Cheap flights from SBA to MDW (Santa Barbara Municipal to Midway Intl.)

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Cheap Flights from SBA to MDW starting at $121 One Way, $320 Round Trip

Prices starting at $320 for return flights and $121 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, Apr 7 - Sat, Apr 11
SBA
Santa Barbara
MDW
Chicago
$320 Roundtrip, found 2 days ago
$320
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Apr 7 from Santa Barbara to Chicago, returning Sat, Apr 11, priced at $320 found 2 days ago
Thu, Apr 9 - Mon, Apr 13
SBA
Santa Barbara
MDW
Chicago
$339 Roundtrip, found 2 days ago
$339
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Apr 9 from Santa Barbara to Chicago, returning Mon, Apr 13, priced at $339 found 2 days ago
Tue, Apr 7 - Sat, Apr 11
SBA
Santa Barbara
MDW
Chicago
$342 Roundtrip, found 2 days ago
$342
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Apr 7 from Santa Barbara to Chicago, returning Sat, Apr 11, priced at $342 found 2 days ago
Mon, Jan 26 - Tue, Feb 3
SBA
Santa Barbara
MDW
Chicago
$343 Roundtrip, found 5 days ago
$343
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Jan 26 from Santa Barbara to Chicago, returning Tue, Feb 3, priced at $343 found 5 days ago
Tue, Apr 7 - Sat, Apr 11
SBA
Santa Barbara
MDW
Chicago
$347 Roundtrip, found 2 days ago
$347
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Apr 7 from Santa Barbara to Chicago, returning Sat, Apr 11, priced at $347 found 2 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

3.5 out of 5
105 N MAY STREET Chicago IL
$144 nightly
The price is $169 total per night from Jan 25 to Jan 26
$169 total
Jan 25 - Jan 26
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 ...
8.8/10 Excellent! (1,151 reviews)
Clean hotel. Beautiful bar and very friendly employees!

Reviewed on Jan 10, 2026

Hyatt House Chicago West Loop
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
$95 nightly
The price is $111 total per night from Feb 1 to Feb 2
$111 total
Feb 1 - Feb 2
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! (1,875 reviews)
It was a perfect location and great value for the price

Reviewed on Jan 12, 2026

Crowne Plaza Chicago West Loop by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$87 nightly
The price is $102 total per night from Jan 24 to Jan 25
$102 total
Jan 24 - Jan 25
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! (9,777 reviews)
Clean and convenient!

Reviewed on Jan 16, 2026

Congress Plaza Hotel
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
$87 nightly
The price is $102 total per night from Jan 24 to Jan 25
$102 total
Jan 24 - Jan 25
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! (9,777 reviews)
Clean and convenient!

Reviewed on Jan 16, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$155 nightly
The price is $182 total per night from Feb 1 to Feb 2
$182 total
Feb 1 - Feb 2
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (2,530 reviews)
Great staff, good location .

Reviewed on Jan 14, 2026

Hilton 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
$111 nightly
The price is $130 total per night from Jan 25 to Jan 26
$130 total
Jan 25 - Jan 26
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! (5,548 reviews)
.

Reviewed on Jan 16, 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.

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
$38 nightly
The price is $43 total per night from Jan 25 to Jan 26
$43 total
Jan 25 - Jan 26
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! (1,774 reviews)
Everyone has gone above and beyond to accommodate my stay.. when in the area I would stay here again.

Reviewed on Jan 15, 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
$91 nightly
The price is $101 total per night from Jan 20 to Jan 21
$101 total
Jan 20 - Jan 21
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! (1,255 reviews)
Everything was real good and the people amazing

Reviewed on Jan 11, 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
$69 nightly
The price is $79 total per night from Jan 20 to Jan 21
$79 total
Jan 20 - Jan 21
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! (2,804 reviews)
Good room and great staff.

Reviewed on Jan 15, 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
$63 nightly
The price is $75 total per night from Feb 9 to Feb 10
$75 total
Feb 9 - Feb 10
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! (2,699 reviews)
would definitely stay again, good price point

Reviewed on Jan 16, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$72 nightly
The price is $85 total per night from Feb 8 to Feb 9
$85 total
Feb 8 - Feb 9
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! (2,504 reviews)
Only thing I would change is add mini fridges to the rooms.

Reviewed on Jan 10, 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
$38 nightly
The price is $43 total per night from Jan 25 to Jan 26
$43 total
Jan 25 - Jan 26
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! (1,774 reviews)
Everyone has gone above and beyond to accommodate my stay.. when in the area I would stay here again.

Reviewed on Jan 15, 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
$132 nightly
The price is $155 total per night from Jan 25 to Jan 26
$155 total
Jan 25 - Jan 26
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! (2,793 reviews)
Yes

Reviewed on Jan 13, 2026

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
$168 nightly
The price is $192 total per night from Jan 25 to Jan 26
$192 total
Jan 25 - Jan 26
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! (2,254 reviews)
.

Reviewed on Jan 18, 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
$111 nightly
The price is $130 total per night from Jan 25 to Jan 26
$130 total
Jan 25 - Jan 26
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! (5,548 reviews)
.

Reviewed on Jan 16, 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.

SBA 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 Santa Barbara Municipal Airport (SBA) to Midway Airport?
As you can't fly nonstop from Santa Barbara Municipal Airport (SBA) to Chicago Airport at this point in time, a flight with just one stopover is your best option. Southwest Airlines, Delta Air Lines and United Airlines are reputable airlines that operate on this route.
What is the shortest flight from SBA to Chicago Airport?
The fastest you can fly from Santa Barbara Airport to Chicago Airport is 5 hours and 19 minutes. Slip a few things into your carry-on to keep you entertained, like a fascinating read or a crossword puzzle.
How many hours flight from SBA to Chicago Airport?
It takes an average of 5 hours and 23 minutes to fly from SBA to MDW. Breeze through this medium-haul flight by watching some films and reading magazines. Alternatively, use the time to catch up on some sleep.
What airlines have the most flights from Santa Barbara Airport to Chicago Airport?
You'll need to make one or more stopovers if you're flying from SBA to MDW. Unfortunately, there aren't any airlines that have nonstop flights on 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.