30 relaxing hours in Chicago
August 9, 2022 9:01 AM   Subscribe

In October, we are flying into Midway, arriving about 3pm on a Sunday, and flying out of O'Hare at 10pm the next day. We will be finishing up a potentially hectic and stressful three weeks in the states before our long flight back to the UK so would like to have a fun and relaxing time to wind down.

So basically we will fly in to Midway, go drop our stuff at a hotel, lounge around until dinner, sleep in the next day, ask the hotel to hold our luggage, do...something... until it's time to head to the airport, and then we will go back to the hotel to pick up our luggage and get a taxi to the airport. I think we'll need to be at the airport by 7pm.

Specific questions:

Where should we stay? Next to O'Hare, or somewhere adjacent to the "something" we would find to do on Monday afternoon? Do you have any specific neighbourhoods or hotels to suggest and any places to eat for Sunday night? I've always had great Mexican food in Chicago (though this would have been 20+ years ago now) and would love any suggestions for casual but amazing Mexican food.

What is the "something" we should do on Monday afternoon? Where should we eat lunch? I am not desperate for any kind of amazing cultural experience- we're actually spending three nights in Chicago at the beginning of our trip and will be doing plenty of cultural stuff then.

What actually might be nice is a generic American shopping experience, just as an example ,if there is somewhere with a Target and a Barnes and Noble in close proximity where I could pick up some last minute stuff I can't get in the UK, pick up some magazines at the B&N, and then have Shake Shack or some other decent junk food for dinner before heading to the airport-that would probably be exactly the level I'm looking for. But if you've got something a bit less mega-chain shopping oriented, I'm happy to hear those ideas as well!
posted by cilantro to Travel & Transportation around Chicago, IL (6 answers total)
Best answer: Don't bother staying out by O'Hare--there's nothing at all to do near the airport, so you'd spend all day on the CTA getting back and forth. I would suggest staying in the Loop near the Blue Line, which takes you directly to the airport. The Loop will have your Target/B&N (it's the DePaul University bookstore)/Shake Shack access, and plenty of places to eat. It isn't the most adventurous option but that's not what you're looking for!

For dinner Sunday I would suggest just heading to the Fulton Market area and seeing what hits your eye. But if you're up for a small journey, take the blue line to Logan Square and try El Cid for casual great Mexican.
posted by We put our faith in Blast Hardcheese at 9:26 AM on August 9, 2022 [5 favorites]

Best answer: If the weather is good, hanging out in the gardens in the Loop is nice during the day. Take one of the sunset architecture boat tours Sunday evening.
posted by Candleman at 10:32 AM on August 9, 2022 [1 favorite]

Best answer: I'd stay near your "something" for sure, rather than staying by either airport. Getting from Midway to O'Hare (or vice versa) is an unqualified nightmare most of the time. On several occasions it has taken me longer than my cross-country flight.

If you've done a lot of the Big Sights, pick a neighborhood! I live there so I have to plug both Andersonville (Clark Street) and Lincoln Square (Lincoln Ave) -- they're close enough to each other that you could hit both if you wanted. The main streets are perfect for strolling, shopping, eating, and drinking; sidewalk cafes will still probably be open in October if that's your jam. Andersonville in particular is likely to have a very pleasant and lively street scene even on a Monday. Both neighborhoods have great bookstores (Women & Children First and Book Cellar, respectively, plus a couple of used bookstores), and the Broadway and Peterson Targets are not too far away either if you still want to stop by there. XOchimilco in Lincoln Square is my favorite casual-but-amazing Mexican spot at the moment. It's outrageously good, and BYOB. Pretty much the food here is all good though, that's what Chicago is about.

Re: logistics, you can hop the Lawrence or Foster bus to the blue line for the airport, it takes roughly an hour total (or of course you can get a cab -- during rush hour I'll often catch a cab just to the blue line, because I-90 is a hot mess and the train is absolutely faster -- calculus is a little different and more cab-favorable if you're flying out of Terminal 5). There's not a huge density of hotels in the neighborhood -- The Guesthouse is in Andersonville but expensive iirc, otherwise you're looking at staying down near Wrigley Field, but that can be fun in its own right, plus it's an easy hop on the train or bus to get to the other neighborhoods.

(for generic american shopping experience ft. barnes & noble, yep, gotta be the south loop. most of the barnes and nobles are gone!)
posted by goodbyewaffles at 11:09 AM on August 9, 2022 [1 favorite]

Best answer: Rosemont has a bunch of decent hotels to stay in on River road, features a 'fashion outlet mall' which is decidedly a whole scene, with loads of very American suburban dining choices. It puts you a short car ride (~10 mins) from either a giant Target shopping store, or a 'fancy' giant super market Marianos. You could also get a proper hot dog from the locally beloved Paradise Pup, which is also just up the road. Most of these Rosemont hotels will offer a shuttle to the OHare.

As for for a magazine or two - the O'hare has a bunch of options including a Barbara's bookstore. If you haven't been to the airport you should probably double the amount of time you anticipate spending navigating through it. We are spending just short of 10 billion renovating, so who knows what it will be like in October, but I predict worse.
posted by zenon at 11:35 AM on August 9, 2022 [2 favorites]

Best answer: You can take the orange to the blue line on Sunday and come to Logan Square! The blue line leaves from Logan and it is the best way to get to O'Hare, especially in the afternoon on a weekday.

Across the street from the train is Longman & Eagle, a cute boutique hotel and delicious restaurant. El Cid (mentioned above) is three doors down and has great margaritas if you would like Mexican. There is a Target a pleasant 8 minute walk away, and you can hit City Lit (a small bookstore). There's a bunch of small shops near the square and up/down Milwaukee, plus some lovely restaurants and bars.

Logan Square boosterism aside, though, staying in the Loop will let you hit those specific stores / junk food needs. (And you can go to Primark if you really miss the UK!) Taking an architecture boat tour is lovely even if you don't care about architecture; who doesn't love a beer on a boat? Staying in the Loop means you'd be very close to museums; even a quick wander through the Thorne Rooms is a delight.
posted by quadrilaterals at 1:23 PM on August 9, 2022 [3 favorites]

Best answer: Logan Square is a great place to eat and for access to ORD. You could spend an afternoon walking around, window-shopping and eating if that's all you want to do. There's lots of boutique-type places along Milwaukee Avenue (a diagonal street) between Diversey and California. There's even a shop called Wolfbait and B Girls that only (mostly?) sells stuff made in Chicago. There's a smaller "city" Target (8 minutes walk mentioned above) nearby everything, but also a very large and busy Target with way, way more junk to buy on the far Eastern side of Logan Square on Elston Avenue. If I wanted to peruse junk I could buy cheap in the US I would go to the big one on Elston (more clothes, housewares, beauty, grocery, etc.)

If you're eating Mexican in Logan Square El Cid is nice and standard Mexican (walk through to the patio behind the restaurant for the best ambiance). If you want some hipster Mexican food, check out Lonesome Rose and eat on the rooftop deck. Or go even more authentic and hit up Jibaritos y Mas for a Puerto Rican Jibarito (sandwich with plantains as the "bread." It's a ways from the other stuff, but you'd see a lot of the residential parts of the neighborhood. They have a takeout and dine in as separate entrances and it's not fancy, probably more of a lunch place than a relax and enjoy the ambiance place.

If you want some good old fashioned American junk food (what I call "normal food") you could get a Chicago hotdog and cheese fries (or how about an Italian beef) at Victory Grill near the California blue line station. Or, get more or less the same stuff at Mr. E's, closer to the Logan blue line station. Want your greasy food more like on a fried chicken sandwich in an outdoor patio? Head over to Parson's. While there's lots of fancy places to eat, you could get breakfast or lunch at a regular American diner—Cozy Corner under the California blue line station has you covered.

If you want an American shopping experience with chain stores, Logan Square isn't really the best place. First of all, you will have the best selection of magazines at a bookstore at the airport (although City Lit is a great bookshop, so check it out anyway). I wouldn't seek out a B&N just for magazines. There's two areas I would send you to for generic national brand stores—either along Michigan Avenue and State street (so, stay overnight in the loop) or around the intersection of North & Clybourn on the west side of Lincoln Park (I don't know of any hotels nearby and it's very car-centric despite the red line stop and buses nearby). I'd probably pick the loop/downtown option if I were choosing between the two.
posted by Bunglegirl at 5:29 PM on August 9, 2022 [1 favorite]

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