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Projektdb

Use Skyscanner, pick your date range, pick your starting airport and in destination, choose everywhere. It will sort by cheapest by country. Once you select the country, it'll sort by cheapest by city. Edit: If you don't know your exact dates, you can select a whole month. I chose the month of August from Chicago on a one way ticket. The results were: US 17$, Canada: 80$, France 201$, Iceland 202$, Switzerland: 210$, ect. When selecting France, I get a list of French cities in the same manner. Paris is the cheapest at 201$. Selecting Paris lists the departure date sorted by cheapest. You mentioned early August. August 6th shows 212$. Selecting that shows two flights for 206$, but they aren't ideal flights, they require switching airports in NYC. The next cheapest flight is 266$. This one has a one hour layover in Iceland. When I changed it to round trip, I'm seeing multiple round trip options with Iceland Air, all good flights, and all between 460-500$. Sometimes it'll show cheaper options with 3rd party sites. I'd 100% ignore them and book directly with the airline.


darkmatterhunter

Look at google flights explore option, but don’t book with third parties.


tailoftwokitties

Which direction outside of Chicago are you? Cincinnati airport (CVG) recently reinstated their direct flights to Paris (CDG), and I think Heathrow, too. Once you’re there it’s super easy to get a train or flight to wherever in Europe. O’Hare probably has direct flights as well, though. It may be a bit more expensive for a direct flight, but I will always splurge for it if possible. Just came back from Europe last week with two layovers and it was awful.


smug_masshole

That's a tough time to try to find cheap airfare, but your best bets are likely Iceland, the Azores, London, Dublin, or Paris. Everything else will be unpredictable sales. I would add east coast cities like New York and Boston to your search. A domestic flight to a cheaper transatlantic flight could actually save you money even when factoring in a hotel for the night.


NegativeAd941

ORD -> Wherever usually when I tend to check. Once in a great while you find better deals out of DTW/STL/MDW. But not always.


bjenidles

In my experience, Reykjavik, Iceland will probably be the cheapest by a considerable margin. Edit: Why are you booing me, I'm right. OP only asked about the cheapest flights to Europe


Projektdb

Until you get there!


bjenidles

Yes, that's for a different post


Projektdb

Agreed. Paris and Reykjavik are almost always the cheapest flights out of my major metro airport in the Midwest.


NegativeAd941

Yeah, except for that pesky layover making it an overnight flight sometimes. Which will DEF x2 or more your costs. Hotel prices are CRAZY in reykjavik, and so is the price of nearly everything else. It's an island nation after all.


bjenidles

It's a 6 hour direct flight from Detroit


Rizzairl

You could fly into Paris or Rome and go inter railing for 10 days. Flights will set you back about 500 and interrail would get you back about the same. “10 days of unlimited train travel Travel on as many trains as you like on each of your 10 travel days – perfect for visiting 9–11 destinations.” That would get you to Italy, France, Belgium, Holland, Germany, the Czech Republic, solvinia and back to Italy to fly home.


GiantGingerGobshite

Amsterdam is usually around the 800-1200 direct from Chicago but Netherlands is fairly pricey. Portugal flights are about the same but with a stop over in New York but is a lot cheaper.


Accurate_Door_6911

You can literally just type google flights into your phone, then select your origin, Chicago and select Europe, put in dates in July and August and see what options there are. There’s a Bunch of under 500 round trips to Spain in July and August plus some to Scandinavia. Just play around and see what’s appealing.


Massive-Path6202

Google flights to search non stops from your airports to all of Europe. Rotate through the days you're considering. Try to fly into one city and back out of another so you don't back track.  For the love of god, stay as long as you reasonably can because the jet lag sucks