United Kingdom to Chicago in May - travel advice

[Thoric]

Most viewers of this forum as American, I guess, so it's a good place to ask for some quick advice on travelling to Chicago.

It looks like I'll be working in Chicago for about a week from 19th May, so I'm looking for flights, accommodation advice etc.

Using SkyScanner.com, it seems direct flights are about £580 ($960) return, when flying Sun to Sat. Does anyone have any advice on better ways to travel - for example, is it cheaper if I avoid weekend flying, or is it cheaper if I book the hotel along with the flight (like a package deal), or is it cheaper if I etc. etc. I could spend all day trying different permutations and not get the right formula! 

Any advice greatly welcome    

[Intaris]

All I know is don't ask for what you most likely classify as "pizza" (thin base) in Chicago.  They have mostly deep-pan pizza there.

Yes, Jon Stewart and Stephen Colbert are my references.

[thoult]

I know it's a PITA for those with families, but if you can include a Saturday stay then flight prices usually drop. That's offset against your hotel, food, car costs, naturally.

Also, one stop flights, whilst they're often a pain, don't have to be that bad. Pretty sure Aer Lingus can get you there with a brief sojourn in Dublin. Alternatively, you could fly to New York and then on to Chicago - there are usually cheap flight deals to JFK or Newark kicking around, and that plus an internal flight will probably still come out cheaper.

[Thoric]

Thanks thoult.

Which aspect exactly is a pain for those with families? I ask becuase I was considering bringing my wife along as this trip overlaps with our wedding anniversay (ouch) and she just loves America, so was thinking about scrapping the money together for flight tickets for her as a gift. If you mean Chicago is depressing and not tourist friendly then I'll forget that idea!

[Darin.K]

London and O'Hare are major United hubs, usually means plenty of flights. Saturday night stays are pretty much relics at this point, they used to be a pain for families of business travelers since it meant staying away for a weekend. Red-eyes used to be cheaper, not so much these days. Quite often they are desired it seems.

Want cheaper flights, ask what a business traveler would do and do not do that. This means do not try to arrive Monday morning nor leave Friday during the day. Do not buy a refundable ticket or buy on short notice.

Ask what a family would do and do not do that. This means try to avoid the late morning flights since no one gets the kids up at 4 am the families travel early in the day but not too early. Fridays and Sundays are often tight.

Having logged way too many miles, my advice is not to skimp too much on the flights. It is worth a few quid to not be as jet lagged or stuck in some random airport because the 1 stop flight was a bit cheaper.

Hotwire has done very well by me for renting cars and finding hotels when I have no preference. It gave me a much better deal at NI week than the official hotels. The last six or seven times at ORD it put me in Avis, might be a trend. If you do not need a car, I splurge for a cab on arrival since I can walk straight from the gate after a long flight. I will then take a scheduled van back to the airport.

[thoult]

Thoric - as Darin says, business flyers tend to try to avoid weekend stays so they can be home with families. But if you're taking your other half with you, then it's not so much of a problem!

Darin - the Saturday night stay is still essentially the Monday to Friday business traveller / weekend family flyer advice combined.

Thoric - what about flying to Milwaukee and then driving the ~106 miles to Chicago. At night. Wearing sunglasses.

[Thoric]

Thanks guys, that's all great advice.
I checked out Milwaukee but it takes two stops and costs a bit more than direct to Chicago, but nice idea. I've certainly got no problem driving on the wrong side lol 🙂

[thoult]

https://www.youtube.com/watch?v=gvKs2VLmVnY

Wasn't a serious suggestion! 😄

[Thoric]

Ha ha. I see 

I'm not familiar with Blues Brothers I'm afraid 

[taper]

To me Chicago is the definition of "Nice place to visit but I wouldn't want to live there."

Plenty of family activities.  The Adler planetarium, Shedd aquarium, and Field Museum are right next to each other, and the Science and Industry museum a little further south.  Lots of neat architecture, old and new.  Willis(Sears) Tower has an observation deck but the Hancock tower is actually better.  Various pro sports stadiums.  Great food.

Now the bad.  O'Hare airport becomes a disaster if a storm comes through.  In the winter you can be delayed literally for days.  May shouldn't be as bad but leave plenty of time to make connecting flights.  Chicago has a high crime rate but it's really only a problem in certain areas.  Stay in the tourist spots and you'll be fine any time of day.  Do NOT wander around without knowing where you're going.