30 relaxing hours in Chicago

Post date: 2022-08-10 05:01:32

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!

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