Cheap flights from SAN to MDW (San Diego Intl. to Midway Intl.)

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Cheap Flights from SAN to MDW starting at $75 One Way, $154 Round Trip

Prices starting at $154 for return flights and $75 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, Aug 5 - Sat, Aug 9
SAN
San Diego
MDW
Chicago
$154 Roundtrip, found 5 days ago
$154
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Aug 5 from San Diego to Chicago, returning Sat, Aug 9, priced at $154 found 5 days ago
Wed, Aug 6 - Sat, Aug 9
SAN
San Diego
MDW
Chicago
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Aug 6 from San Diego to Chicago, returning Sat, Aug 9, priced at $157 found 5 days ago
Tue, Sep 30 - Tue, Oct 7
SAN
San Diego
MDW
Chicago
$161 Roundtrip, found 15 hours ago
$161
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Tue, Sep 30 from San Diego to Chicago, returning Tue, Oct 7, priced at $161 found 15 hours ago
Tue, Sep 23 - Sun, Sep 28
SAN
San Diego
MDW
Chicago
$199 Roundtrip, found 3 days ago
$199
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Sep 23 from San Diego to Chicago, returning Sun, Sep 28, priced at $199 found 3 days ago
Tue, Sep 30 - Tue, Oct 7
SAN
San Diego
MDW
Chicago
$209 Roundtrip, found 15 hours ago
$209
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Tue, Sep 30 from San Diego to Chicago, returning Tue, Oct 7, priced at $209 found 15 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Cozy and Modern Stay in the Heart of C
Cozy and Modern Stay in the Heart of C
3 out of 5
1407 w 15th St Chicago, Chicago, IL
Stay at this 3-star motel in Chicago. Enjoy free WiFi, in-room washers/dryers, and air conditioning. Popular attractions United Center and Grant Park are located ...
5.2/10 (14 reviews)
"It was good to stay there. Had good traveling. Thank you for taking care of staying safety!"

Reviewed on Jun 5, 2025

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Cozy and Modern Stay in the Heart of C
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
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! (1,116 reviews)
"Very convenient."

Reviewed on Jun 11, 2025

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Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
506 West Harrison Street, Chicago, IL
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)
"Great!"

Reviewed on Jun 11, 2025

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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
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! (4,196 reviews)
"Great location and breakfast n happy hour are a plus"

Reviewed on Jun 11, 2025

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Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
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! (1,861 reviews)
"It’s a beautiful hotel in a great spot, just a little dated."

Reviewed on Jun 10, 2025

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InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
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! (2,289 reviews)
"My check-in was not so pleasant. I did arrive early and knew I would need to wait which was no problem. I was told I could check my bags at the bell desk but no one was there after standing for a bit finally some out it the 3 people at the front desk asked if I needed help. When I checked in about ..."

Reviewed on Jun 11, 2025

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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
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! (1,487 reviews)
"Room was clean and allowed early check in"

Reviewed on Jun 11, 2025

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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
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 (1,007 reviews)
"I was waiting for a long time for someone to check me in. Shuttle driver help me to contact dome one. He has a great customer service"

Reviewed on Jun 9, 2025

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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
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! (2,512 reviews)
"Love it"

Reviewed on Jun 10, 2025

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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
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! (1,920 reviews)
"Nice place, good staff, fun place."

Reviewed on Jun 10, 2025

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Freehand Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
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 ...
7/10 Good! (2,202 reviews)
"Okay"

Reviewed on Jun 13, 2025

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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
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! (1,487 reviews)
"Room was clean and allowed early check in"

Reviewed on Jun 11, 2025

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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
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! (2,670 reviews)
"I loved the location"

Reviewed on Jun 8, 2025

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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
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! (1,741 reviews)
"We loved the interior decor and seating."

Reviewed on Jun 11, 2025

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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
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! (4,196 reviews)
"Great location and breakfast n happy hour are a plus"

Reviewed on Jun 11, 2025

Get rates
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.

SAN to MDW Route Info

Origin Airport
San Diego
Destination Airport
Chicago
Number Of Airlines Serving
1
Distance
1725 mi
Shortest Flight Departure Time
5:45PM PDT
Shortest Flight Departure Date
Jun 20

Frequently asked questions

Are there non-stop flights from San Diego Airport to MDW?
Listen up. We’re about to make your trip even better. Southwest Airlines flies directly from San Diego Intl. Airport (SAN) to Chicago Airport, so you’ll be starting your next big adventure in no time at all.
What is the shortest flight from San Diego Airport to Chicago Airport?
Treat yourself to an in-flight vino and get comfy in your seat with a fascinating movie or book. With the flight from San Diego to Chicago taking 5 hours and 8 minutes, you’ll have enough time to relax and enjoy the experience.
How many hours flight from San Diego Intl. Airport (SAN) to Midway Airport?
Usually, the flight from San Diego Intl. Airport (SAN) to Midway Airport takes 5 hours and 12 minutes. If you’re eager to be as comfy as possible, try upgrading your seat using air miles or cash.
What airlines have the most flights from SAN to Chicago Airport?
If you want a worry-free trip, consider reserving your ticket with Southwest Airlines. This air carrier has 119 flights each month between San Diego and Chicago and is one of the leading airlines servicing this route.

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.