$142 Cheap flights to Ashland County

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Ashland

Ashland

Cheap flights to Ashland County from $142 One Way, $284 Round Trip

$284 return flights and $142 one-way flights to Ashland County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 8 - Sun, Jan 10
ORD
Chicago
IWD
Ironwood
$284 Roundtrip, found 19 hours ago
$284
Roundtrip
found 19 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Jan 8 from Chicago to Ironwood, returning Sun, Jan 10, priced at $284 found 19 hours ago
Wed, Nov 25 - Sun, Nov 29
ORD
Chicago
IWD
Ironwood
$294 Roundtrip, found 2 days ago
$294
Roundtrip
found 2 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Wed, Nov 25 from Chicago to Ironwood, returning Sun, Nov 29, priced at $294 found 2 days ago
Thu, Nov 12 - Mon, Nov 16
ORD
Chicago
IWD
Ironwood
$304 Roundtrip, found 3 days ago
$304
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Nov 12 from Chicago to Ironwood, returning Mon, Nov 16, priced at $304 found 3 days ago
Sun, Nov 15 - Thu, Nov 19
ORD
Chicago
IWD
Ironwood
$310 Roundtrip, found 19 hours ago
$310
Roundtrip
found 19 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Nov 15 from Chicago to Ironwood, returning Thu, Nov 19, priced at $310 found 19 hours ago
Thu, Nov 12 - Mon, Nov 16
ORD
Chicago
IWD
Ironwood
$311 Roundtrip, found 3 days ago
$311
Roundtrip
found 3 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Nov 12 from Chicago to Ironwood, returning Mon, Nov 16, priced at $311 found 3 days ago
Fri, Nov 6 - Sun, Nov 8
ORD
Chicago
IWD
Ironwood
$332 Roundtrip, found 1 day ago
$332
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Nov 6 from Chicago to Ironwood, returning Sun, Nov 8, priced at $332 found 1 day ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
ORDIronwoodNovember 6 to November 8$332
ORDIronwoodNovember 6 to November 8$332
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Ashland County Accommodation Deals

Cobblestone Inn & Suites - Ashland

Cobblestone Inn & Suites - Ashland

2.5 out of 5
818 Main Street W. Ashland WI
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $164 total per night from Nov 1 to Nov 2
$164 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (866 reviews)
"Super clean, well maintained and quiet"

Reviewed on Oct 30, 2026

Opens in a new windowCobblestone Inn & Suites - Ashland
Lakeside Motel

Lakeside Motel

1706 Lake Shore Dr W Ashland WI
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $78 total per night from Dec 1 to Dec 2
$78 total
Dec 1 - Dec 2
Total with taxes and fees
Stay at this motel in Ashland. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Maslowski Beach and Ashland Mural Walk are located ...
9.6/10 Exceptional! (98 reviews)
"Stopped here during a long road trip. Highly highly recommended. Front desk clerk was awesome and helpful, the room was spotless and in good repair. Plenty of K cups, snacks, bottled water provided free. Mini fridge and microwave."

Reviewed on Oct 30, 2026

Opens in a new windowLakeside Motel
Hotel Chequamegon, BW Signature Collection

Hotel Chequamegon, BW Signature Collection

3 out of 5
101 Lake Shore Dr W Ashland WI
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $154 total per night from Dec 1 to Dec 2
$154 total
Dec 1 - Dec 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
Opens in a new windowHotel Chequamegon, BW Signature Collection
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Super 8 by Wyndham Ashland

Super 8 by Wyndham Ashland

2 out of 5
1610 Lake Shore Dr W Ashland WI
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $151 total per night from Nov 6 to Nov 7
$151 total
Nov 6 - Nov 7
Total with taxes and fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,000 reviews)
"We were surprised at how much we enjoyed staying there. It wasn’t just a hotel room. It was a “home base” where we could decompress peacefully in a comfortable room from the adventures we had through the day! The staff were amazing. This will definitely be the place we stay when we come to Ashland! ..."

Reviewed on Oct 29, 2026

Opens in a new windowSuper 8 by Wyndham Ashland
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Ashland County

Start your search for cheap flights to Ashland County on Orbitz. Orbitz is where you will discover guaranteed low prices on Ashland County flights, as well as all of the following conveniences:

Travel Updates on Your Mobile Device

Orbitz offers cutting-edge mobile tools for your smartphone. Whether you own an iPhone or an Android phone, you can benefit from Orbitz’s flight status updates and even book your future Ashland County flights. You can also review and reserve hotel rooms for when your Ashland County flights land and see other special offers.

Low Prices Guaranteed on Flights to Ashland County

Orbitz offers large discounts on a wide range of Ashland County flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Ashland County while taking advantage of the lowest fares around.

Customer Care When You Need It

Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Ashland County to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.

Loyalty Program Participation Opportunities

Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Ashland County. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.

Frequently asked questions

What is the best airport to fly to in Ashland County?
There's one major entrance point for this area — Gogebic County Airport (IWD). Book your airfares for this popular gateway and experience all that Ashland County has to offer.
How much is a flight to Ashland County?
Fares for return flights started as low as $284 this week to Ashland County, and reached a peak of $332. Several lucky passengers departing Chicago (ORD) managed to secure one-way fares starting from just $142.
How to book the cheapest flight to Ashland County?
With some of the most incredible flight deals around, you'll always bag a bargain with Orbitz. The following hints and tips will help you score cheap flights to Ashland County — and leave you with cash to spare:

  • Depending on where you're taking off from, select the 'Nearby airports' function (located under the departure and arrival form fields). In some instances, alternative departure points offer more competitive fares.
  • If your travel plans aren't set in concrete, click on the 'Show flexible dates' option to check out the flight deals across different departure dates. You may find an even better fare.
  • Hit 'Show options' to refine your search results. You can pick your preferred seating class and airline here. Under 'Sort & Filter' to the left, you can even select whether you'd like to fly in the morning, afternoon or evening.
  • Lock in your airfare as soon as you've worked out your travel dates. While it does happen occasionally, airline tickets rarely get cheaper as your date of departure gets closer.
  • Combine your flights, hotels and car rentals into a money-saving package deal. Save your hard-earned dollars for things you're really excited about, like exploring every corner of Ashland County.
  • Flying during peak season can mean steep airfares. Try to avoid traveling over popular periods, such as Christmas, New Year's Eve and Easter.

What is the best time to book a flight to Ashland County?
On average, the cheapest time to purchase a plane ticket is January. This is followed by February and August. When looking for a cheap flight to Ashland County, it's always good to be ready to book. Cheap deals emerge in an instant and don't hang around!
What day of the week is the cheapest to book a flight to Ashland County?
Make a booking on a Tuesday, Wednesday or Saturday. Typically, these are the cheapest days of the week to purchase seats to Ashland County. The getaway of your dreams starts with a fantastic flight deal!
What is the cheapest day of the week to fly to Ashland County?
You can score cheap flights to Ashland County by taking to the skies on a Monday, according to Orbitz data from 2020. Tuesday is also more affordable, while Saturday has the most costly ticket prices. Whether you prefer to save a bundle or take off on whichever day is convenient, you'll always get a wonderful deal with Orbitz.
What is the cheapest month to fly to Ashland County?
According to Orbitz data, you should fly out in August. This is generally the best month to pick up cheap flights to Ashland County. It's worth noting that the most expensive time to jet off is in the month of June.
Which airlines allow free cancellation?
Things change, and we think your flight should be able to do the same. That's why Orbitz makes it a breeze to search for flights with no change fees and free cancellation. Simply enter your departure and arrival destinations and then choose "Filter by flexible change policies." How's that for fuss-free?
What do I need for the flight to Ashland County?
From onboard entertainment to travel necessities like noise-canceling headphones, there are a few things a regular flyer always carries with them. To ensure you're all set for your adventure, have a read through this useful list:

  • Check that you've packed your travel paperwork and some identification. For international trips, you'll require your passport. When purchasing your flights, always use the same name, gender and birth date as indicated on your government-issued ID.
  • A well-packed carry-on bag is just the ticket for flying in comfort. Given this journey to Ashland County is no short hop, take a few snacks and things to keep you happy. Something to read will help you pass the time.
  • Together, air conditioning and high altitudes can produce a cool environment. No matter what the season is in Ashland County, pack a sweater to keep nice and toasty on your plane trip.

How do I get cheap first-class/business deals to Ashland County?
If you think a business or first-class fare is beyond your reach, think again. Here are some tips to help you book a premium flight to Ashland County for less:

  • Being flexible isn't confined to yoga. Leave some room to move around your travel dates so you can snap up cheaper airfares when a sale pops up.
  • Find a budget carrier that has business-class seats. They usually come with more legroom and a glass of Champagne — and a more affordable price.
  • Take advantage of your airline's frequent flyer program and use points to upgrade your seat. You can also bid for an upgrade in an online auction if available.

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.