How to spend a free day in Chicago

May 1, 2023 8:20 AM

I've got a free day next monday to spend in Chicago, and i'd like to enjoy it, so hope me...

I'm interested in museums and some architecture. I'm going to an event in Waukegan over the weekend, but not flying out until 7ish monday night. I don't yet have a room booked for sunday night, becasue i'm not sure how to approach my day in the city. Do I stay near the airport and use public to get downtown? do i stay downtown, near the sites i want to see to avoid moving the car and finding day parking? Is there a cluster of must-see things to make it easy? I'm not likely to want to do a "tour", and i'm more interested in an art museum than and natural history or science museum.
Thanks

posted by OHenryPacey to Travel & Transportation around Chicago, IL (18 answers total)

I can't speak very well to the logistics, but I will say you could spend a delightful day at either the Art Institute or the Field Museum.
posted by humbug at 8:22 AM on May 1, 2023 [5 favorites]

No idea about travel logistics, but based on your description of your interests, i would say focus on the Art Institute of Chicago, and make time for the short walk to the Chicago Cultural Center and stare in awe at the Tiffany glass domes. I've spent many a weekend in Chicago, and this is by far one of my favorite things to go see
posted by darsh at 8:28 AM on May 1, 2023 [1 favorite]

Best answer: Yes, stay downtown and take the train to get there. You may find that you can get a better than expected deal on a hotel room if you focus on the business-oriented hotels that primarily cater to people in town for a meeting/event during the week. If the weather is nice (and it's Chicago, so really who knows) Millennium Park is terrific for some outdoor time.

Chicago has so many of the best restaurants for every style and price point. If you give us some parameters (vegan, vegetarian, or meateater; price range, atmosphere; favorite cuisines) we can probably recommend some life-changing stuff.
posted by DirtyOldTown at 8:35 AM on May 1, 2023 [1 favorite]

Grant park of course! Then cindy's for a view from above, a great drink, lunch. A cubs game would be pretty cool as well - then poke around that historic neighborhood, a Jazz club in the evening is a must if can pack it in.
posted by specialk420 at 8:38 AM on May 1, 2023

The Museum of Science and Industry could also fill up a while day.
posted by mmascolino at 8:43 AM on May 1, 2023 [2 favorites]

I agree that the Art Institute is amazing! I know you said you’re not a tour person, but it could also be worth considering an architecture boat tour—I did this some 15 years ago and still remember how cool it was. There are various companies that offer these, and I vaguely recall concluding that the Chicago Architecture Center was the best option, but it would be worth some research to confirm that if you decide to do this. Have fun!
posted by bijoubijou at 10:45 AM on May 1, 2023 [1 favorite]

Which airport are you flying out from Monday at 7:00pm? Depending on which one, you will absolutely need to be at the airport at 5:00pm, and then you'll have rush hour traffic to contend with, both of which will limit your "full day." So I'd advise to stay at the airport Sunday night and use public transpo to get in and out of the city. I really really really don't suggest that you try to drive to the airport from downtown. I've done that in non rush hour conditions and it was still hell.
posted by cooker girl at 11:07 AM on May 1, 2023 [2 favorites]

Best answer: In terms of art:

• Art Institute of Chicago: currently running a Salvador Dalí thing, but the modern wing is generally the primary destination for me. Can easily consume an entire day - and the cafe is fine for a mid visit break.
• MCA. The C stands for Contemporary, so if you are up for grappling with modern art then this is your top destination. It's about a 10$ taxi north of the Art Institute.
• Hyde Park is south of the city core, and covers both art and architecture with the Robi house and a number of museums including the Smart museum. There is also the often overlooked, you know, because racism, oldest independent African American collection housed at the DuSable Museum, but that is closed Mondays.
• Another destination suggestion for capital A art would usually include National Museum of Mexican Art but it is still under renovations. Otherwise it should be considered a true gem when all galleries are operational.
• Niche art museums: Museum of Contemporary Photography and American Writers Museum are in the downtown core and both are great smaller operations. Unlike the Chicago Sports museum collection, which is just someone's tax write off and truly without merit.
• on the extra touristy side of 'experience' based productions there's an immersive Mozart thing, that I'm only including in the off chance that that you love Mozart or looking for fodder for your instagram. Otherwise the claim to use "state-of-the-art Artificial Intelligence as inspiration" is enough for me to know it's not my sort of experience.

As for getting around - staying downtown makes your drive out to the airport more time sensitive - Google maps lets you choose travel dates to help predict the travel times you should plan for. You will pay for that downtown location, but it's worth it for me and I live here. Expect parking to cost at least 20 for 4 hours and a biz day can start between 30 and 40, even if you are out by 2. Hyde Park becomes more attractive destination if you are using Midway airport, where driving all over isn't as onerous, and you'll be able to sort out parking there without great cost or hassle. Staying at Ohare and taking public transit in and out adds complexity but is faster, more reliable and much cheaper to get around the downtown core. I'm a big fan of the El, but I would weigh how much navigating the transit system adds extra stress to your visit vs the extra costs in money and time of driving around.
posted by zenon at 1:04 PM on May 1, 2023 [1 favorite]

The Blue Line runs from O'Hare to downtown in about 45 minutes. It will feel like a long time, but it's faster than driving and parking.

The Art Institute and Grant Park are right downtown. The Museum of Contemporary Art is about 1.5 miles north— a walk you might want to take anyway, as part of it is the Magnificent Mile.
posted by zompist at 2:14 PM on May 1, 2023 [1 favorite]

Driehaus Museum is fun if you're a fan of the late 19th century aesthetic. It was a Gilded Age mansion which Richard Driehaus bought to house his collection of objects and furniture from that era and then turned into a museum. They give guided tours and currently have an exhibition about Louis Sullivan.
posted by Constance Mirabella at 3:51 PM on May 1, 2023 [1 favorite]

I recommend staying downtown Sunday night. On Monday go to the Art Institute. You could spend the whole day there, but if you want to break up the day, you could either walk around and check out outdoor art in the area (Picasso sculpture in Daley Center, The bean, Chagall mosaic, etc.) Or the Chicago architecture tour on the river is so great. Then drive to the airport, leave around 4ish to drop off rental, etc, if you're flying out if OHare. Have fun!
posted by j810c at 7:16 PM on May 1, 2023 [1 favorite]

Nthing the idea of train from the airport to downtown. In general, a car in a city you don't know well like Chicago tends to just be a pain. Older cities like Chicago usually have better public transportation, and more taxi service, plus walkable areas, than newer ones.

Getting a room at one of the 'business' oriented hotels is, I believe, a good idea. I haven't been in a number of years, but Swissotel was good location. There's a mall underground near there which has places to eat. Also, if you are not vegan, I always recommend Billy Goat's Tavern, lower level Michigan (actually go downstairs across from the Wrigley Building, turn right, and it's there) - the inspiration for the "cheeseborger" SNL skit but in any event a bar and grille in the traditional sense and remember "chips, no fries" - they basically have a Waffle House-type griddle they cook on.

The Art Institute is fantastic and worth a short walk from the hotel. The Palmer House hotel is _very_ close to the Art Institute but I don't know what it is like now because I last stayed there about 15 years ago.

I found Chicago very walkable myself but I am pretty good at being aware of my surroundings, walking confidently as though I know what I am doing, etcetera. If it makes you nervous, take a cab from the hotel for your destinations.

I wish I could remember the names of places I ate that are likely to still be there, but I'm drawing a blank right now except for Billy Goat's.
posted by TimHare at 9:45 PM on May 1, 2023 [1 favorite]

Best answer: If you can make it to Chicago late Sunday afternoon, I would recommend one of the sunset architecture tours. The Chicago Architecture Foundation are the most praised ones here but I had a great experience with the Shoreline Sightseeing one (and they leave a little later). Or perhaps take one of the daytime ones first thing in the morning.

I know you say you're less interested in tours and I generally am not as well, but there's no other practical way for a tourist to see the architecture from the water (unless you want to rent a boat) and having a knowledgeable guide pointing out the things I wouldn't know to look for was useful.

For Monday, given that you like art, the Art Institute is a no-brainer. It's big enough you can easily spend an entire day there and is adjacent to the Millennium Park such that you can pop out for fresh air and greenery if you need a break. There's other museums in the area but with only a single day, I'd just expect to spend all of your time there. Definitely heed the warnings about rush hour commutes as far as scheduling.

Do I stay near the airport and use public to get downtown? do i stay downtown, near the sites i want to see to avoid moving the car and finding day parking?

How cost sensitive are you? The downtown hotels are going to be more expensive and will charge you for parking and rush hour traffic will make getting to the airport more stressful. But they'd save you time if you're trying to do things Sunday night and let you get out and do more things.

It gets more fiddly, but you could return the car Sunday, catch public transit downtown, stay there overnight, and take transit back out for your flight. If you don't have a lot of baggage, this might be for the win, as it would give you an easy straight shot on the way out. Do you want to optimize for free time Sunday or Monday?
posted by Candleman at 6:08 AM on May 2, 2023

Response by poster: Thanks so much for all of the great answers. This was exactly what I was hoping AskMe would provide.
I have filed away the suggestions that will serve me well on future visits, and marked as best those that helped me decide for this trip. I am planning to drop my car at the airport sunday evening and take the blue line into town where i'll stay close to the Art Institute, my main destination, to be followed by some of the other suggestions nearby. Then a timely train ride back to O'Hare.
I guess my one follow-up would be for one of those life-changing meals , likely for sunday night...?
posted by OHenryPacey at 7:00 AM on May 2, 2023 [2 favorites]

I guess my one follow-up would be for one of those life-changing meals , likely for sunday night...?

It might be a bit hard to get a reservation for the truly otherworldly (Alinea, etc.) at this short of notice, but for a Sunday night if you're not fussy about time...maybe not impossible? Some other places to consider: The Aviary, Monteverde, Girl and the Goat, Avec, Bar Mar.

The aforementioned Cindy's has fine-to-great food, not magic, but the experience is thoroughly a delight. The Cherry Circle Room (also in the Athletic Association Hotel) is similar--a meal and a drink right out of Mad Men, sumptuous interior, secret sexy lair vibes, excellent steak, bespoke martinis.

Also, I'll say it: people say Au Cheval's burger is overrated and they are incorrect. Those are good burgers, Walter. (YMMV for the assorted Small Cheval locations, which are some good and some meh.)
posted by We put our faith in Blast Hardcheese at 7:53 PM on May 2, 2023 [4 favorites]

A note from the other Chicago thread:

A transit note: the Blue Line has closures Friday--Sunday between Addison and Western; so no service to California, Logan, or Belmont stations by the train. They have shuttle buses running express for those stops.

Something to be aware of though it doesn't look like it'll impact you (but check to make sure there's not more closures).

I guess my one follow-up would be for one of those life-changing meals , likely for sunday night...?

Your challenge here is that the lofty restaurants frequently require a 2 person reservation and few have lunch hours so you'd be limited to Sunday night. Alinea is one of the standard bearers of modernist cuisine if you can get a spot there. None of the other Michelin starred restaurants look bad either. I have been told that Moody Tongue is worth it by trustworthy foodie friends but not been myself.
posted by Candleman at 7:55 PM on May 2, 2023 [1 favorite]

Also on the food note, Three Dots and a Dash recently won some big name award or other. It's an absolutely fine bar and restaurant but not life changing in any way, so while it's a great choice if you happen to be in the area, I would not travel out of my way for it.
posted by Candleman at 8:00 PM on May 2, 2023

Not knowing too much about your dietary preferences, I'd say a real treat might be to look into the restaurants in the West loop, which is where a lot of the newer upscale (but not like Alinea expensive) restaurants are located: the aforementioned Girl and Goat (as well as its sister restaurants, Little Goat Diner and Duck Duck Goat) and Au Cheval; as well as Rose Mary, Alla Vita, The Loyalist, Avec, The Publican... there are so many.
posted by DirtyOldTown at 8:14 AM on May 3, 2023 [3 favorites]