Cheap flights from SAN to MDW (San Diego Intl. to Midway Intl.)
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Cheap Flights from SAN to MDW starting at $70 One Way, $139 Round Trip
Prices starting at $139 for return flights and $70 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.
SAN
San Diego
MDW
Chicago
$139 Roundtrip, found 1 hour ago
$139
Roundtrip
found 1 hour ago
SAN
San Diego
MDW
Chicago
$141 Roundtrip, found 10 hours ago
$141
Roundtrip
found 10 hours ago
SAN
San Diego
MDW
Chicago
$149 Roundtrip, found 6 days ago
$149
Roundtrip
found 6 days ago
SAN
San Diego
MDW
Chicago
$158 Roundtrip, found 1 hour ago
$158
Roundtrip
found 1 hour ago
SAN
San Diego
MDW
Chicago
$160 Roundtrip, found 10 hours ago
$160
Roundtrip
found 10 hours ago
Hotel Ideas near Midway Intl.
Airport Hotels near Midway Intl.
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
$146 nightly
The price is $171 total per night from Aug 24 to Aug 25
$171 total
Aug 24 - Aug 25
Total includes taxes and fees
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! (1,324 reviews)
"It is renovated, it is very clean, the breakfast was delicious"
Reviewed on Jul 30, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
$170 nightly
The price is $200 total per night from Aug 18 to Aug 19
$200 total
Aug 18 - Aug 19
Total includes taxes and fees
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! (9,040 reviews)
"The best"
Reviewed on Jul 30, 2025
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street, Chicago, IL
$171 nightly
The price is $201 total per night from Aug 24 to Aug 25
$201 total
Aug 24 - Aug 25
Total includes taxes and fees
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 ...
8.2/10 Very Good! (1,003 reviews)
Convenient location
"Very close to Clinton blue line if you plan on taking public transportation. Quiet hotel with roof top pool. The staff were friendly and helpful. Our only complaint was how tight the bathroom was. For a family you couldn’t fit more than one in the bathroom to get ready at once."
Reviewed on Jul 29, 2025
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
520 South Michigan Avenue, Chicago, IL
$170 nightly
The price is $200 total per night from Aug 18 to Aug 19
$200 total
Aug 18 - Aug 19
Total includes taxes and fees
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! (9,040 reviews)
"The best"
Reviewed on Jul 30, 2025
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
$261 nightly
The price is $301 total per night from Aug 17 to Aug 18
$301 total
Aug 17 - Aug 18
Total includes taxes and fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,132 reviews)
"We came for a wedding and had a blast! This hotel is beautiful and we love it!"
Reviewed on Jul 31, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
$144 nightly
The price is $169 total per night from Aug 17 to Aug 18
$169 total
Aug 17 - Aug 18
Total includes 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 ...
8.8/10 Excellent! (2,564 reviews)
"Nice size room, walking distance to everything , great staff"
Reviewed on Jul 29, 2025
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
2881 Touhy Ave, Elk Grove Village, IL
$60 nightly
The price is $68 total per night from Aug 20 to Aug 21
$68 total
Aug 20 - Aug 21
Total includes 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! (1,576 reviews)
Great spot with free stays for pets
"If you need a clean place to stay with free parking that allows free pets this is the spot for you. It's a no frills and safe spot to lay your head down. The front desk is excellent and friendly and it's conveniently located near O'Hare. My cats enjoyed it."
Reviewed on Jul 31, 2025
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
777 E Grand Avenue, Bensenville, IL
$115 nightly
The price is $127 total per night from Aug 17 to Aug 18
$127 total
Aug 17 - Aug 18
Total includes taxes and fees
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 ...
7/10 Good! (1,037 reviews)
"Great rate. Room was comfortable and clean and spacious. Walking distance to shops nearby. Shuttle to Airport made it convenient. Staff was nice. Had a small store in hotel with snacks. Pool was open which was nice. Do recommend a room in back of hotel to avoid traffic noice from the street"
Reviewed on Jul 29, 2025
Comfort Suites Chicago O'Hare Airport
4200 North River Road, Schiller Park, IL
$94 nightly
The price is $107 total per night from Aug 18 to Aug 19
$107 total
Aug 18 - Aug 19
Total includes taxes and fees
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! (2,579 reviews)
"Room smells smoky"
Reviewed on Jul 28, 2025
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
19 East Ohio Street, Chicago, IL
$145 nightly
The price is $170 total per night from Aug 24 to Aug 25
$170 total
Aug 24 - Aug 25
Total includes taxes and fees
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! (2,131 reviews)
"Good"
Reviewed on Jul 28, 2025
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
$107 nightly
The price is $126 total per night from Aug 25 to Aug 26
$126 total
Aug 25 - Aug 26
Total includes 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 ...
7.2/10 Good! (2,249 reviews)
"The building is old but clean. The bed was comfortable."
Reviewed on Jul 29, 2025
Motel 6 Elk Grove Village, IL - O'Hare
2881 Touhy Ave, Elk Grove Village, IL
$60 nightly
The price is $68 total per night from Aug 20 to Aug 21
$68 total
Aug 20 - Aug 21
Total includes 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! (1,576 reviews)
Great spot with free stays for pets
"If you need a clean place to stay with free parking that allows free pets this is the spot for you. It's a no frills and safe spot to lay your head down. The front desk is excellent and friendly and it's conveniently located near O'Hare. My cats enjoyed it."
Reviewed on Jul 31, 2025
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
511 North Columbus Drive, Chicago, IL
$196 nightly
The price is $230 total per night from Aug 24 to Aug 25
$230 total
Aug 24 - Aug 25
Total includes taxes and fees
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! (2,746 reviews)
"Good hotel, close to many attractions"
Reviewed on Jul 27, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
$198 nightly
The price is $229 total per night from Aug 21 to Aug 22
$229 total
Aug 21 - Aug 22
Total includes taxes and fees
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! (1,819 reviews)
"Nice place to stay"
Reviewed on Jul 29, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
$174 nightly
The price is $204 total per night from Aug 24 to Aug 25
$204 total
Aug 24 - Aug 25
Total includes taxes and fees
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. ...
8.4/10 Very Good! (4,566 reviews)
"Parking was outrageous and be prepared for."
Reviewed on Jul 29, 2025
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.
SAN to MDW Route Info
Origin Airport | San Diego |
|---|---|
Destination Airport | Chicago |
Number Of Airlines Serving | 1 |
Distance | 1725 mi |
Shortest Flight Departure Time | 1:40PM PDT |
Shortest Flight Departure Date | Aug 7 |
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SAN Address & GPS
Address:
Airport Drive
San Diego CA, 92101
United States
IATA Code:
SAN
Longitude:
-117.197312
Latitude:
32.731938
Time Zone:
America/Los_Angeles
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
Other Flights from San Diego Intl. Airport (SAN)
Other Flights to Midway Intl. Airport (MDW)
- Montgomery Field Airport (MYF)
- Gillespie Field Airport (SEE)
- McClellan-Palomar Airport (CLD)
- French Valley Airport (RBK)
- John Wayne Airport (SNA)
- Catalina Airport (AVX)
- Palm Springs Intl. Airport (PSP)
- Jacqueline Cochran Regional Airport (TRM)
- Bermuda Dunes Airport (UDD)
- Fullerton Municipal Airport (FUL)
Frequently asked questions
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.