Are those tickets refundable? I don't want to burst your bubble, but I did that trip in my mid-20s (which I was used to hostels and cheap travel), and it was not a pleasant trip.

We are headed to Chicago in July...had a hard time finding reasonable airline tickets so we ended up buying train tickets: $400 total for a family of four. It's an overnight trip (leave late afternoon after the next morning) and it will be the kids first train trip so we are all looking forward to it (although we didn't book a sleeping cabin so we may not be quite as happy the next morning

Just another option to consider.

I'm guessing lots of busy/desirable-location destinations are expensive right now bc gas is so expensive. I bought DCA to ORD well in advance for a June trip and we got $290, but we are also able to fly off peak days and times. Fri-sun always seems more.

Agree with the pp's that airfare to Chicago is really expensive right now. I was able to get 20,000 mile flights.

Yeah, that's a great price. I usually do DCA - ORD, but MDW works for me too. I will have to sign up for the Southwest emails to see if I can get a deal sometime.

It was a 69$/way sale on southwest from iad to mdw. Right now southwest is not cheap at all but we do have points so we will probably end up on them even if they still have the highest prices.

Wow, $140?! I was happy to pay $280 for Easter. What airline/airports?

We fly to Chicago twice a year, including this past January for 140$. The flights for this summer are absolutely ludicrous. I am trying to go in July and they are all over 300$ no matter the airport or airline. I am still holding out on purchasing for another month or so to see if flights go on sale, but not that hopeful...

BWI to Midway on SW is also an option.

We flew Dulles to Midway last weekend for $284 on Southwest.

I'd like to spend a June weekend in Chicago. I'm having trouble finding flights under $340. Any suggestions?