Cheap flights from BOS to MDW (Logan Intl. to Midway Intl.)

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Cheap Flights from BOS to MDW starting at $59 One Way, $117 Round Trip

Prices starting at $117 for return flights and $59 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.

Sat, May 10 - Tue, May 13
BOS
Boston
MDW
Chicago
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, May 10 from Boston to Chicago, returning Tue, May 13, priced at $117 found 2 days ago
Mon, May 26 - Sat, May 31
BOS
Boston
MDW
Chicago
$119 Roundtrip, found 5 hours ago
$119
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Mon, May 26 from Boston to Chicago, returning Sat, May 31, priced at $119 found 5 hours ago
Sat, May 10 - Tue, May 13
BOS
Boston
MDW
Chicago
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, May 10 from Boston to Chicago, returning Tue, May 13, priced at $127 found 2 days ago
Mon, May 26 - Sat, May 31
BOS
Boston
MDW
Chicago
$129 Roundtrip, found 5 hours ago
$129
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Mon, May 26 from Boston to Chicago, returning Sat, May 31, priced at $129 found 5 hours ago
Thu, Jun 12 - Sun, Jun 15
BOS
Boston
MDW
Chicago
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Jun 12 from Boston to Chicago, returning Sun, Jun 15, priced at $157 found 2 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

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
The price is $143 per night from May 11 to May 12
$143
includes taxes & fees
$122 per night
May 11 - May 12
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,019 reviews)
"Nice location"

Reviewed on Apr 28, 2025

Crowne Plaza Chicago West Loop by IHG
Sonder South Wabash
Sonder South Wabash
3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
The price is $135 per night from May 26 to May 27
$135
includes taxes & fees
$115 per night
May 26 - May 27
Stay at this 3.5-star aparthotel in Chicago. Enjoy a fitness center, concierge services, and in-room washers/dryers. Popular attractions Soldier Field and Grant ...
8.8/10 Excellent! (482 reviews)
Enjoyable stay
"Decent studio apartment with a well stocked kitchen. Secure building, easy access with codes. Walkable to train and soldier field. Comfy bed, decent sized bathroom. Some noise in hall (doors, people talking) as expected but otherwise fairly quite building. We could hear the train but it didn’t disrupt ..."

Reviewed on Apr 24, 2025

Sonder South Wabash
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
506 West Harrison Street, Chicago, IL
The price is $149 per night from May 26 to May 27
$149
includes taxes & fees
$127 per night
May 26 - May 27
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8/10 Very Good! (1,006 reviews)
"Everything was just a small walk away"

Reviewed on Apr 26, 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.

Hotels In Chicago

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
The price is $189 per night from May 11 to May 12
$189
includes taxes & fees
$161 per night
May 11 - May 12
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,954 reviews)
"Very smooth check in, we had a great stay. Very helpful at the front not only at check in but with directions and help throughout the stay."

Reviewed on Apr 29, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $189 per night from May 27 to May 28
$189
includes taxes & fees
$161 per night
May 27 - May 28
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,733 reviews)
"Really nice hotel next to millennium park."

Reviewed on Apr 28, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is $183 per night from May 11 to May 12
$183
includes taxes & fees
$156 per night
May 11 - May 12
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 ...
8.8/10 Excellent! (2,163 reviews)
"Nice place to stay ! Walkable to the Michigan AVE where everything is. Quiet stay was lovely."

Reviewed on Apr 29, 2025

Hilton Chicago/Magnificent Mile Suites
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
The price is $62 per night from Apr 30 to May 1
$62
includes taxes & fees
$55 per night
Apr 30 - May 1
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! (1,429 reviews)
"It was ok. Staff were great. Provided what I needed but nothing great or impressive - beyond the staff, anyway. They were great."

Reviewed on Apr 26, 2025

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
The price is $102 per night from May 1 to May 2
$102
includes taxes & fees
$92 per night
May 1 - May 2
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
6.8/10 (1,002 reviews)
"I loved the breakfast! The only downside is that the temp was controlled with a energy saving thermostat that no matter how low I put the temp, it just wouldnt cool enough for my liking."

Reviewed on Apr 25, 2025

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
The price is $101 per night from May 13 to May 14
$101
includes taxes & fees
$88 per night
May 13 - May 14
Stay at this 3-star 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! (2,461 reviews)
"Very easy to navigate! And the bed was so comfortable! Clean room and there were stores conveniently within walking distance. Next door."

Reviewed on Apr 27, 2025

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
The price is $117 per night from May 26 to May 27
$117
includes taxes & fees
$100 per night
May 26 - May 27
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (1,749 reviews)
"My 2nd stay here. Great experience. Will be back for sure."

Reviewed on Apr 27, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
The price is $103 per night from Apr 30 to May 1
$103
includes taxes & fees
$87 per night
Apr 30 - May 1
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 ...
6.8/10 (2,108 reviews)
"Great location for walking"

Reviewed on Apr 29, 2025

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
The price is $62 per night from Apr 30 to May 1
$62
includes taxes & fees
$55 per night
Apr 30 - May 1
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! (1,429 reviews)
"It was ok. Staff were great. Provided what I needed but nothing great or impressive - beyond the staff, anyway. They were great."

Reviewed on Apr 26, 2025

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
The price is $210 per night from May 11 to May 12
$210
includes taxes & fees
$179 per night
May 11 - May 12
Stay at this 4-star 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! (2,660 reviews)
"We enjoyed our stay in the heart of Chicago. The Embassy Suites was clean, staff was very polite, helpful and professional. They serve a delicious daily breakfast. Happy hour daily and the Bartenders were great, polite and professional. Subway, sightseeing and entertainment is within walking ..."

Reviewed on Apr 27, 2025

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
The price is $204 per night from May 26 to May 27
$204
includes taxes & fees
$177 per night
May 26 - May 27
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,701 reviews)
"First of all i missed the fine print of additional $25 per stay charge. No water pressure in the shower. The hallways were a maze of confusion. And reminded us of the shining. The room could have used a microwave. With that being said, the staff was super friendly. The bed was comfortable. The rooms ..."

Reviewed on Apr 27, 2025

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
The price is $189 per night from May 11 to May 12
$189
includes taxes & fees
$161 per night
May 11 - May 12
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,954 reviews)
"Very smooth check in, we had a great stay. Very helpful at the front not only at check in but with directions and help throughout the stay."

Reviewed on Apr 29, 2025

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.

BOS to MDW Route Info

Origin Airport
Boston
Destination Airport
Chicago
Number Of Airlines Serving
1
Distance
857 mi
Shortest Flight Departure Time
2:05PM CDT
Shortest Flight Departure Date
May 6
BOS Address & GPS
Address:
One Harborside Drive
Boston MA, 02128-2909
United States
IATA Code:
BOS
Longitude:
-71.020176
Latitude:
42.36646
Time Zone:
America/New_York
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago

Frequently asked questions

Am I able to catch a flight from Boston, MA Airport (BOS-Logan Intl.) to Chicago, IL Airport (MDW-Midway Intl.) now?
The Covid-19 Travel Advisor can answer all your questions about travel restrictions and quarantine when taking a plane flight from Boston, MA Airport (BOS-Logan Intl.) to Chicago, IL Airport (MDW-Midway Intl.).
Are there non-stop flights from Boston, MA Airport (BOS-Logan Intl.) to Midway Airport?
We’re about to make your trip even better. Southwest Airlines flies direct from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW), so you’ll be embarking on your fantastic adventure in no time at all.
What is the shortest flight from BOS to Chicago Airport?
The shortest flight from Newton Highlands to West Lawn is 4 hours and 29 minutes. Order your favorite wine from the drink trolley, work on your travel itinerary or get to know your seat mate — you’ll have enough time on this medium-haul journey.
How many hours flight from Logan Intl. Airport to Chicago, IL Airport (MDW-Midway Intl.)?
On average, the flight from Logan Intl. Airport to Chicago Airport takes 4 hours and 34 minutes. If you’re eager to be as comfortable as you can, consider upgrading your seat using air miles or cash.
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago, IL Airport (MDW-Midway Intl.)?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago, IL Airport (MDW-Midway Intl.) have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Chicago, IL Airport (MDW-Midway Intl.) with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Chicago, IL Airport (MDW-Midway Intl.) without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What airlines have the most flights from Logan Intl. Airport to Chicago Airport?
Whether you choose a window or an aisle seat, you’ll fly to your destination smoothly and comfortably with Southwest Airlines. This reputable carrier operates 119 flights between BOS and MDW every month.

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.