$269 Find Cheap Flights from Chicago Midway Airport to Aruba - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Aruba flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Chicago Midway Airport to Aruba right now?

The cheapest fare from Chicago Midway Airport to Aruba in the last week was $594 round-trip, to Oranjestad Reina Beatrix (AUA).

Which airport in Aruba is the cheapest to fly to from Chicago Midway Airport?

All flights from Chicago Midway Airport to Aruba arrive at Oranjestad Reina Beatrix (AUA). On average, round-trip fares are around $737.

What’s the cheapest day to fly from Chicago Midway Airport to Aruba?

Saturday tends to be the cheapest day to fly from Chicago Midway Airport to Aruba, while Friday is the most expensive. Fares run about 43% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Chicago Midway Airport to Aruba?

Data from the past 12 months shows it's cheapest to fly to Aruba during the evening, but the difference compared with the morning, the most expensive time to fly, is minimal, just 1%.

Key details for Chicago Midway Airport to Aruba flights

Low season

February

Cheapest flight

$264
Beat the crowds with an average 94% drop in travelers.
The most popular month to fly with an average 60% increase in travelers.
One-way flight from Chicago Midway Airport to Oranjestad

Your Chicago Midway Airport to Aruba flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago Midway Airport to Aruba?

    Yes. Fares from Chicago Midway Airport to Aruba are low right now. As a rule of thumb, a round-trip under $681 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Chicago Midway Airport to Aruba?

    Over the past 12 months, round-trip fares from Chicago Midway Airport to Aruba have ranged from $681 to $921.

  • What are the main airports serving Aruba?

    Flights to Aruba all arrive at Oranjestad Reina Beatrix (AUA).

  • What airlines fly nonstop from Chicago Midway Airport to Aruba?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Chicago Midway Airport to Aruba. One-stop options include Delta and Southwest.

  • Which cabin classes are available on flights from Chicago Midway Airport to Aruba?

    On flights from Chicago Midway Airport to Aruba you can only book Economy Class.

Your guide to booking Chicago Midway Airport to Aruba flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for March when flights are typically cheapest and avoid November when prices are at their highest.
  • Flying on Saturday is usually the cheapest. Flights on Friday cost about 43% more on average, so being flexible with your travel dates could help you save.
  • Start your trip in Oranjestad, which is the most popular destination in Aruba. From there, it's easy to continue on to other popular destinations such as Noord, Sint Nicolaas and Santa Cruz.

Reviews of the top airline flying from Midway to Aruba

 
Need help choosing which airline to fly with from Midway to Aruba? 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 4212 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

More options for your flight from Midway to Aruba

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