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

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Cheap Flights from SAN to MDW starting at $79 One Way, $160 Round Trip

Prices starting at $160 for return flights and $79 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, Jan 21 - Tue, Jan 27
SAN
San Diego
MDW
Chicago
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Jan 21 from San Diego to Chicago, returning Tue, Jan 27, priced at $160 found 4 days ago
Wed, Jan 28 - Thu, Feb 5
SAN
San Diego
MDW
Chicago
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Jan 28 from San Diego to Chicago, returning Thu, Feb 5, priced at $167 found 2 days ago
Sat, Jan 17 - Tue, Jan 20
SAN
San Diego
MDW
Chicago
$170 Roundtrip, found 4 days ago
$170
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from San Diego to Chicago, returning Tue, Jan 20, priced at $170 found 4 days ago
Wed, Jan 21 - Tue, Jan 27
SAN
San Diego
MDW
Chicago
$175 Roundtrip, found 4 days ago
$175
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Jan 21 from San Diego to Chicago, returning Tue, Jan 27, priced at $175 found 4 days ago
Wed, Jan 28 - Thu, Feb 5
SAN
San Diego
MDW
Chicago
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Jan 28 from San Diego to Chicago, returning Thu, Feb 5, priced at $177 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
$88 nightly
The price is $104 total per night from Jan 11 to Jan 12
$104 total
Jan 11 - Jan 12, 2026
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 in ...
8.8/10 Excellent! (1,747 reviews)
Good experience would revisit for sure

Reviewed on Dec 9, 2025

Crowne Plaza Chicago West Loop by IHG
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
59 E. 11th Street Chicago IL
$79 nightly
The price is $93 total per night from Jan 5 to Jan 6
$93 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
8.6/10 Excellent! (2,123 reviews)
Nice new hotel, everything updated. Comfortable. Convenient location.

Reviewed on Dec 9, 2025

Homewood Suites by Hilton Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
$71 nightly
The price is $84 total per night from Jan 5 to Jan 6
$84 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,756 reviews)
clean room, close to food places, walkable & best part was no loud noise

Reviewed on Dec 12, 2025

Hilton Garden Inn Chicago Downtown South Loop
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$81 nightly
The price is $95 total per night from Jan 5 to Jan 6
$95 total
Jan 5 - Jan 6, 2026
Total with 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! (3,467 reviews)
I was allowed to check in early. Pleasant front desk staff. Nice room.

Reviewed on Dec 12, 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
$127 nightly
The price is $149 total per night from Dec 21 to Dec 22
$149 total
Dec 21 - Dec 22
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
9.2/10 Wonderful! (2,109 reviews)
Awesome stay in an amazing room - lobby and bar/restaurant area were excellent as well. Location was perfect for our show at the CIBC Theatre nearby.

Reviewed on Dec 10, 2025

Silversmith Hotel Chicago Downtown
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
$85 nightly
The price is $100 total per night from Dec 29 to Dec 30
$100 total
Dec 29 - Dec 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,966 reviews)
We loved the hotel, parking was a bit of a ways off.

Reviewed on Dec 10, 2025

Club Quarters Hotel Wacker at Michigan, 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
$43 nightly
The price is $48 total per night from Dec 28 to Dec 29
$48 total
Dec 28 - Dec 29
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! (1,719 reviews)
Parking was easy

Reviewed on Dec 8, 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
$91 nightly
The price is $101 total per night from Jan 11 to Jan 12
$101 total
Jan 11 - Jan 12, 2026
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 ...
7.2/10 Good! (1,204 reviews)
Close to airport and shuttle service

Reviewed on Dec 9, 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
$67 nightly
The price is $77 total per night from Dec 28 to Dec 29
$77 total
Dec 28 - Dec 29
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 ...
8/10 Very Good! (2,762 reviews)
I needed a hotel room when my flight was canceled late in the day and Comfort Suites was available. It turned out to be lucky for me. The staff was very friendly and helpful. The room was great for the price. I have no complaints at all.

Reviewed on Dec 8, 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
$65 nightly
The price is $77 total per night from Jan 4 to Jan 5
$77 total
Jan 4 - Jan 5, 2026
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! (2,638 reviews)
The front desk eas very easy to deal with and helpful

Reviewed on Dec 9, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$82 nightly
The price is $97 total per night from Dec 24 to Dec 25
$97 total
Dec 24 - Dec 25
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 ...
7.4/10 Good! (2,488 reviews)
Clean room, highly walkable location and friendly staff

Reviewed on Dec 12, 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
$43 nightly
The price is $48 total per night from Dec 28 to Dec 29
$48 total
Dec 28 - Dec 29
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! (1,719 reviews)
Parking was easy

Reviewed on Dec 8, 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
$102 nightly
The price is $120 total per night from Jan 11 to Jan 12
$120 total
Jan 11 - Jan 12, 2026
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 ...
8.2/10 Very Good! (2,741 reviews)
Clean room and friendly staff, overall good stay

Reviewed on Dec 12, 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
$136 nightly
The price is $155 total per night from Dec 21 to Dec 22
$155 total
Dec 21 - Dec 22
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 ...
8.4/10 Very Good! (2,123 reviews)
A beautiful hotel! The atmosphere is stunning. It was stunningly decorated for Christmas. Staff was very helpful and friendly, the rooms were clean and comfy; great pillows. Food at the hotel was delicious. The location is excellent. Right by the L, close to Millennium Park, near great restaurants. ...

Reviewed on Dec 12, 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
$96 nightly
The price is $113 total per night from Jan 6 to Jan 7
$113 total
Jan 6 - Jan 7, 2026
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 ...
8.4/10 Very Good! (5,385 reviews)
Spacious rooms , free drinks and great breakfast

Reviewed on Dec 14, 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.

SAN 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 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.