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Cheap Flights from Stuttgart (STR) to Chicago Midway (MDW)

Compare Stuttgart to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Stuttgart to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Stuttgart to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.£420 per passenger.Departing Mon, 2 Mar, returning Mon, 16 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Stuttgart on Mon, 2 Mar, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 16 Mar, arriving in Stuttgart.Price includes taxes and charges.From £420, select.
Chicago.£422 per passenger.Departing Sat, 18 Apr, returning Tue, 28 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Stuttgart on Sat, 18 Apr, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 28 Apr, arriving in Stuttgart.Price includes taxes and charges.From £422, select.
Chicago.£508 per passenger.Departing Wed, 6 May, returning Sun, 10 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Stuttgart on Wed, 6 May, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 10 May, arriving in Stuttgart.Price includes taxes and charges.From £508, select.
Chicago.£508 per passenger.Departing Wed, 29 Apr, returning Sun, 10 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Stuttgart on Wed, 29 Apr, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 10 May, arriving in Stuttgart.Price includes taxes and charges.From £508, select.
Chicago.£513 per passenger.Departing Wed, 25 Mar, returning Wed, 1 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Stuttgart on Wed, 25 Mar, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Wed, 1 Apr, arriving in Stuttgart.Price includes taxes and charges.From £513, select.
Chicago.£623 per passenger.Departing Tue, 24 Feb, returning Tue, 10 Mar.Return flight with Eurowings and Frontier Airlines.Outbound indirect flight with Eurowings, departs from Stuttgart on Tue, 24 Feb, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 10 Mar, arriving in Stuttgart.Price includes taxes and charges.From £623, select.
Chicago.£905 per passenger.Departing Tue, 11 Aug, returning Wed, 2 Sep.Return flight with Condor.Outbound indirect flight with Condor, departs from Stuttgart on Tue, 11 Aug, arriving in Chicago Midway.Inbound indirect flight with Condor, departs from Chicago Midway on Wed, 2 Sep, arriving in Stuttgart.Price includes taxes and charges.From £905, select.
Chicago.£958 per passenger.Departing Thu, 8 Oct, returning Wed, 14 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Stuttgart on Thu, 8 Oct, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Wed, 14 Oct, arriving in Stuttgart.Price includes taxes and charges.From £958, select.

Find the cheapest month to fly from Stuttgart to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Stuttgart to Chicago Midway flights are currently cheapest in March.
Feb
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Mar
from £420
Apr
from £422
May
from £508
Jun
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Jul
from £1,141
Aug
from £984
Sep
from £1,136
Oct
from £958
Nov
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Dec
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Jan
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Stuttgart to Chicago Midway: Alternative routes

Compare routes from Stuttgart to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

9 miles from central Chicago
Closest
from £420
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Chicago O'Hare International

16 miles from central Chicago
Cheapest
from £415
Search flights

Chicago Dupage County

32 miles from central Chicago
Search flights

Chicago Rockford

78 miles from central Chicago
from £867
Search flights

Stuttgart to Chicago: Flight information

The things to know before you go.
Cheapest flight found£420
Cheapest month to flyMarch

Finding cheap flights from Stuttgart to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Stuttgart to Chicago Midway is £420. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Stuttgart to Chicago Midway. But we found flights with one or more stops from £420.
As of February 2026, there are no flights flying from Stuttgart to Chicago Midway.
The cheapest month to fly from Stuttgart to Chicago Midway is usually March.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Stuttgart Airport to Chicago Midway Airport on Monday, 2 March 2026.
No airlines currently offer direct flights between Stuttgart Airport and Chicago Midway Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Delta offers the cheapest flight tickets to Chicago Midway.

How to find cheap flights to Chicago (MDW) from Stuttgart (STR) in 2026

Looking for cheap tickets from Stuttgart to Chicago Midway? Return tickets start from £420 and one-way flights to Chicago Midway from Stuttgart start from £279


Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Stuttgart to Chicago Midway. And with us there are no hidden fees - what you see is what you pay.
  • Compare flight deals to Chicago from Stuttgart from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to Chicago start from £279 one-way.
  • Flex your dates to find the best STR-MDW ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago Midway from Stuttgart.
  • Set up a Price Alert. You can easily track the fare of your cheap Stuttgart-Chicago Midway flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Flexible on when you travel? The cheapest month to fly from Stuttgart to Chicago Midway is March.
  • Fly without stops. Only interested in direct flights between Stuttgart and Chicago Midway? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business class flights from Stuttgart and Chicago Midway. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Stuttgart to Chicago Midway flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.
  • Search for cheap flights regardless of where you are. To get the best flight booking experience when out and about, download the app and search for plane tickets between Stuttgart and Chicago Midway whenever you want.

Combine your flight to Chicago Midway from Stuttgart with hotels and car hire

Once you've secured your cheap flight ticket from Stuttgart to Chicago Midway, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.


Plan the rest of your trip from Stuttgart to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.