Cheap flights from EVV to MDW (Evansville Regional to Midway Intl.)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights from EVV to MDW starting at $322 One Way, $588 Round Trip

Prices starting at $588 for return flights and $322 for one-way flights to Midway Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jun 9 - Wed, Jul 1
EVV
Evansville
MDW
Chicago
$588 Roundtrip, found 11 hours ago
$588
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Jun 9 from Evansville to Chicago, returning Wed, Jul 1, priced at $588 found 11 hours ago
Wed, Jun 10 - Wed, Jul 1
EVV
Evansville
MDW
Chicago
$670 Roundtrip, found 1 day ago
$670
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 10 from Evansville to Chicago, returning Wed, Jul 1, priced at $670 found 1 day ago
Tue, Jun 9 - Wed, Jul 1
EVV
Evansville
MDW
Chicago
$711 Roundtrip, found 11 hours ago
$711
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Jun 9 from Evansville to Chicago, returning Wed, Jul 1, priced at $711 found 11 hours ago
Tue, Jun 9 - Wed, Jul 1
EVV
Evansville
MDW
Chicago
$721 Roundtrip, found 11 hours ago
$721
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Jun 9 from Evansville to Chicago, returning Wed, Jul 1, priced at $721 found 11 hours ago
Tue, Jun 9 - Wed, Jul 1
EVV
Evansville
MDW
Chicago
$742 Roundtrip, found 1 day ago
$742
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 9 from Evansville to Chicago, returning Wed, Jul 1, priced at $742 found 1 day ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$128 nightly
The price is $151 total per night from Apr 26 to Apr 27
$151 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,001 reviews)
Breakfast was average. Breakfast is only included for two guest.

Reviewed on Apr 13, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
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
$135 nightly
The price is $158 total per night from Apr 26 to Apr 27
$158 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
9/10 Wonderful! (2,093 reviews)
No coffee in coffee pot no breakfast

Reviewed on Apr 16, 2026

Crowne Plaza Chicago West Loop by IHG
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
$118 nightly
The price is $139 total per night from Apr 26 to Apr 27
$139 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,943 reviews)
Clean room | Staff | Breakfast | Air conditioning

Reviewed on Apr 16, 2026

Hilton Garden Inn Chicago Downtown South Loop
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.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$116 nightly
The price is $137 total per night from Apr 26 to Apr 27
$137 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,157 reviews)
Clean room, uncomfortable bathtub, cheap amenities- heater was broken in room. Light in bathroom dim. Maintenance staff was nice and things are very clean, but won’t be staying here again.

Reviewed on Apr 16, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$119 nightly
The price is $140 total per night from Apr 26 to Apr 27
$140 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (4,131 reviews)
Great location. Clean rooms. Helpful staff

Reviewed on Apr 16, 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
$139 nightly
The price is $163 total per night from Apr 26 to Apr 27
$163 total
Apr 26 - Apr 27
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,847 reviews)
They didn’t clean our room even when I requested to be cleaned and we had to go and request towels and paper, breakfast is not good at all.

Reviewed on Apr 16, 2026

Embassy Suites by Hilton Chicago Downtown River North
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.

Chicago Hotels With Airport Transportation

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave Elk Grove Village IL
$55 nightly
The price is $62 total per night from Apr 22 to Apr 23
$62 total
Apr 22 - Apr 23
Total with taxes and fees
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,923 reviews)
Perfecto

Reviewed on Apr 13, 2026

Motel 6 Elk Grove Village, IL - O'Hare
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
777 E Grand Avenue Bensenville IL
$91 nightly
The price is $101 total per night from May 6 to May 7
$101 total
May 6 - May 7
Total with taxes and fees
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.4/10 Good! (1,361 reviews)
Rehman who was in front desk was so nice and excellent in what he does and keep the guest comfortable

Reviewed on Apr 15, 2026

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
$78 nightly
The price is $90 total per night from Apr 22 to Apr 23
$90 total
Apr 22 - Apr 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8/10 Very Good! (2,986 reviews)
Everything was abovevand beyond. Zero complications or complaints.

Reviewed on Apr 16, 2026

Comfort Suites Chicago O'Hare Airport
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.

Low Priced Chicago Hotels

Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
$91 nightly
The price is $106 total per night from Apr 27 to Apr 28
$106 total
Apr 27 - Apr 28
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (2,874 reviews)
The Lounge was very good.

Reviewed on Apr 15, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$118 nightly
The price is $139 total per night from Apr 26 to Apr 27
$139 total
Apr 26 - Apr 27
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7.4/10 Good! (2,564 reviews)
Room was clean, staff was friendly. They've been remodeling and the place looks good

Reviewed on Apr 15, 2026

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave Elk Grove Village IL
$55 nightly
The price is $62 total per night from Apr 22 to Apr 23
$62 total
Apr 22 - Apr 23
Total with taxes and fees
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,923 reviews)
Perfecto

Reviewed on Apr 13, 2026

Motel 6 Elk Grove Village, IL - O'Hare
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.

Family Friendly Hotels in Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
511 North Columbus Drive Chicago IL
$164 nightly
The price is $192 total per night from Apr 26 to Apr 27
$192 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (2,807 reviews)
The breakfast was disappointing. Very crowded, long lines and few choices

Reviewed on Apr 16, 2026

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
$184 nightly
The price is $214 total per night from May 8 to May 9
$214 total
May 8 - May 9
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,394 reviews)
The hotel is beautiful. The room was clean and furnishings newer. There are a lot of rooms so you could be placed far away from the elevator. For us that was not an issue but I could see it being so for others.

Reviewed on Apr 14, 2026

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
$139 nightly
The price is $163 total per night from Apr 26 to Apr 27
$163 total
Apr 26 - Apr 27
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,847 reviews)
They didn’t clean our room even when I requested to be cleaned and we had to go and request towels and paper, breakfast is not good at all.

Reviewed on Apr 16, 2026

Embassy Suites by Hilton Chicago Downtown River North
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.

EVV to MDW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date

Frequently asked questions

Are there non-stop flights from Evansville Regional Airport to Midway Airport?
As you can't fly directly from Evansville Regional Airport (EVV) to MDW at this point in time, a flight with just one stopover is the next best thing. Delta Air Lines, KLM and Aeromexico are all reputable airlines that operate on this route.
What is the shortest flight from Evansville Regional Airport to Chicago Airport?
Order an in-flight wine and get comfortable in your seat with a fascinating movie or book. With the journey from Evansville Regional Airport to MDW taking 3 hours and 23 minutes, there's plenty of time to sit back and enjoy the ride.
How many hours flight from EVV to Midway Airport?
It typically takes about 3 hours and 29 minutes to journey from Evansville Regional Airport (EVV) to Chicago Airport. You'll be in your seat for quite some time, so think about bringing some entertainment, like an audiobook or some movies.
What airlines have the most flights from Evansville Regional Airport to Chicago Airport?
At the moment, you can't fly nonstop from Evansville Regional Airport (EVV) to MDW. However, you will be able to book flights with one or more stops. Look on the bright side — use the time to stretch your tired legs or grab a decent coffee!

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.