$307 Cheap Delta flights from Key West to Chicago (EYW to MDW)

Find The Best Day To Fly from Key West to Chicago

Amazing Delta EYW to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $370 round trip and $307 one way. Prices and availability subject to change. Additional terms may apply.

Discover our best Delta flight from Key West EYW to Chicago MDW 

To find the best deals on flights to Key West from Chicago with Delta, just enter your travel dates, filter by Delta, and hit search. You’ll find flights to choose from and can sort by price, flight duration, and arrival or departure time.  

 

Return flights from Key West EYW to Chicago MDW with Delta 

If you’re planning a round trip, booking return flights with Delta is usually the most cost-effective option. With airfares ranging from $370 to $490, it’s easy to find a flight that suits your budget. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way Delta flights from Key West EYW to Chicago MDW 

A one-way ticket gives you much greater flexibility—allowing you to choose your return date, destination, and time whenever you’re ready. By booking in advance you can find great deals on one-way tickets too. Right now, a one-way Delta flight from Key West to Chicago costs from $307. Prices and availability subject to change. Additional terms may apply. 

 

The easy way to find cheap flights to Chicago MDW from  Key West EYW with Delta 

To find a cheap Delta flight from Key West EYW to Chicago MDW, sort your search results by price or filter by budget. Thanks to Travelocity’s Price Match Promise, if you find a better airfare deal anywhere else within 24 hours, we’ll credit or refund the difference. 

 

How to find our best airfare deals on Delta flights from Key West EYW to Chicago MDW 

If you’re looking for cheap flights, it helps to be flexible when it comes to your travel dates. You’ll usually find lower cost tickets when you travel during quieter months such as March, or if you book a flight with a stopover. 

 

Find nonstop flights from Key West EYW to Chicago MDW with Delta 

If you’re keen to be on Chicago soil fast, don’t waste time with a stopover—filter your search results to show direct Delta flights only. The journey takes around hour(s) min(s) – so you’ll be there before you know it. 

 

Flexible airline tickets for Delta flights from Key West EYW to Chicago MDW 

Make sure you’re not out of pocket if plans change by choosing a flexible ticket with penalty-free amendment and cancellation options. Use our ‘no change fee’ filter to see which flights have this option.  

 

There are a lot of reasons to book your flights to Chicago MDW from  Key West EYW with Delta on Travelocity 

At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether you’re traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.

Delta Airports
Hop on a(n) Delta flight today by flying to many destinations out of these domestic and international airports:
Airport code
Country
Airport name
Number of flights
ATLUSAHartsfield-Jackson Atlanta Intl.252
DTWUSADetroit Metropolitan Wayne County156
MSPUSAMinneapolis - St. Paul Intl.131
SLCUSASalt Lake City Intl.116
SEAUSASeattle - Tacoma Intl.57
LAXUSALos Angeles Intl.41
AMSNLDSchiphol31
YYCCANCalgary Intl.26
YYZCANPearson Intl.24
JFKUSAJohn F. Kennedy Intl.23

Travelers ❤️ these 🏨 after their flight to Chicago

Holiday Inn & Suites Chicago - Downtown, an IHG Hotel
Holiday Inn & Suites Chicago - Downtown, an IHG Hotel
3 out of 5
506 West Harrison Street, Chicago, IL
A 24-hour gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 ...
8/10 Very Good! (1,002 reviews)
"Right off the highway, very clean inside. Great rooms for the price and right near where we needed to be."

Reviewed on Feb 19, 2025

Holiday Inn & Suites Chicago - Downtown, an IHG Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center ...
7.8/10 Good! (8,511 reviews)
"A comfortable historical hotel, enjoyed the bar area, cocktails were good , would not recommend dining at the hotel. On Expedia it says it has parking and in and out privileges but this is not true, once you park you cant leave unless paying again (62$) . Had a paranormal experience in room 917 so ..."

Reviewed on Feb 18, 2025

Congress Plaza Hotel
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...
8.2/10 Very Good! (1,665 reviews)
"Beautiful hotel in the perfect area"

Reviewed on Feb 18, 2025

Hilton Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.