Airfare to Italy July 2019 from Chicago

I would set up a kayak alert to send you every day for your flights. I have had one up for 1.5 years, and I finally got the dates and price to where I want them, so I bought a RT from Atlanta for $548! Chicago is a popular airport for Europe trips (when I lived in Italy, I took half of my flights through there), so I don't doubt that they COULD go down.

I am sorry I don't know what the best prices are for Chicago, but Kayak could help. I looked at my flights today (I was looking up seatguru stuff) and the same flights were $1880! I have seen a lot of variation in prices, so I would start looking now and jump when you see a good price.

Fares are utterly unpredictable (by me, at least), but they do tend to bounce around a lot. In addition to a fare alert (I use Google Flights), with five tickets needed I would be checking every day manually. There's too much money on the line not to do that. I've done such monitoring for my last two trips, and for this year's central-Europe itinerary the fare for Washington DC-Munich / London-Washington DC repeatedly bounced between $800+ and $1300+. Pay particular attention between now and Thanksgiving, including during holiday weeks. I think there's a good chance you'll see an opportunity to beat the $1400 fare by quite a lot. Obviously, I cannot guarantee it.

One thing I've observed is that when you're looking for a non-stop flight on a route that often requires a connection (as I assume Chicago-Rome does), you don't want to be shopping for flights only one or two months before the trip. There may still be some decent fares on connecting flights at that point, but often by that time all the non-stops are up in the price range you are currently seeing, or even higher.

You haven't specified your planned arrival and departure points in Italy (or your specific travel dates). You don't necessarily have to fly in and out of the same city. You might be able to do Rome/Milan or Milan/Rome for the same price as a round-trip to either of those cities. That's what the websites call a "multi-city" flight. You can also look at Venice/Rome or Rome/Venice--depending on where you plan to go in Italy, of course. From my origin, Milan and Rome are often the same price, but that is highly origin-dependent, and it may not work out that way for you.

Also be aware that Italy can be miserably hot in July. That would be a greater concern for me than the crowds. It is a serious consideration if your parents are elderly. Be sure your hotels are well air-conditioned and conveniently located for taking afternoon breaks. If you have the time to do so and your parents don't have serious mobility issues, I'd consider spending a few days up in the Dolomites in a place like Ortisei. You'll be nearly certain of having pleasant temperatures there because of the altitude, whereas the rest of the country may be miserable. It's a lovely area, and there are easy walks in high-mountain meadows as well as more challenging options.

Well you have now learned the most valuable lesson--whenever a good fare appears for a good schedule, no matter how early, grab it! But at least you get to say I told you so, which can be fun.
For a July trip, I would be thrilled with anything in the 1000-1500 range, but you are very likely to snag a sale, just start monitoring as others suggested. Do be sure to check multi-city flights if it works for your itinerary, as it can save a ton of time are not necessarily be any more expensive.
I travel in late May from the east coast, but I am very particular about my layovers and schedules. The best deal I ever snagged was around 800 (but by the time we paid for seat selection, etc., closer to 1000).

hey gina
I agree with others. I do fare alerts with kayak and another, but look everyday also. when you see something, look at multi-city (into one city out of another-no backtracking), arrival times, because of hotel/apt checkin and departure times, super early mornings, check airlines if same fare and book it. No looking back. Get guidebook where you want to go and see, train schedules and specials, then hotels/apts book early. It is high season, maybe cheap fare but expensive lodging. Lots of research for you. Come back to forum for more suggestions. Like others say, the heat in summer, so maybe northern Italy. Good luck
aloha

Thanks all for your help... We will be flying into Rome and out of Venice. I don't want to do any backtracking... Thankfully my parents are in very good shape and I believe are part lizard.. They love hot steamy warm weather...BLAHHH..lol but I will definitely make sure all of our hotels have air conditioning. I have already signed up for kayak and I now check 3 times a day...lol

You have plenty of time to buy these tickets. Do not get spooked by a single data point (price increase from one amount to another). This is like stock - it goes up and down....many, many, many times. You have to monitor prices over several months to get an idea of what's "good". There is no need whatsoever to panic this early. July is peak season so probably something in the $900-$1,000 range is not out of the question. Watch for sales and also consider budget carriers. By the way, if you have some patience, Turkish Air is excellent as far as prices go, but there is a stopover in Istanbul as part of the deal. I've done it several times.

To where in Italy? You need to know which airports in Italy work for your first Italian destination and your last. Flights landing or departing near your destinations will save you time as well as transport and perhaps hotel costs versus a flight to or from a lower cost gateway like Milan or Rome. You should set multiple alerts for different cities that work for your trip.

Gina!

Here's what we did out of O'Hare in March 2017...

Started looking in about October 2016, had two different itineraries for specific dates and we were going to go wherever was cheaper. Had alerts on both Kayak and Google. Finally zeroed in on a Chicago/Frankfort/Rome outbound, and a Naples/Munich/Chicago inbound, with Lufthansa. Price had started out around $1300 R/T, kept dropping, dropping, until we finally fired in at $890, I want to say early December 2016. Damned if it didn't drop to $770 the next day, then immediately shot up over $1000 again.

We were pretty happy with our choice but just like stocks, you probably won't get in at the bottom. You just don't want to enter at the top.

Enjoy your planning!

Gina -

Certainly feel your pain. We are flying into Venice and out of Rome next September so we are in the same predicament as to when to pull the trigger on a flight. Would agree with the other posters here on setting up a Kayak alert on the flights you are looking at. We have had good luck also with skiplagged.com to find reasonable flight prices along with some airlines that Kayak and some of the others may not pull up. Not sure of your specific dates you are flying to Rome but in looking at Saturday, July 13th flights to Rome start at $684. I would go there and you can filter your search with number of stops, etc. that is going to fit your needs.

Are you going to be booking hotels for your trip, too? We were in the same situation - family of 4, going to Italy July 2019 (flying into Venice and out of Rome). The flights I was looking at on Delta were around $1,450/person. I had a travel agent check on prices - and when she booked hotels for us (1 night in Venice pre-cruise and 4 nights in Rome for later in the trip) she was able to get us the 4 flights, a family suite in Venice for 1 night and TWO hotel rooms in Rome for 4 nights for a total of $5,800 which was less than I was finding for JUST the flights!

Gina,

The more you check the fares on your computer(s), the more the airlines and on-line travel agents track you and tailor their offerings to maximize their revenue (i.e. present higher prices). To combat this, clear your browser history and cookies between searches.

Since you are traveling as part of a larger and diverse group of people, I would not place ticket price as the most important determining factor. Different airlines use different European hubs as their transfer ports. American and British Airways generally use Heathrow while United/Lufthansa generally use Frankfurt and Delta partners with Air France and KLM so Paris and Amsterdam are used. While direct flights from the USA are available, they are generally seasonal and usually operate out of an east coast hub (Phily, New York, etc.). These direct flights also usually come with a cost premium.

From personal experience, if anyone in your party requires any sort of special assistance at the airport, I would avoid Heathrow. Unless you are on BA operated flights on both legs, you will most likely have to change terminals. If you arrive on an AA flight, you'll come into terminal 3 and more than likely depart out of terminal 5 which normally means a bus ride across the airport. Plus, their 'special' passenger assistance service is really sub-par. Also, when it comes to London, ensure you are arriving and departing out of the same airport. BA operates out of three on the regions airports and AA will often pair up flights operating out different airports. (The same holds true for flying into/out of New York.)

I've been looking at flying Chicago to Rome on Iberia (a sister to BA under the International Airline Group). Earn and use AA miles with a direct flight to Madrid and easy connections to elsewhere in Europe. Their long-haul flights arrive at a satellite terminal and connecting flights depart out of the main terminal (connected by underground people-mover) but the airport advertises an easy 20-30 minute transfer coming from the USA and departing to elsewhere in Europe.

My wife and I are headed out June 13 and returning July 7, 2019 to celebrate our 30th. We are tracking a BA non-stop from New Orleans to London (8h 50m) for 3-4 days, then London to Venice, and out of Milan home. Milan to New Orleans is on American, with a 5 hour lay-over in Miami. I got stuck with that trying to avoid more than 1 stop on the way home. We are booking "premium economy" for the transatlantic flights (which is only a couple of hundred dollars more than basic economy). At present this "open-jaw" trip is $2,322 each. Booking everything through the BA site seems the least trouble, and gives us the same baggage allowance all the way through. I'll keep watching, but I suspect I'll be buying between Christmas and the New Year.

Richarde99, have you tried pricing the middle leg of your trip separately so you can take advantage of a budget-airline ticket between London and Venice?

acraven Thank you for the idea. I priced New Orleans to London, then Milan to New Orleans, it ended up BA out and American return (same flight times) ($4,234). Then I found an Easy Jet from London (Gatwick) to Venice ($83). Turns out to be $4,317 or $2,158 each. Savings are $164 each. The hold bag fee is $40 pr 23 Kgs. so add back $80. Still a savings! I think the primary cost is the non-stop flight from New Orleans, it's at a premium. I'm going to look at other options and see if there is a significant savings.

Yes, I think New Orleans is killing you. If you weren't interested in premium economy, I'd say you have a lot of time and might get lucky and catch a significant price dip in the next few months, but I've read a lot of comments on this forum about needing to buy early to get reasonable fares for premium economy seats (which I've never bought), so I just don't know how much time you have.

One other thing: I'm not sure the budget airlines have all their July 2019 flights loaded yet.

acraven -- I priced the same trip in "standard" economy from New Orleans and only saved $200 each ticket same "open-jaw." I then priced the same route out of Houston, Atlanta, and Charlotte, and saved perhaps $250 each, but I didn't bother to check the flights in and out. The bottom like is that I'm paying a premium for the non-stop transatlantic flights, a bit more for the extra leg room.

Try using skyscanner.ca.

I punched in 5 persons and got the following:
July 8 ORD - FCO 11 hours 1 stop Swiss Air
July 22 VCE - ORD 12.5 hrs 1 stop Swiss Air
$888 pp booking thru Fareboom was the cheapest. There are other options.

I have never used Fareboom.

If you can, consider reversing trip ie fly in to Venice and fly out of Rome. It may be cheaper. Also, i have found in past renting a car in Venice and dropping off in Rome is much cheaper than the reverse.

I subscribe to Scott's Cheap Flights and let him do the dirty work for me. I'm surprised this wasn't mentioned (although I did only a brief scan.)

It's a little too early for July, I'd wait a few months. I'm currently watching for fares to Puglia in April and it's still a bit early. I can tell I'm getting close though.

My gut tells me you shouldn't have to pay more than $800 and you could very well find it in the $600s.

I was in the same situation as you trying to book Seattle/Florence tickets for July. I saw reasonable prices (<$1,000) several times when I first checked, but when I was ready to purchase, they had gone up by about $600 per ticket. I was able to get RT tickets to Milan (which actually works out well for our itinerary) for about $940 and purchased a ticket for another family member to fly into Milan and home to Seattle from Venice for a little over $900. Of the destinations I checked, Florence was by far more expensive than Rome, Milan or Venice.

I am also checking on flights for an east coast family member to join us and as of last week fares out of NY and DC are still extremely high. It made me wonder if there is a big regional difference in timing for best international fares.

British Airways offers a 72 hour hold option for just $10/passenger which is refunded if you book. The tickets I purchased stayed the same price over the three days.

Clear your cookies and browse incognito. Otherwise, the flight search servers are on to your plans and the fares will jump the next time you search. Probably what happened to you when you searched the second time.

Would definitely recommend Scott's Cheap Flights if you have some flexibility on your schedule. You pay a yearly fee to join but it may be worth it for you on this trip or for trips in the future.

Post Script: We ended up purchasing our open jaw tickets on the 18th. The prices bounced between $4,100 and $5,600. Ended up at $4,800 and we were ready to buy, but checked pushing back our trip one week, and the fare dropped by $600. So, 2 tickets for $4,212 from New Orleans to London premium economy (non-stop) on June 20, London to Milan economy on June 26, and Venice to New Orleans premium economy (1 1/2 hrs in Chicago) on July 14. Booked it all direct on British Airways site, the return leg is on their 'partner' American Airlines. The exact same flights in economy would have been $3,873. I completely agree with those commentators who said buy them when you find a good price, the problem is that it takes some time of following before you find out what a good price might be. FWIW Last year we flew American Airlines from New Orleans to Charlotte for a 3 1/2 hour layover, then to Paris; flew Air France to Rome, and home on American Rome to Charlotte to New Orleans. All economy and it was about $600 less, per ticket.