stop over in chicago - a quick exploration ?
 

we are arriving in Chicago at 3pm (= 5pm I gather by the time we clear immigration) flying out the next morning to Phoenix. Staying at the Hilton in O'hare. Current plan - train into downtown, get off at the loop, look at lake Michigan, quick boat trip if we have time, a walk along a bit of the magnificent mile, cab to somewhere like gibson's for food, then back to O'Hare before midnight.

Is that possible?

If you take the L you'll get downtown around 6pm. I'm just max out times for customs, checking in to the Hilton, and the L is a 45 min ride ORD - downtown. Then you'll have to get to wherever you want to take a boat ride. You'll ride during dusk, grab late dinner. Have fun!

Also - as a Chicago native, the blue line to/from ORD is terrible. But enjoy. Haha.

It is fine though not a lot of time. If its a weekend, there will be less people during rush hour but if you dont mind going into the city for a couple of hours, sure why not and have fun!

thanks guys - thought it might be a bit overambitious - how about a trip into town - a stroll along the lakeside and then back to O'Hare for a bite to eat at the hotel - anyone know the best place to get off the L for that purpose?

don't suppose it would work out quicker using a cab?

Would probably be a little quicker with a cab, but not by much and maybe slower at rush hour.

Cab would be maybe 8-12 times the cost of 2 L tickets.

If you time it right and don't mind getting back late, you could go to the theater. Or just walk around Millennium Park, Mag Mile, etc.

I think you have a lot on your to-do list, but it can be accomplished.

Presumably you want to stroll along the lake somewhere between Oak Street (to the north) and Roosevelt (to the south). Depending on your budget, you might consider drinks or dinner at Spiaggia/Cafe Spiaggia or J. Parker. (J. Parker is actually about 5 minutes north of Oak Street via cab.) Spiaggia is located adjacent to an underpass that will take you to the beach/lakefront and is also at the north end of the Magnificent Mile. (It's not far from Gibson's either.) I'd probably ditch the idea of a boat ride. I *think* most of the evening lake cruises are dinner cruises, so you're probably looking at a couple hours for that.

None of the Blue Line L stops are particularly convenient to the Magnificent Mile. The best you'll do is into the Loop and then walk/cab/bus north or east to the lakefront. Depending on when you're ready to head to the city, you might just want to do a cab. (You can easily check Chicago traffic conditions on Google.)

Why not get off on Washington, walk straight east. Check out Millineum Park with the Bean, fountains, walk along the bridge to the lake front. Enjoy the view and return.

Depending on what day of the week, you could be through immigration and customs sooner than later. Passenger loads have started to go down from what I'm seeing and I'm not hearing about the long queues anymore as often.

Rush hour, I'd go Blue line over a cab going in, but late at night there's no reason you couldn't cab it back to the ORD hilton to save time.

May I ask what flight and day you're arriving on?

Agree with this. ^

After Mil Park and the the Lakefront, the OP could walk back towards Mich Ave and stop at Tavern at the Park for dinner (on Randolph and Mich Ave - north edge of Millennium Park), then take a nice walk up Mich Ave, and end the night with a drink or two in the River North or Gold Coast neighborhoods.

And while I'd train down to the Loop, I'd probably spring for a cab back to the hotel after a long day of flying and sightseeing. (Approx $40).