$104 Find Cheap Flights to Ashland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Ashland departing on 5/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$193
Denver Air Connection
So 6/21Mi 6/24
ORD - IWD • Non-stop
Cheapest one-way
$104
Denver Air Connection
Fr 5/8
ORD - IWD • Non-stop
Arrival airport
Ironwood (IWD)
You can't fly directly to Ashland. It is served by Ironwood (IWD), located 35.9 miles from Ashland.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights to Ashland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Ashland 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Ashland

So, Jun 21 - Mi, Jun 24
Denver Air Connection Logo
12:55 pm - 2:10 pm
ORD
-
IWD
1h 15mnonstop
Denver Air Connection Logo
2:40 pm - 3:55 pm
IWD
-
ORD
1h 15mnonstop
$193Denver Air Connection
Fr, Mai 8 - So, Mai 10
Denver Air Connection Logo
12:55 pm - 2:10 pm
ORD
-
IWD
1h 15mnonstop
Denver Air Connection Logo
2:40 pm - 3:55 pm
IWD
-
ORD
1h 15mnonstop
$208Denver Air Connection
Do, Apr 2 - Mo, Apr 6
Denver Air Connection Logo
10:30 am - 11:45 am
ORD
-
IWD
1h 15mnonstop
Denver Air Connection Logo
1:30 pm - 2:45 pm
IWD
-
ORD
1h 15mnonstop
$238Denver Air Connection
Fr, Mai 8 - So, Mai 10
Multiple Airlines Logo
12:55 pm - 2:10 pm
ORD
-
IWD
1h 15mnonstop
Multiple Airlines Logo
12:15 pm - 5:11 pm
IWD
-
ORD
4h 56m
1 stop
$310Multiple Airlines
So, Apr 5 - Do, Apr 9
Multiple Airlines Logo
10:30 am - 11:45 am
ORD
-
IWD
1h 15mnonstop
Multiple Airlines Logo
12:15 pm - 6:00 pm
IWD
-
ORD
5h 45m
1 stop
$343Multiple Airlines
Do, Apr 2 - Mo, Apr 6
Multiple Airlines Logo
6:25 pm - 1:00 pm
ORD
-
IWD
18h 35m
1 stop
Multiple Airlines Logo
1:30 pm - 2:45 pm
IWD
-
ORD
1h 15mnonstop
$354Multiple Airlines
Fr, Mai 8 - So, Mai 10
Multiple Airlines Logo
12:55 pm - 2:10 pm
ORD
-
IWD
1h 15mnonstop
Multiple Airlines Logo
12:15 pm - 10:46 am
IWD
-
ORD
22h 31m
3 stops
$357Multiple Airlines
Do, Apr 2 - Mo, Apr 6
Multiple Airlines Logo
10:30 am - 11:45 am
ORD
-
IWD
1h 15mnonstop
Multiple Airlines Logo
12:15 pm - 10:39 pm
IWD
-
ORD
34h 24m
3 stops
$386Multiple Airlines
Fr, Mai 8 - So, Mai 10
Multiple Airlines Logo
12:55 pm - 2:10 pm
ORD
-
IWD
1h 15mnonstop
Multiple Airlines Logo
12:15 pm - 1:44 pm
IWD
-
ORD
25h 29m
2 stops
$392Multiple Airlines
Fr, Apr 3 - Di, Apr 7
Multiple Airlines Logo
10:30 am - 11:45 am
ORD
-
IWD
1h 15mnonstop
Multiple Airlines Logo
12:15 pm - 10:39 pm
IWD
-
ORD
34h 24m
3 stops
$406Multiple Airlines
Useful Info

Good to know - Book Cheap Ashland Plane Tickets

Low seasonFebruary
Cheapest flight$104
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 Chicago to Ironwood

FAQs - booking Ashland flights

  • How long is the flight to Ashland?

    Flights from Chicago1h 15m

  • Which airlines fly to Ironwood?

    Many airlines fly to Ironwood, the most common ones being Delta, United Airlines, and Denver Air Connection. See the amount of flights per week for popular airlines flying to Ironwood.

  • How to fly to Ashland?

    You cannot fly directly to Ashland. KAYAK recommends you fly to Ironwood Gogebic County (IWD) (35.86 miles from Ashland). From there you can rent a car or get a taxi.

  • What airports are near Ashland?

    The closest airport is Duluth Intl (DLH) (64.36 mi). Another nearby airport is Rhinelander Oneida County (RHI) (95.23 mi). KAYAK recommends you fly to Ironwood Gogebic County.

  • How far is Ironwood Gogebic County Airport from central Ironwood?

    The city center of Ironwood is 5 miles from Ironwood Gogebic County Airport.

  • What is the name of Ironwood’s airport?

    Ironwood is served by Ironwood Gogebic County Airport, also commonly referred to as Gogebic County. The airport code is IWD.

  • How does KAYAK find such low prices on flights to Ashland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Ashland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Ashland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Ashland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Ashland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Ashland with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Ashland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Ashland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Ashland

  • There is no major airport in Ashland. It is instead served by Ironwood Gogebic County Airport.
  • Looking for a cheap flight? 25% of our users found flights on this route for $302 or less one-way.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Ashland flight deals.

Reviews of the top airline flying to Ashland

 
Need help choosing which airline to fly with from the United States to Ashland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
Denver Air ConnectionOverall score based on 24 reviews
8.2Food
7.6Entertainment
9.1Crew
8.6Comfort
8.2Boarding
Airline reviews

Missed connection flight because denver air connections plane was delayed a broke

2.0 MediocreAdin, Jan 2026
ORD - MKG
Read more Denver Air Connection reviews

Missed connection flight because denver air connections plane was delayed a broke

The crew handed out candy snacks, and water, which was great. However, the airport and airline are terrible at flying. Multiple delays on our departure flight and on return flight it was delayed so long that we missed the connection flight and had to drive home. Terrible service and did not get any compensation. All of their equipment was broken and they never tested it before the plane landed. We were stuck in Ironwood Michigan for five hours.

Denver air is great flight times and connections a little rough

Communication with delays. Failed to make a connection I ng flight in Chicago.

Excellent, from check Iin to arrival. I was apprehensive about flying a small plane between Ironwood and Chicago, but the flight and service was great. I noticed, after boarding , that my cell phone had little battery left. The flight attendant kindly lent me a charging device to keep me connected with my contact in Chicago upon landing. I will always remember that kindness.

Great snacks and friendly people for check in at Pierre SD!

The connecting flight came in 45 min late but everything else was great

Absolutely easy travels and no cost cutting by the airline.

Their snacks and hospitality was amazing. They offered full sized snacks. Im talking full sized water bottles, full sized snickers bars, gold fish, full sized canned sodas, what ever you wanted they took care of it for FREE. The crew was really nice and hospitable. I was honestly shocked

Everything you need to know for your flight to Ashland