Find cheap flights from Illinois to Anguilla
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Round-trip
1 adult
Economy
Fri 3/3
Fri 3/10
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Good to know
Low season | May |
|---|---|
High season | November |
Cheapest flight | $693 |
Average price round-trip | $987 |
Good deal round-trip | $780 |
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Chicago O'Hare Intl to The Valley Wallblake Intl
(avg. price over the last 2 weeks)
or less
FAQs for booking flights from Illinois to Anguilla
Top airlines flying from Illinois to Anguilla
Scores according to KAYAK customer reviews7.9
DeltaOverall score based on 29326 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews
Pros: "Kosher snacks! Thank you. Screens and outlets at every seat. Safe, controlled Covid protocols including de-boarding. Excellent!"
Pros: "Kosher snacks! Thank you. Screens and outlets at every seat. Safe, controlled Covid protocols including de-boarding. Excellent!"
Pros: "Delta flight took extra precaution to keep all passengers safe before during and after the flight. They communicate effectively during the flight. I will be flying Delta again and again."
Cons: "The trip was great"
Cons: "We arrived around 39 minutes early and the whole process was very smooth"
Pros: "Super friendly and helpful with connections."
Cons: "The music on the plane was a bit much. Lol"
Pros: "Crew was friendly, seats really comfortable!"
Cons: "Headphones sold for $ 2. Headphones preferably free"
Pros: "Calm and safe, just like I like it."
Cons: "The carrots were hard and the bread was cold."
Pros: "Comfortable plane due to few passengers"
Cons: "7 hour delay after flight postponed."
Pros: "Got to my destination without any issues"
Cons: "Seats/seating area are too small, and I'm not a big person."
Pros: "All good."
Cons: "Price"
Cons: "No AC for an hour before takeoff - very uncomfortable. Audio for tv did not work."
Cons: "Flight was delayed a bit due to a couple passenger booking/misc issues. 1st class didn’t get gate bevfood service. Oven was busted so my meal wasn’t available. Entertainment console had all channels functional except — not really an issue I just really wanted to have ESPN playing in the background"
Pros: "Son got wings, so was happy."
Cons: "No entertainment."
Cons: "It was late"
Pros: "Good snack selection. Crew was personable."
Pros: "Crew was nice and welcoming"
Cons: "Well, if our plane had been leaving on time it would've been superb."
Cons: "Notify the delay quickly"
Pros: "Helpful"
Cons: "More print media to read on"
Pros: "Crew was great."
Cons: "Couldn’t hear/understand the pilot"
Pros: "Flight attendant in first class was amazing."
Pros: "Jeff was our flight attendant in first class. He is an excellent flight attendant. He has an amazing attitude and his manner made us feel as if we had been friends with him for years."
Cons: "Passengers who pay retail for first class on domestic flights should get access to the Delta lounges even without the AE card. Other airlines do this, and we have come to expect it."
Pros: "The boarding was fast and very well handled."
Cons: "My flight from Chicago was two hours late and that's why I missed the flight from Atlanta to Buenos Aires. No one helped and did not know that the flight was delayed and I had to find a place to sleep. I'm not satisfied with the experience and I have not yet arrived in Argentina because of the whole"
Cons: "It was delayed"
Pros: "N/A"
Cons: "Chinese Eastern did not try to help and solve my problem."
Pros: "It was a smooth boarding, flight and exit out of the plane."
Pros: "Snacks, cleanliness and crew"
Cons: "N/A"
Cons: "From the begging they changed the flights for something totally different. It was a 14 hour trip. Awful"
Cons: "Entertainment app from Go Go didn’t Work."
Pros: "It was a normal flight as well expected."
Pros: "I was with my friend"
Cons: "Delayed 12+ hours"
Pros: "We had a 2 1/2 delay due to mechanical issues but the crews, flight and ground, did a great job. Thanks."
Pros: "I was given a complimentary upgrade."
Cons: "It takes time and worries to find the air train and Aeroflot registration."
Pros: "My flight was great. Boarding was easy and the seats were comfortable."
Pros: "The service was amazing , the staff was honestly friendly and nice"
Pros: "Great service, nice agent friendly"
Pros: "Very friendly and professional gate agent and flight attendant"
Cons: "I was unable to fly at all due to a spelling error on my ticket. The airline refused to alter the ticket. Worst experience of my life, ruined my Christmas"
Pros: "Very nice flight and attentive staff. Enjoyed the view of NYC as we flew up the East River, then looped over Nassau County to approach LGA."
Cons: "The male flight attendant who handed out the complimentary drinks and snacks acted a bit strangely. I was very thirsty, and I asked him if I could keep the rest of the can of soda. He neither said yes nor no, but rather completely ignored what I said and just poured my drink and moved on. I was a mildly annoyed, but figured maybe it was policy and he was shy and didn't want to debate the matter. When he took care of the older couple behind us, however, things got really strange. He asked them whether they wanted pretzels or peanuts, but they misheard him and asked for a ginger ale. I happened to know that he did have ginger ale, since my wife had just gotten one, but rather than just pouring the old folks a drink, he repeated himself. "Peanuts or pretzels?" They misheard again and asked him whether he had a diet ginger ale. Again, rather than just pour them the drink, he repeated himself. "Peanuts or pretzels?" This went round and round a few more times -- like a poorly designed computer UI that refuses to accept anything except the correct input -- before the old couple finally figured out the disconnect and picked their snacks before their drinks. Very weird."
Pros: "Nothing"
Cons: "Cancelled my flight because I lost one of the arms"
Cons: "Layover"
Pros: "Short flight"
Cons: "Too cold Not friendly boarding agent"
Pros: "N/A"
Cons: "2.5 hour delay for no apparent reason at first (supposed mechanical issues with plane) and then waited on plane at gate for a missing pilot who never got picked up from his airport and got stuck in Chicago traffic trying to get to O'Hare. Eventually had to take pilot from another flight before leaving at 8:45 when flight was scheduled for 6:00am."
Cons: "Had a death in the family and no one would help me get back home"
Pros: "Seats were comfortable. Snacks!!! Nice flight crew."
Cons: "I liked everything."
Pros: "The Gogo Inflight wifi and entertainment did not work for even a minute. I choose flights based on their amenities and this one had offered full WIFI service which swayed me to choose to fly with Delta. I'm not sure who is to blame about this issue but I'm pretty frustrated that it was completely dysfunctional."
Pros: "The movie I watched was pleasant, although I had trouble hearing it because of the situation described below."
Cons: "There was a family seated behind us with several crying, loud children. We were miserable. Even my headphones with a Mozart sonata cranked up to loud did little to mask the noise. Probably not Dela'a fault, but the crew did nothing to mitigate the problem."
Cons: "Plane was sat broken at gate and needed part to be flown in. 150 minutes delayed. Not acceptable."
Pros: "No fee to get on an earlier flught"
Cons: "When I tried to rebook online this flight was not an option"
Pros: "Nothing"
Cons: "Individual TVs, perhaps"
Cons: "Late and then mechanical issues."
Pros: "Crew was great"
Cons: "Seat was uncomfortable. Flight was much too crowded"
Pros: "Flight was cancelled after multiple delays & I changed to United."
Cons: "Stop delaying & canceling flights, especially last minute"
Pros: "Really easy boarding and flight. Great in flight entertainment options."
Pros: "All was good"
Cons: "Nothing to complain about."
Pros: "Seat assignment process was great and considerate of my preferences."
Cons: "If AA could fix its luggage handling process that would be great. BOTH (!) of my bags have been lost on this flight. Both have been eventually located, recovered and delivered to me, but experience was not pleasant this time."
Pros: "Flight attendants were friendly and thoughtful."
Cons: "Seating is too tight. Hard to believe that in 2019, major airlines still have seats without any electrical or UBS outlets for charging devices."
Pros: "Crew was great."
Cons: "Plane was about 1000 years old and I don’t think I’ve sat in a more uncomfortable seat."
Cons: "Unable to connect to the new AA so-fi"
Pros: "Comfortable seats and snack / drinks service"
Cons: "Delayed flight departure and bumpy landing"
Cons: "I was apparently "flagged" by British Airways for extra security checks. As I understood it in London, I was randomly selected for this security check. This then apparently meant that I was to be flagged for all subsequent flights. This meant that in Chicago, after going through two other security checks that day (Zurich and London) and completing customs, I had to engage in a full Homeland security check. This involved removing protective covers from my laptop and phone that were hard to get off (not meant to be taken off regularly) and a full body search that I did not have to do in London. After many hours of traveling, this was very a frustrating experience."
Cons: "I will never, ever book with Kayak again"
Pros: "Flight crew was great. The plane was half full, so the attendants allowed us to move."
Cons: "Terrible landing in Charlotte. The plane was rattling and had an annoying whistle."
Cons: "British Airways/American Airlines lost/delayed luggage again! Then send an email in the middle of night with a link to schedule home delivery of the luggage that was valid for 4 hours only. It is clearly an attempt to cheat out of their responsibility of home delivery of the luggage that was delayed the second time. Poor, poor service by American Airlines."
Cons: "It was not clear that I needed a different 6 letter code to checkin using the AA website. I finally got frustrated and called AA only to find out the code was different. The codes should have been the same or you should have referenced it on the website when I tried to check in"
Cons: "Flight was delayed for more than 4 hours with little communication from staff as to why, gate was changed to a gate across the airport."
Pros: "The boarding was quick and easy as well as the crew was friendly and accommodating. Great end to a fun weekend away."
Pros: "Our plane was late getting to the gate. They kept us informed and turned it around pretty quickly. There were storms between Chicago and Rochester so we were rerouted. As a result the hour flight was an hour and a half. The pilot kept us informed and it was a very smooth flight. So even though I was over an hour late arriving I so appreciated the communications and the safer route. AA seems to be communicating more than other airlines and I appreciate that. Flying is absolutely no fun anymore so you take what you can get for the positives."
Cons: "WiFi wasn’t working so I couldn’t communicate my late arrival to family picking me up."
Cons: "On my first flight from SLC to ORD I asked 3 different American Airlines employees if I needed to pay for my carryon before I got on the plane. They all said no. I got on the plane, put my carryon under the seat in front of me and everything was great. I landed in Chicago, got to my gate, went to board and this very rude employee stopped me after I scanned my ticket and told me I couldn’t board with my bag. The EXACT bag I had boarded with in SLC. After harshly grabbing my bag and putting it in the carryon basket to check for size, she wouldn’t let me pass by her into the boarding bridge and told me I was going to have to pay. I tried explaining that I had asked I’m SLC if I needed to check it and they had all said no and that it fit under my seat. She said, “I don’t care what they said in SL, this is what I’m saying here.” And directed me to the front desk where I had to pay $50!! $50 for a carryon backpack that fit under my seat comfortably 20 minutes before!! Without saying a word (cause I didn’t want to yell at the poor girl behind the desk) I paid the $50 and proceeded to enter the bridge but before I passed through, the rude woman said, “have a nice flight ma’am” and scoffed!! An audible scoff. So I’m short, I hate American Airlines and I will do my BEST to not have to fly with them in the future."
Pros: "The fact that they re-booked without me having to contact customer service."
Cons: "The connecting flight was cancelled while boarding was in progress at the start of the journey."
Cons: "Flight was delayed by untold circumstances causing us to miss our connecting flight to Venice."
Pros: "On time departure and early arrival"
Cons: "Nothing"
Pros: "Nice crew Spacious plane"
Pros: "The crew was amazing, flight was very smooth, arrived early, plane clean, service was great."
Cons: "For being in first class, my seat did not recline so I couldn't sleep and audio for my entertainment center was not working"
Pros: "Good time for flight"
Cons: "Tight, hot inside plane, no refreshments"
Cons: "They left the lights on the whole flight"
Pros: "They alerted me to problems with our flight and we switched to an earlier flight. No problems with new flight. Good service."
Cons: "Great trip"
Pros: "Not turbulence"
Pros: "Was on time."
Cons: "Not eventful."
Pros: "crew was great, plane seemed newer and clean. individual screens worked better than others I've used in flights."
Cons: "newer touch screens were great except viewing angle couldn't be adjusted. standard food was horrible, esp for an international flight; not sure if specialty diets have better meals. kid movies were dubbed into many language options but Chinese was not one for ANY kid films. bathrooms with the same crappy mini sinks that you can't really wash your hands in, esp if someone pukes in it. they should all learn from Japan's ANA airliners with the motion sensor sinks with faucets raised up high enough for you to wash your hands without touching the gross basin."
Pros: "On time, good service."
Cons: "Luggage did not make the transfer on time (Chicago-Charlotte after Tokyo), although they had about 45 minutes to load it. Do not buy an international ticket with less than 1.5 hours transfer time. (It took 45 minutes to get through customs/immigration and retrieve luggage for transfer."
Cons: "Missed it."
Pros: "Nothing"
Cons: "An S80? Really? This plane was older than me! Horrible plane! The crew looked like they had been up since 4 am. Looked exhausted and unfriendly. I do want to clarify that this was an American Airlines operated plane, not etihad."
Cons: "The cramped space"
Cons: "All was excellent! Only the internet was not working good , payed for all flight access but most of the time the internet was not working. Anyway I contacted support team and they refunded me"
Cons: "The flight was delayed more times than I can count, we got a different reason each time. Weather I can understand, but telling us we are waiting on a specific crew to arrive and then announcing that crew is not for our flight was just terrible communication. No one seemed apologetic. The only thing they did was bring a snack cart over for us, and that got raided by children so many people didn't get anything. We had arranged transport from Orlando to Tampa for that evening, and our rides had to cancel because instead of 7pm we were now arriving at 130am. Your airline's mistakes put everyone at an inconvenience and we weren't offered assistance to fix it. My husband went to ask for help in arranging new transport home, but he couldn't even get to the front of the line. The customer service was terrible. We really enjoyed our first leg of the flight home with American Airlines, but after the second leg and all of the problems we had... we will not fly with American Airlines in the future."
Pros: "on time"
Cons: "very cold"
Cons: "This made the check in process extremely frustrating and confusing. Traveling with my elderly dad who had to squeeze between two large men for 7 hours because people who actually booked the airline got priority seating. We had to pay an extra $500 to upgrade to comfortable seats. Not pleased w Kayak."
Pros: "The crew was great and getting 2 meals was very nice."
Cons: "My headphone jack kept malfunctioning (loud popping noises in my earbuds) while watching the movie and all the reading lights came on and stayed on the majority of the flight so sleeping was difficult."
Pros: "An agent found me a window seat for the Chicago-Barcelona leg of the trip with extra leg room. That was amazing. Also, the lost luggage assistant for American Airlines was super helpful and nice. Also, the 787 (I think that was the Chicago-Barcelona craft) was a very enjoyable airplane. It was super smooth. It had high tech windows that adjusted the amount or type of light that could filter through the windows depending on the settings."
Cons: "When I arrived in Barcelona my Bag went missing. It showed up an two hours after my flight landed."
Pros: "I enjoyed the entertainment because I don't watch movies in the theater often. The movies I saw in-flight were recent films I've been wanting to see and made time pass fairly quickly."
Cons: "I'm not a giant, but there definitely was not enough leg room in the main cabin. I could not sit comfortably, especially in the middle seat."
Pros: "Good flight. Arrived on time"
Cons: "Jet bridge was broken and needed repair. Delayed departure."
Pros: "The crew were exceptionally friendly and helpful. They made the negatives about the flight much more bearably be their excellence service whether during boarding, in flight, or after landing."
Cons: "I booked the flight originally through british airways and expected your standard, modern plane for cross atlantic travel. Boarding to find myself on a 767 designed (and likely built) in the 80s was rather disappointing."
Pros: "Seats were really neither notably comfortable nor notably uncomfortable. I think they were slightly on the comfortable side."
Cons: "Would be nice to have more modern aircraft amenities, like power outlets for device charging, and display screens with at least some complimentary entertainment, or at least flight path tracking. Boarding counter lady was obnoxiously strict about not letting our carry-on bags to be carry-on. She made us test them in the size device and said they were too big, even though they could easy be pushed into the space, and regardless of the fact that we just flew on an American Airlines flight with them as carry-on and were only on a layover with them! Regarding the previous AA agent who let them be carry-on, she said "shame on them." Complete opposite of the positive experience we had with her counterpart in Phoenix. ಠ_ಠ"
Cons: "They cancelled the flight and put me to fly the next day"
Pros: "Everybody was nice my ride was comfortable and they treat me with respect"
Cons: "I like everything"
Book cheap flights from Illinois to Anguilla
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Flights to Anguilla
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