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

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Cheap Flights from EVV to MDW starting at $368 One Way, $591 Round Trip

Prices starting at $591 for return flights and $368 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.

Wed, Feb 24 - Fri, Apr 2
EVV
Evansville
MDW
Chicago
$591 Roundtrip, found 4 days ago
$591
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Feb 24 from Evansville to Chicago, returning Fri, Apr 2, priced at $591 found 4 days ago
Thu, Sep 17 - Sat, Sep 19
EVV
Evansville
MDW
Chicago
$757 Roundtrip, found 6 days ago
$757
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Sep 17 from Evansville to Chicago, returning Sat, Sep 19, priced at $757 found 6 days ago
Wed, Feb 24 - Fri, Apr 2
EVV
Evansville
MDW
Chicago
$781 Roundtrip, found 4 days ago
$781
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Feb 24 from Evansville to Chicago, returning Fri, Apr 2, priced at $781 found 4 days ago
Wed, Feb 24 - Fri, Apr 2
EVV
Evansville
MDW
Chicago
$801 Roundtrip, found 4 days ago
$801
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Feb 24 from Evansville to Chicago, returning Fri, Apr 2, priced at $801 found 4 days ago
Wed, Feb 24 - Fri, Apr 2
EVV
Evansville
MDW
Chicago
$881 Roundtrip, found 4 days ago
$881
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Feb 24 from Evansville to Chicago, returning Fri, Apr 2, priced at $881 found 4 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
$162 nightly
The price is $188 total per night from Sep 27 to Sep 28
$188 total
Sep 27 - Sep 28
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 and ...
Holiday Inn Chicago – Midway Airport S by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$160 nightly
The price is $191 total per night from Sep 27 to Sep 28
$191 total
Sep 27 - Sep 28
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! (10,342 reviews)
"Security here is very odd Beatrice Ruiz got into a very verbal argument with me and threatened to have my car towed while I was brining my bags down to the front entrance would not recommend staying here on that note hotel had a very odd smell to it"

Reviewed on Sep 10, 2026

Congress Plaza Hotel
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$294 nightly
The price is $349 total per night from Sep 11 to Sep 12
$349 total
Sep 11 - Sep 12
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,409 reviews)
"The room did have a noticeable adhesive-like odor, similar to what I'd seen mentioned in another review. While it wasn't severe enough to ruin my stay, it was a little distracting. Guests who are sensitive to smells may find it bothersome. Despite that, I'm still giving 5 stars because I believe ..."

Reviewed on Sep 9, 2026

Hyatt Regency McCormick Place 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.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$160 nightly
The price is $191 total per night from Sep 27 to Sep 28
$191 total
Sep 27 - Sep 28
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! (10,342 reviews)
"Security here is very odd Beatrice Ruiz got into a very verbal argument with me and threatened to have my car towed while I was brining my bags down to the front entrance would not recommend staying here on that note hotel had a very odd smell to it"

Reviewed on Sep 10, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$179 nightly
The price is $213 total per night from Sep 21 to Sep 22
$213 total
Sep 21 - Sep 22
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (891 reviews)
"Great spot!"

Reviewed on Sep 7, 2026

Get rates
Kasa Magnificent Mile 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.

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
$53 nightly
The price is $60 total per night from Oct 1 to Oct 2
$60 total
Oct 1 - Oct 2
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 ...
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
$100 nightly
The price is $110 total per night from Oct 4 to Oct 5
$110 total
Oct 4 - Oct 5
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 ...
7.6/10 Good! (1,756 reviews)
"The continental breakfast was very good and shuttle to O’hare was timely. When we arrived at 6pm, there was no parking available due to an event not associated with the hotel, our room was not ready, and the workout room was closed. We were upgraded to a suite with a very comfortable bed, but the ..."

Reviewed on Sep 10, 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
$101 nightly
The price is $116 total per night from Sep 30 to Oct 1
$116 total
Sep 30 - Oct 1
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 ...
7.8/10 Good! (3,186 reviews)
"The air conditioning was broken. The fridge/freezer in the lobby snack shop was broken, which we realized after paying $18 for a 10oz serving of melted ice cream. The water jug in the lobby had debris floating in it. One of the two elevators was broken. The ice machine on our floor was broken. The ..."

Reviewed on Sep 9, 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
$224 nightly
The price is $266 total per night from Sep 22 to Sep 23
$266 total
Sep 22 - Sep 23
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. ...
7.8/10 Good! (3,392 reviews)
"👍"

Reviewed on Sep 10, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$164 nightly
The price is $195 total per night from Sep 29 to Sep 30
$195 total
Sep 29 - Sep 30
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 ...
7.6/10 Good! (2,823 reviews)
"The room was terrible. Right as you walked it you were hit with a stench. It smelled like a sweaty men’s locker room. There was no tv remote in the room and the tv was just sitting on. Then as I am about to get into bed to sleep there were bugs in the sheets under the comforter. DISGUSTING. WILL ..."

Reviewed on Sep 10, 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
$53 nightly
The price is $60 total per night from Oct 1 to Oct 2
$60 total
Oct 1 - Oct 2
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 ...
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
$262 nightly
The price is $311 total per night from Sep 20 to Sep 21
$311 total
Sep 20 - Sep 21
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 ...
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
$306 nightly
The price is $364 total per night from Sep 11 to Sep 12
$364 total
Sep 11 - Sep 12
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 ...
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
$177 nightly
The price is $241 total per night from Sep 20 to Sep 21
$241 total
Sep 20 - Sep 21
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! (5,986 reviews)
"The hotel is close to everything. Rooms are big, beds are comfy. Breakfast is okay. They have happy hour which offers you two free drinks which is nice. However, during check in, although we’ve arrived at 9:30am, way too early for check-in, the front desk did not accommodate us at all. And on top ..."

Reviewed on Sep 10, 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.