$100 Find Cheap Flights from Virginia to Illinois - Compare and Save

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Low season

January

Cheapest flight

$100
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Norfolk to Chicago Midway Airport

FAQs for booking flights from Virginia to Illinois

  • How does KAYAK find such low prices on flights from Virginia to Illinois?

    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 from Virginia to Illinois.

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

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

  • What is the Hacker Fare option on flights from Virginia to Illinois?

    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 from Virginia to Illinois 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 from Virginia to Illinois?

    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 from Virginia to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines fly most frequently to Illinois?

    Virginia and Illinois are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (139 flights per week), Air New Zealand (98 flights per week), and American Airlines (79 flights per week).

  • How many airports are there in Illinois?

    There are 12 airports in Illinois. The busiest airport is Chicago O'Hare Airport (ORD), with 91% of all flights arriving there.

  • Which is the cheapest airport to fly into in Illinois?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago Midway Airport (MDW), with an average flight price of $306.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Friday where round-trip tickets can be as cheap as $471. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $565 on average.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $454 on average. Morning departures are around 1% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $501.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Virginia found in the last 5 days was to Chicago O'Hare Intl Airport, at $233 round-trip. The most popular route is Charlottesville (CHO) to Chicago O'Hare Intl Airport (ORD) and the cheapest round-trip airline ticket found on this route in the last 5 days was $233.

  • What is the cheapest month to fly from Virginia to Illinois?

    The cheapest month for flights from Virginia to Illinois is June, when tickets cost $249 (return) on average. On the other hand, the most expensive months are November and September, when the average cost of round-trip tickets is $306 and $272 respectively.

  • How far in advance should I book a flight from Virginia to Illinois?

    To get a below average price on the flight from Virginia to Illinois, you should book around 4 weeks before departure, which saves you about 43% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

  • How many cities have direct flights to Illinois?

    From Virginia, there are direct flights to Illinois from 6 cities. The city with the most direct flights is Richmond, with 242 direct flights each week.

  • How many direct flights to Illinois are there each day?

    There are around 81 direct flights from within Virginia to Illinois every day. Most flights (67%) depart in the morning.

  • How many direct flights to Illinois are there each week?

    Each week there are around 561 direct flights from within Virginia to Illinois. The most common day for departures is Sunday, with 15% of flights taking off on this day.

  • How long is the flight to Illinois?

    An average nonstop flight from Virginia to Illinois takes 4h 21m, covering a distance of 635 miles. The shortest route is Washington, D.C. Reagan-National Airport (DCA) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 1h 57m.

  • How many long-haul flights are there to Illinois each week?

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Illinois. Instead, there are 561 short-haul flights (up to 3 hour flight duration), with the most arriving from Richmond.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (88% of total searches to Illinois). The next most popular destinations are St. Louis (9%) and Peoria (1%). Searches for flights to Moline (1%), to Evansville (0%) and to Bloomington (0%) are also popular.

Reviews of the top 5 airlines serving from Virginia to Illinois

 
Need help choosing which airline to fly with from Virginia to Illinois? 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.
8.0
SouthwestOverall score based on 4218 reviews
7.4Entertainment
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

2.0 MediocreKevin, Oct 2026
Read more Southwest reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Waited on tarmac to take off for approximately 15-25 minutes. When landing, the taxi to our gate took a similar amount of time. This happened on both of my United flights.

Fine except from Chicago to moline three different gate changes and flight times

When booking, the connection times seem fine. But in reality, my two connections were cut short by the first leg being delayed due to issues at the destination (too much traffic going into SFO, ORD) and it became extremely stressful.

Flight and crew were great. Need more legroom and do not allow seats to recline.

We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.

Just sat on the run way after we arrived early

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

They did the one thing that really matters - got to Chicago early.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

Both ways the people in the rear section of the plane were forced to check their carry on bags. I would understand this if the size and number of bags were not limited, but I do not understand why there is not room for one small overhead bag per person, even if the flight is full. I could watch the baggage handlers loading the extra luggage from my window and I’m pretty sure mine wouldn’t have survived undamaged, even though it is new and sturdy.

Entertainment, clean plane and funny pilot over the intercom was excellent… however, gate agent was rude and was probably a Spirit employee before they went bankrupt… there were 3 flight attendants - 2 of them didn’t want to be there the other one was kind and nice… I want you to recognize how you have to compete with Delta or South West airlines or even American Airlines which would choose over you at any given day from here on out. Please treat people respectfully. If you hate working in this industry - go and work somewhere else. The flight was very empty and it shouldn’t be hard to crack a smile once in a while. Very disappointing… I remember flying Jet Blue back in the day from Dulles IAD to LAX and you guys were super cool and fancy and made flying fun again - truly elevated the experience. Don’t become the next most hated airline… you can do better . I want you to succeed…

Free wifi was almost impossible to get, kept dropping the connection

Not good - we boarded and taxied for an hour before they told us there were technical issues with the plane. They told us we were going to need to deplane, parked back at the gate but then didn’t tell us we didn’t have to anymore. There was just a lot of uncertainties with poor communication.

3.5 hour delay because of “mundane” mx issue. Aircraft had to be towed 3 times.

Overall great experience, though my screen for entertainment was not working and I could see that others were.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

WiFi broken, very long wait for valet bags, and the typical long wait at O'Hare on a thursday to get clearance to take off and then again long taxi and wait for the gate.

The now boarding notification was not updated in the app until I was actually on the plan. This si a massive fail considering my flight was delayed several times. These types of failures add stress that could be avoided since I no longer feel comfortable leaving the boarding area to get food or visit a lounge. Had I used the notification from the app, I would have missed my flight. The secondly, the process of connecting to wifi on aa flights is clunky and could be streamlined better. the copy and past process feels like MVP, and you are well beyond that stage.

Both flights were late leaving due to repairs/switching gates. The crew and pilots, however, were professional and courteous. Most importantly, we arrived at our destination safely. The seats were comforable. That size should be standard for all economy class. American could improve its boarding process. I am not sure why you need 9 groups for a small regional plane.

It was close to its perfect the flake could be took off early, landed early, didn’t have to wait for my daughter stroller luggage came out quick, very efficient, very good flight

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.

No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.

Same the delay was not ideal and the credits to move flights was not sufficient

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Biggest issue was original flight canceled and booked to another flight 6 hours earlier and received no notification

Maximizing profits is one way to a healthy bottom line, the other is repeat business and referrals from satisfied customers. Frontier has clearly chosen the former. One of many examples: Family emergency required me to cut trip short. Headed to the airport to fly standby for the return trip I had already paid for (yes I understand prices vary with demand etc). Was told there is no standby and that I would need to pay for, despite what it's called by the company, what amounts to a new ticket. And surprise surprise, there turned out to be dozens of empty seats on that flight. To say nothing of the sleazy third and fourth party resellers, the flight/ticket insurance I elected and thought I had paid for that mysteriously wasn't there when I needed it before I left, and on and on with third world sleazy management decisions. The inflight coffee (that I had to pay for) was very good though.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

We were delayed three times ,and that destroyed my plans, and reservations

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

More options for your flight to Illinois

Complete your trip to Illinois with a hotel stay or car rental