ORD

Find cheap Southwest flights to Chicago O'Hare Intl Airport from $68

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Cheap Southwest Flight Deals to Chicago O'Hare Intl Airport

 
Here are some of the best deals found on KAYAK recently from Southwest to Chicago O'Hare Intl Airport that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip Southwest flight deals to Chicago O'Hare Intl Airport

KAYAK's recommended round-trip Southwest deals departing in the coming months to Chicago O'Hare Intl Airport.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
6:45 am - 3:00 pmBOS-ORD
9h 15m1 stop
Southwest Logo
4:00 pm - 11:55 pmORD-BOS
6h 55m1 stop
$136Southwest
Find Deal
Sat, Jun 7 - Wed, Jun 11
Southwest Logo
5:00 am - 12:45 pmBOS-ORD
8h 45m1 stop
Southwest Logo
4:00 pm - 11:55 pmORD-BOS
6h 55m1 stop
$142Southwest
Find Deal
Tue, Jul 1 - Tue, Jul 8
Southwest Logo
5:50 am - 1:05 pmBOS-ORD
8h 15m1 stop
Southwest Logo
1:50 pm - 10:45 pmORD-BOS
7h 55m1 stop
$148Southwest
Find Deal
Mon, Jun 16 - Thu, Jun 19
Southwest Logo
10:35 am - 11:50 amBWI-ORD
2h 15mnonstop
Southwest Logo
1:30 pm - 4:25 pmORD-BWI
1h 55mnonstop
$159Southwest
Find Deal
Sat, Jul 5 - Sat, Jul 26
Southwest Logo
10:35 am - 11:50 amBWI-ORD
2h 15mnonstop
Southwest Logo
1:50 pm - 4:50 pmORD-BWI
2h 00mnonstop
$168Southwest
Find Deal
Sat, Jul 5 - Thu, Jul 10
Southwest Logo
7:50 am - 12:45 pmBWI-ORD
5h 55m1 stop
Southwest Logo
1:50 pm - 4:50 pmORD-BWI
2h 00mnonstop
$169Southwest
Find Deal
Tue, Jul 1 - Thu, Jul 3
Southwest Logo
10:35 am - 11:50 amBWI-ORD
2h 15mnonstop
Southwest Logo
1:50 pm - 4:50 pmORD-BWI
2h 00mnonstop
$177Southwest
Find Deal
Mon, Jun 2 - Fri, Jun 6
Southwest Logo
10:35 am - 11:50 amBWI-ORD
2h 15mnonstop
Southwest Logo
6:00 am - 1:20 pmORD-BWI
6h 20m1 stop
$178Southwest
Find Deal
Mon, Jun 2 - Wed, Jun 4
Southwest Logo
10:45 am - 5:55 pmBWI-ORD
8h 10m1 stop
Southwest Logo
6:00 am - 1:20 pmORD-BWI
6h 20m1 stop
$179Southwest
Find Deal
Wed, May 28 - Wed, Jun 4
Southwest Logo
8:05 am - 4:25 pmBWI-ORD
9h 20m1 stop
Southwest Logo
4:00 pm - 9:25 pmORD-BWI
4h 25m1 stop
$184Southwest
Find Deal
Sat, Jun 21 - Tue, Jun 24
Useful Info

Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$68
Average price round-trip$263
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Boston to Chicago O'Hare Airport
(price for this month)

When to book flights with Southwest to Chicago O'Hare Intl Airport

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago O'Hare Intl Airport with Southwest

  • Which other airlines fly to Chicago O'Hare Intl Airport?

    Along with Southwest, you can also fly to Chicago O'Hare Intl Airport with United Airlines, United Airlines, American Airlines, Contour, Denver Air Connection and Southern / Mokulele.

  • How much is a flight to Chicago O'Hare Intl Airport with Southwest?

    On average, Southwest flights to Chicago O'Hare Intl Airport cost $162 one-way.

  • Which airport do Southwest flights to Chicago O'Hare Intl Airport fly into?

    You’ll fly into Chicago O'Hare Airport when flying to Chicago O'Hare Intl Airport with Southwest.

Top tips for your flights to Chicago O'Hare Intl Airport with Southwest

  • The cheapest flight to Chicago O'Hare Intl Airport with Southwest found on KAYAK in the last 2 weeks departed from Dallas Love Field Airport and cost $73.

Southwest customer reviews

8.0
Very goodBased on 4,294 verified guest reviews
8.0Comfort
8.2Boarding
7.6Entertainment
8.6Crew
7.1Food
Pros +
Cons -
Show reviews that mention
Traveler rating:
Sort by:
K
8.0 Very good
Start drink service earlier. We were rushed.
J
8.0 Very good
It is southwest seat was ok. Not the most comfortable seat
H
6.0 Okay
They were more than 2 hours late.
H
10.0 Wonderful
Good
J
8.0 Very good
I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight
J
6.0 Okay
The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.
A
10.0 Wonderful
Plz don't take away free bags and free seating
D
6.0 Okay
The seats were a bit cramped and worn, but otherwise okay.
D
6.0 Okay
The seats were a bit cramped, but otherwise okay.
A
8.0 Very good
It departed late
Read more about Southwest

Everything you need to know for your flight to Chicago O'Hare Intl Airport

Other airlines flying to Chicago O'Hare Intl Airport

Flight deals from the most popular airlines with KAYAK users flying the route
United Airlines flights to Chicago O'Hare Intl Airport
American Airlines flights to Chicago O'Hare Intl Airport

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