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Find cheap Delta flights to Chicago from $59

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Cheap Delta Flight Deals to Chicago

 
Here are some of the best deals found on KAYAK recently from Delta to Chicago 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 Delta flight deals to Chicago

KAYAK's recommended round-trip Delta deals departing in the coming months to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
7:20 am - 9:18 amBOS-ORD
2h 58mnonstop
Delta Logo
6:59 pm - 10:45 pmORD-BOS
2h 46mnonstop
$117Delta
Find Deal
Tue, Jun 10 - Fri, Jun 13
Delta Logo
11:00 am - 12:48 pmJFK-ORD
2h 48mnonstop
Delta Logo
6:18 pm - 10:00 pmORD-JFK
2h 42mnonstop
$137Delta
Find Deal
Tue, May 13 - Tue, May 13
Delta Logo
7:15 am - 8:56 amLGA-ORD
2h 41mnonstop
Delta Logo
8:15 pm - 11:40 pmORD-LGA
2h 25mnonstop
$137Delta
Find Deal
Tue, May 20 - Wed, May 21
Delta Logo
8:20 pm - 10:14 pmBOS-ORD
2h 54mnonstop
Delta Logo
2:15 pm - 5:47 pmORD-BOS
2h 32mnonstop
$137Delta
Find Deal
Tue, May 27 - Fri, Jun 6
Delta Logo
5:10 pm - 7:14 pmBOS-ORD
3h 04mnonstop
Delta Logo
7:00 am - 10:25 amORD-BOS
2h 25mnonstop
$138Delta
Find Deal
Sun, May 25 - Sat, May 31
Delta Logo
11:00 am - 12:48 pmJFK-ORD
2h 48mnonstop
Delta Logo
7:00 am - 10:25 amORD-JFK
2h 25mnonstop
$157Delta
Find Deal
Tue, May 13 - Wed, May 14
Delta Logo
8:55 pm - 10:41 pmLGA-ORD
2h 46mnonstop
Delta Logo
6:00 am - 9:10 amORD-LGA
2h 10mnonstop
$157Delta
Find Deal
Wed, May 14 - Tue, May 20
Delta Logo
8:20 pm - 10:14 pmBOS-ORD
2h 54mnonstop
Delta Logo
7:00 am - 10:25 amORD-BOS
2h 25mnonstop
$157Delta
Find Deal
Wed, May 28 - Sun, Jun 1
Delta Logo
7:15 am - 9:09 amBOS-ORD
2h 54mnonstop
Delta Logo
2:20 pm - 5:59 pmORD-BOS
2h 39mnonstop
$158Delta
Find Deal
Sat, May 31 - Tue, Jun 10
Delta Logo
8:20 pm - 10:14 pmBOS-ORD
2h 54mnonstop
Delta Logo
2:15 pm - 5:47 pmORD-BOS
2h 32mnonstop
$159Delta
Find Deal
Tue, May 27 - Wed, Jun 4
Useful Info

Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$59
Average price round-trip$471
Good deal round-trip$197
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Boston to Chicago O'Hare Airport
(avg. price over the last 2 weeks)
or less

When to book flights with Delta to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with Delta

  • Is Delta cheaper than other airlines flying to Chicago?

    With an average return price of $334, Delta is cheaper than United Airlines when it comes to flights to Chicago. However, the cheapest airline flying to Chicago is Allegiant Air, with an average return price of $131.

  • Which other airlines fly to Chicago?

    Along with Delta, you can also fly to Chicago with United Airlines, United Airlines, Southwest, American Airlines, Frontier, Contour, Denver Air Connection, Frontier, Southern / Mokulele, Allegiant Air and Allegiant Air.

  • How much is a flight to Chicago with Delta?

    On average, Delta flights to Chicago cost $334 for a round-trip.

  • Which airport do Delta flights to Chicago fly into?

    Delta flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford.

  • Are there any other airlines in SkyTeam that fly to Chicago?

    Unfortunately, there are no other airlines in SkyTeam that fly to Chicago.

Top tips for your flights to Chicago with Delta

  • The cheapest flight to Chicago with Delta found on KAYAK in the last 2 weeks departed from Minneapolis and cost $97.

Delta customer reviews

8.0
Very goodBased on 7,934 verified guest reviews
7.9Comfort
8.2Boarding
7.9Entertainment
8.5Crew
7.3Food

Pros +
Cons -
  • We had a 2.5 hour delay because there was someone missing in the crew. (in 99 reviews)

Show reviews that mention
Traveler rating:
Sort by:
A
10.0 Wonderful
Great
A
10.0 Wonderful
Fine except the person next to me took up her seat had raised the arm divide so she spilled into my seat. because of her size. Fortunately no one was in the seat on my right so I could use part of it.
A
10.0 Wonderful
All was very good!
B
6.0 Okay
Our bag was lost so that made unnecessary chaos On our trip
F
8.0 Very good
Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.
A
10.0 Wonderful
Perfect
R
10.0 Wonderful
Crew was friendly Love the entertainment in the seat head rest.
A
6.0 Okay
Long before take off and late at Seattle.
A
8.0 Very good
Delta flight was on time, seats were comfortable, and crew was nice.
R
10.0 Wonderful
Crew was great. Helpful friendly.

Everything you need to know for your flight to Chicago

Other airlines flying to Chicago

Flights from the other most popular airlines that fly to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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