corporate-wage-slave

Yes ORD was a bit of a revelation to me. I had usually used ORD to transfer and wasn't that familiar with downtown, my few visits often enforced thanks to bad weather and not conducive to strolling around. I then had a couple of days there and discovered that the buildings of Chicago are quite amazing. It seems there are many ways to construct a skyscraper, and Chicago has a leading example of each method. The thing to do is to download a walking tour or two on to your phone - there are dozens online and mostly free of charge - and work your way around the city. Here is one I used recently. It starts at the Chicago Cultural Center (which started life as the Central Library and the meeting hall for the Grand Army of the Republic in a bizarre timeshare arrangement) and ends at the Willis Tower, probably still better known as the Sears Tower.

BlueThroughCrimp

Been a while since I've been to Chicago, but if you do one tower, I thought the Hancock was better, and the outside area at night, listening to the city soundscape was quite impressive.

Spinstorm

I checked all the US destinations and the only timing that works to give me the whole of Saturday is Chicago. I am double checking but I think that is where I will end up going.

I would have probably chosen Nashville as my favourite choice but no flights that arrive until the end of Saturday.

How is AA compared to BA? Can I upgrade an Economy redemption in the airport? (Not that it looks like there is any business available anyway).

Spinstorm

I booked onto Chicago (used all my avios and £372 in taxes) - thanks to Gold I got my front of economy seat so I should have good space on the 787.

I reserved the W City Centre for £391 - and I have submitted a price match request to Marriot to see if they will match and give me the 25% off.
@corporate-wage-slave thanks for the walking map

MSPeconomist

tynmar

Spinstorm

I am still wondering is there anyway to upgrade my avios redemption at the airport if there is availability?

windowontheAside

As I understand it American will sell AUPs on redemptions, but of course you'd get no extra TPs and Avios. (BA wouldn't give them either on a redemption, but AA don't even on cash tickets).

sondra_finchley

With Chicago - be aware that CBD area can be completely dead and devoid of open restaurant options on weekend evenings, sort of like how City of London has some great restaurants but you need to check if they are open on weekends (and usually aren't). Its also a city of neighborhoods, so you want to get out into them - go north into Lincoln Park and Wicker Park (or even up to Evanston) to wander around and lots of good bars/restaurants/cafes etc. Museum of Industry is always worth seeing, and there are a ton of other museums, parks, live theatre and comedy clubs, jazz and blues, etc.

You really can't beat it for walkability however the weather, especially at this time of year, can be unpredictable and occasionally quite violent if you aren't used to spring Midwestern storms. Its been a rather cool/cold spring so here's hoping your trip will be much warmer! Oh and try and get to a baseball game too (Cubs up in Wrigleyville, or the Sox down in well, down in the South area somewhere. I'm a Brewers fan, we only care about the Cubs) Wrigley Field really is somewhere to take in a game - you can walk up to the ticket office and see what they have, buy a ticket online in advance (probably adviseable as this is a dream stop sort of stadium for any baesball fan), or see what the scalpers have on the street (discretely). Looks like Cubs are at home against the Cincinnati Reds that weekend with two day games (1.20 pm start, not a 7.05 pm start). Even if you don't go to the stadium you could probably pass a few fun/interesting hours in a bar nearby!

You'll have a great time, and the Blue line makes the Picadilly to LHR look like a luxury train service.

Quick edit - If anyone is considering another US option in the future - can absolutely recommend CHARLESTON. Did we have a great time there - fantastic city and wish we had spent more time. And just the most adorable, stress-free, comfortable little airport. Added bonus - Boeing builds the 787 on a line there so we watched an Air France go out for an hour test flight, and not one, not two, but THREE of the four Dreamlifters arrive and taxi past the main terminal.

Spinstorm