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 3 days ago
$591
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Feb 24 from Evansville to Chicago, returning Fri, Apr 2, priced at $591 found 3 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 3 days ago
$781
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Feb 24 from Evansville to Chicago, returning Fri, Apr 2, priced at $781 found 3 days ago
Wed, Feb 24 - Fri, Apr 2
EVV
Evansville
MDW
Chicago
$801 Roundtrip, found 3 days ago
$801
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Feb 24 from Evansville to Chicago, returning Fri, Apr 2, priced at $801 found 3 days ago
Wed, Feb 24 - Fri, Apr 2
EVV
Evansville
MDW
Chicago
$881 Roundtrip, found 3 days ago
$881
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Feb 24 from Evansville to Chicago, returning Fri, Apr 2, priced at $881 found 3 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
$154 nightly
The price is $183 total per night from Sep 10 to Sep 11
$183 total
Sep 10 - Sep 11
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! (10,333 reviews)
"Excellent location, very clean and comfortable room."

Reviewed on Sep 9, 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
$284 nightly
The price is $337 total per night from Sep 10 to Sep 11
$337 total
Sep 10 - Sep 11
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 ...
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
$154 nightly
The price is $183 total per night from Sep 10 to Sep 11
$183 total
Sep 10 - Sep 11
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! (10,333 reviews)
"Excellent location, very clean and comfortable room."

Reviewed on Sep 9, 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 ...
8/10 Very Good! (2,191 reviews)
"The most disappointing thing was not having access to any bottled water at all: none in the room, no vending machine, front desk had none, bar and restaurant were both closed at the time we really needed it, after being out in nearly 100 degree heat looking for the beach. The beach is near, meaning ..."

Reviewed on Sep 9, 2026

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! (890 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 ...
7.8/10 Good! (1,997 reviews)
"I’m"

Reviewed on Sep 9, 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
$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! (1,753 reviews)
"Good for our overnight to catch an early flight."

Reviewed on Sep 9, 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 29 to Sep 30
$116 total
Sep 29 - Sep 30
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! (3,183 reviews)
"Go"

Reviewed on Sep 8, 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 23 to Sep 24
$266 total
Sep 23 - Sep 24
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. ...
Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$147 nightly
The price is $175 total per night from Sep 10 to Sep 11
$175 total
Sep 10 - Sep 11
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! (2,817 reviews)
"Staff was great"

Reviewed on Sep 9, 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 ...
7.8/10 Good! (1,997 reviews)
"I’m"

Reviewed on Sep 9, 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
$229 nightly
The price is $272 total per night from Sep 10 to Sep 11
$272 total
Sep 10 - Sep 11
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
$274 nightly
The price is $326 total per night from Sep 10 to Sep 11
$326 total
Sep 10 - Sep 11
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! (2,649 reviews)
"Perfect location, gorgeous lobby. Room was clean and large but needed some work (slightly peeling wallpaper, low water pressure). I'd stay there again, just don't expect the room condition to match the splendor of the common areas."

Reviewed on Sep 9, 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
$189 nightly
The price is $225 total per night from Sep 10 to Sep 11
$225 total
Sep 10 - Sep 11
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! (5,983 reviews)
"Good hotel value for money"

Reviewed on Sep 9, 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.