceptable dogs and beefs, and maybe consider a Maxwell Polish sausage and a chopped salad, both are very well executed there.

If OP’s route has them on I-90 (the Kennedy) on the North side, I recommend a stop at American Science & Surplus. It’s easy-on-easy-off the interstate and a really fun place to visit. The astronomy fans in the fam will appreciate that they sell telescopes.


Yes. If you eat meat, sausage is the king of pizza toppings here. It’s not a pepperoni town. You’ll find pepperoni, but it’s not the default meat topping.

Just a thought, if you can swing the price getting a hotel downtown will make the sight-seeing portion of the trip a lot more profitable. The neighborhood around Midway is pretty awful and you’re going to be highly isolated from anything of touristic merits. The Chicago Hilton or Palmer House each could be an interesting historic option for not a crap ton of money. I understand the whole getting to the airport fast thing on the day of your flight, but Midway isn’t hard to get to from the loop.

For my money, stuffed is a lot better than deep dish.

I’m the opposite: definitely prefer deep dish; I like some stuffed, but not Giordano’s. Thin crust tavern pizza is my bag, though.

Driving in Chicago is a nightmare. It will not save you any money or time. If you’re driving in from Iowa here’s how I’d manage the logistics. Drive in as early as humanly possible and head straight for a hotel downtown and pay the painful price to park the car overnight. Forget about it until you head to the airport. Use Lyft or Uber generously. There will be a ton of drivers out and it save you a lot of time. The L system is excellent if you know what you’re doing and the departure and destination are close to stops, but with the short amount of time you have even a short wait at the station and a short walk to and from could eat up an hour or more of your stay. When you head out to the airport stick it in the Midway Daily Lot. There are of course cheaper ways to go, but you’ll be sacrificing a lot of precious time with each compromise.

If you instead use the Midway hotel as your home base you’ll save on parking and you’ll have an easy time the morning of the flight, but once you head downtown for the sightseeing you’re going to be committed for the full day which can add some stress.

Great Tavern Style > Pequods > Stuffed > Mediocre Tavern Style > Deep Dish


I’m up with you until there. :slight_smile: I’ll put Burt’s over Pequod’s for that style (which some/most characterize as a type of deep dish – but I characterize it as an offshoot), but a) I haven’t been to Burt’s since he passed away and b) it’s technically not in Chicago (Morton Grove.) but c) it’s the same lineage, as Burt Katz opened the original Pequod’s in Morton Grove, so of course they’re very similar. That said, if I were to send someone on a Chicago pizza experience, I’d send them to Pequod’s, most likely, even if it’s not exactly the traditional style of deep dish.

This really won’t work for you with an 11 year-old but I have to mention Joe’s On Broadway, 3563 N. Broadway, 312-528-1054. Just a local tavern.

P.S. I am not from Chicago but if I pass through and have the time I visit Joe’s for their free Thursday afternoon hot dogs.

Yeah. I had assumed they were flying in/out of Midway. No idea why someone would choose to stay there if there wasn’t a clear reason. Not clear how much $ is an object, but plenty of places downtown-ish, or convenient to CTA/Metra.

IIRC, driving down Cicero to Midway there have long been a couple of dumpy hotels in various stages of decay! Everytime I pass them, I joke something along the lines of, “That looks like a nice place to stay!” :smiley:

Yeah, our local civic association has been doing their damnedest about getting Cicero cleaned up for quite some time now. Most of the dumpy stuff is north of 47th. Once you hit Archer, heading south, it’s cleaned up a bit, with the Midway Beautification Program (or maybe it’s South Cicero Corridor Beautification Program – whatever the exact name is) and all that.

The hotels in the Midway Hotel center are perfectly normal business hotels, and even some of the ones not in that area (like the Carlton near Archer & Pulaski) are fine, as well.

I’m a mile and a half NE of the airport. The area is an odd one to choose if touristy things is your goal but, it is cheaper to stay around here, it is proximate to the El (and one of the nicer lines, given its the most recent if you don’t count the Pink, which doesn’t use new tracks), and it’s a relatively quick hop to get downtown. It’s also only a short distance from I-55/the Stevenson. Hell, if you want to take a slower route, drive down Archer, though there’s not a heck of a whole lot to see except city life and Chinatown towards the end.

If you want some of the best goat birria in the US, you’re not far from Zaragosa’s on 49th and Pulaski. :slight_smile: But that’s ultra food nerdy stuff. I can give you a bunch of those. Also, for the best tavern style pizza, Vito and Nick’s at 84th and Pulaski. But you should rather spend your time in the downtown area.

What’s up with those 2 big undeveloped tracts - on the E side of Cicero just S of 31st, and on the W side S of the Stevenson? Those just always strike me as odd.

I think the one really dumpy hotel was S of 45th. I’m usually coming down from the Ike. Rarely make it S of the airport cell lot.

Don’t know much about the area around 31st Street. The other one used to be LeClaire Courts public housing, but was razed in 2011. There is a development that’s supposed to go up there.

Right now, though, it’s still just fenced off empty land with a bunch of trees.

The dumpy hotel you’re talking about is now Cicero Hotel, formerly, Sportsman’s Inn. It looked a lot worse as the Sportsman’s Inn. That place was an absolute dump. I don’t think anybody in the neighborhood wants that motel there, but we pressured them to at least renovate the property. The Cicero Hotel doesn’t look quite as bad, and the pictures I see of its interior rooms on Google make it look much, much nicer than it was.

Ah yes - the Sportsman’s! :smiley: I remember that name. The Streetview pics look much nicer than I remembered.

Good job on your community’s efforts. That area is a completely different city than my old stomping grounds on the NW side.

I am totally into astronomy (and was when I was a kid), but I would still put the Adler Planetarium fourth on the list, behind (1) The Museum of Science and Industry, (2) the Field Museum, and (3) the Shedd Aquarium. MoS&I was just about my favorite place in the world when I was that age. On the other hand, as mentioned, Adler, Shedd and Field Museum are in walking distance of each other, so some combination of those might make sense for a single day’s outing.

I’ve always wanted to try that place, based on things I have read. Do you know if they’re still doing the cash only thing?

Not a deal breaker, but I’d have to plan ahead, such as stop at the ATM. Thanks.

I was curious, so I just looked at their web site. There’s a little banner which does, in fact, say, “Cash only!”


Ok, so what is the deep dish vs tavern style vs pequods(! ?) thing?

Do I need to get three types of pizza in 24 hours? Because, I will if I have to. For science! But if I don’t I might go somewhere else.

Also, the hotel is not my planning department. My wife wants to stay close to the airport so her stress levels on the day we leave are low. I can maybe make a suggestion or two, but that’s probably not moving.

Deep dish is what most non-Chicagoans picture when they hear “Chicago-style pizza.” It has a thick crust, as well as a very thick layer of toppings. Pizzeria Uno was the originator of the style, and Lou Malnati’s (started by a guy who originally worked at Uno, and whose father was instrumental in orginating the style) is another big local chain for deep dish. This is a Pizzeria Uno pizza:

“Stuffed” is a variation on deep-dish, and is what Giordano’s (another local chain) offers:

Pequod’s is a local place with their own variation on deep dish (I’ve not eaten there, but it’s well-regarded). Their pizza:

“Tavern style” is the kind of pizza that is actually more commonly eaten in Chicago, and more commonly made by the local pizza places. Very thin (and usually crisp) crust (the term “cracker crust” is often used), and usually cut into squares, like so: