$226 Cheap Delta flights from Lexington to Chicago (LEX to MDW)

Find The Best Day To Fly from Lexington to Chicago

Amazing Delta LEX to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $209 round trip and $226 one way. Prices and availability subject to change. Additional terms may apply.

Tue, Aug 19 - Sat, Aug 23
LEX
Lexington
MDW
Chicago
$209 Roundtrip, found 4 days ago
$209
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 19 from Lexington to Chicago, returning Sat, Aug 23, priced at $209 found 4 days ago
Sat, Aug 9 - Sat, Aug 16
LEX
Lexington
MDW
Chicago
$210 Roundtrip, found 11 hours ago
$210
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Aug 9 from Lexington to Chicago, returning Sat, Aug 16, priced at $210 found 11 hours ago
Sat, Aug 16 - Sat, Aug 23
LEX
Lexington
MDW
Chicago
$212 Roundtrip, found 4 days ago
$212
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Aug 16 from Lexington to Chicago, returning Sat, Aug 23, priced at $212 found 4 days ago
Wed, Oct 22 - Sat, Oct 25
LEX
Lexington
MDW
Chicago
$222 Roundtrip, found 6 hours ago
$222
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Oct 22 from Lexington to Chicago, returning Sat, Oct 25, priced at $222 found 6 hours ago
Tue, Jul 29 - Tue, Aug 19
LEX
Lexington
MDW
Chicago
$228 Roundtrip, found 3 days ago
$228
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jul 29 from Lexington to Chicago, returning Tue, Aug 19, priced at $228 found 3 days ago
Tue, Aug 19 - Sun, Aug 24
LEX
Lexington
MDW
Chicago
$234 Roundtrip, found 4 days ago
$234
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 19 from Lexington to Chicago, returning Sun, Aug 24, priced at $234 found 4 days ago

MDW From LEX Economy Coach Packages on Similar Airlines

Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Lexington (LEX) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Lexington (LEX) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Lexington (LEX) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from Blue Grass to Midway Intl.
View all trips

Travelers ❤️ these 🏨 after their flight to Chicago

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
8.8/10 Excellent! (1,265 reviews)
"Excellent stay"

Reviewed on Jul 15, 2025

Crowne Plaza Chicago West Loop by IHG
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! (8,979 reviews)
"Amazing views and Chicago trip was over the top!!"

Reviewed on Jul 15, 2025

Congress Plaza Hotel
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

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 ...
8.2/10 Very Good! (1,001 reviews)
"Its was very nice and pleasant stay"

Reviewed on Jul 15, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
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.