Need help with a 2 day layover in Chicago. Possible?
 

I leave from SFO on 10/16 and I planned to be at Chicago for 2 days and then I have a business trip to Green Bay. So I have to leave Chicago on 10/18 to Green Bay. I'd like to return from GRB to SFO on 10/20.

If I book a round trip like this: SFO-ORD-GRB-ORD-SFO, will I be able to stay for Chicago for 2 days before taking a flight from ORD to GRB?

Since my business trip to Green Bay happens to be on 10/19, I don't know how to make a reservation?

Anything over 24 hours is a stopover, not a layover. You just need to use the UA website's multi-city routing tool. It's worked like a charm for me when I've priced out moderately complex itineraries like yours.

Alternatively, you could book two separate, nested round-trips, one SFO<>ORD and one ORD<>GRB. Might even be cheaper.

ORD-GRB round trip is costing me >$1035. Multi segment might work.

When doing this book SFO-ORD first, and then wait a few day to book ORD-GRB. Give yourself some plausible deniability.


SunLover

Driving MKE to GRB takes about 2-ish hours up the lake on I-43 and about the same on I-41. Ticket prices tend to be cheaper with more options out MKE as well (same with rentals.) Also, ATW is only about 30 minutes drive, and sometimes has better flight options.

Multi segment booking worked out great for $578. Thanks all.