Cheap flights from Chicago Midway to Liberia

Compare Chicago Midway to Liberia flight deals

Find the cheapest month or even day of the year to fly to Liberia

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Flight deals from Chicago Midway to Liberia

Looking for a cheap last-minute deal or the best round-trip flight from Chicago Midway Airport to Liberia Airport? If you want to travel next month, round-trip fares start from $506. Find the lowest prices on one-way and round-trip tickets right here.

Liberia.$494 per passenger.Departing Sun, Nov 15, returning Fri, Nov 20.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Sun, Nov 15, arriving in Liberia.Inbound indirect flight with Southwest Airlines, departing from Liberia on Fri, Nov 20, arriving in Chicago Midway.Price includes taxes and charges.From $494, select.

Liberia.$502 per passenger.Departing Fri, Oct 16, returning Sat, Oct 24.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Fri, Oct 16, arriving in Liberia.Inbound indirect flight with Southwest Airlines, departing from Liberia on Sat, Oct 24, arriving in Chicago Midway.Price includes taxes and charges.From $502, select.

Liberia.$505 per passenger.Departing Sun, Dec 6, returning Wed, Dec 9.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Sun, Dec 6, arriving in Liberia.Inbound indirect flight with Southwest Airlines, departing from Liberia on Wed, Dec 9, arriving in Chicago Midway.Price includes taxes and charges.From $505, select.

Liberia.$506 per passenger.Departing Sun, Sep 20, returning Sat, Sep 26.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Sun, Sep 20, arriving in Liberia.Inbound indirect flight with Southwest Airlines, departing from Liberia on Sat, Sep 26, arriving in Chicago Midway.Price includes taxes and charges.From $506, select.

Liberia.$633 per passenger.Departing Wed, Aug 26, returning Wed, Sep 2.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago Midway on Wed, Aug 26, arriving in Liberia.Inbound indirect flight with Delta, departing from Liberia on Wed, Sep 2, arriving in Chicago Midway.Price includes taxes and charges.From $633, select.

Liberia.$638 per passenger.Departing Sat, Nov 28, returning Sat, Dec 5.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Sat, Nov 28, arriving in Liberia.Inbound indirect flight with Southwest Airlines, departing from Liberia on Sat, Dec 5, arriving in Chicago Midway.Price includes taxes and charges.From $638, select.

Liberia.$643 per passenger.Departing Tue, Jan 26, returning Tue, Feb 2.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Tue, Jan 26, arriving in Liberia.Inbound indirect flight with Southwest Airlines, departing from Liberia on Tue, Feb 2, arriving in Chicago Midway.Price includes taxes and charges.From $643, select.

Liberia.$651 per passenger.Departing Wed, Jan 13, returning Wed, Jan 20.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Wed, Jan 13, arriving in Liberia.Inbound indirect flight with Southwest Airlines, departing from Liberia on Wed, Jan 20, arriving in Chicago Midway.Price includes taxes and charges.From $651, select.

Liberia.$655 per passenger.Departing Sun, Dec 13, returning Wed, Jan 13.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Sun, Dec 13, arriving in Liberia.Inbound indirect flight with Southwest Airlines, departing from Liberia on Wed, Jan 13, arriving in Chicago Midway.Price includes taxes and charges.From $655, select.

Liberia.$724 per passenger.Departing Fri, Feb 19, returning Thu, Feb 25.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Fri, Feb 19, arriving in Liberia.Inbound indirect flight with Southwest Airlines, departing from Liberia on Thu, Feb 25, arriving in Chicago Midway.Price includes taxes and charges.From $724, select.

Liberia.$837 per passenger.Departing Wed, Mar 31, returning Tue, Apr 6.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago Midway on Wed, Mar 31, arriving in Liberia.Inbound indirect flight with Delta, departing from Liberia on Tue, Apr 6, arriving in Chicago Midway.Price includes taxes and charges.From $837, select.

Liberia.$858 per passenger.Departing Mon, Aug 24, returning Sun, Aug 30.Round-trip flight with Porter Airlines and WestJet.Outbound indirect flight with Porter Airlines, departing from Chicago Midway on Mon, Aug 24, arriving in Liberia.Inbound indirect flight with WestJet, departing from Liberia on Sun, Aug 30, arriving in Chicago Midway.Price includes taxes and charges.From $858, select.

Liberia.$869 per passenger.Departing Sat, Feb 27, returning Sat, Mar 6.Round-trip flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departing from Chicago Midway on Sat, Feb 27, arriving in Liberia.Inbound indirect flight with Southwest Airlines, departing from Liberia on Sat, Mar 6, arriving in Chicago Midway.Price includes taxes and charges.From $869, select.

Liberia.$946 per passenger.Departing Sat, Apr 24, returning Sat, May 1.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago Midway on Sat, Apr 24, arriving in Liberia.Inbound indirect flight with Delta, departing from Liberia on Sat, May 1, arriving in Chicago Midway.Price includes taxes and charges.From $946, select.

Liberia.$1,018 per passenger.Departing Mon, Mar 8, returning Sat, Mar 13.Round-trip flight with WestJet and Air Transat.Outbound indirect flight with WestJet, departing from Chicago Midway on Mon, Mar 8, arriving in Liberia.Inbound indirect flight with Air Transat, departing from Liberia on Sat, Mar 13, arriving in Chicago Midway.Price includes taxes and charges.From $1,018, select.

Liberia.$1,038 per passenger.Departing Wed, May 5, returning Mon, May 10.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago Midway on Wed, May 5, arriving in Liberia.Inbound indirect flight with Delta, departing from Liberia on Mon, May 10, arriving in Chicago Midway.Price includes taxes and charges.From $1,038, select.

Find the cheapest month to fly from Chicago Midway to Liberia

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Liberia flights are currently cheapest in November.

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Chicago Midway to Liberia: Alternative routes

Compare routes from Chicago Midway to Liberia below. You may find an airport to fly into that's cheaper, faster, or easier than Liberia.

Chicago to Liberia: Flight information

The things to know before you go.

Cheapest flight found	$494
Cheapest month to fly	November

Finding cheap flights from Chicago Midway to Liberia: Frequently asked questions

How much are round-trip flights from Chicago Midway to Liberia?

The best price we found for a round-trip flight from Chicago Midway to Liberia is $494. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

Which airlines fly direct from Chicago Midway to Liberia?

Currently, there are no airlines that fly direct from Chicago Midway to Liberia. But we found flights with one or more stops from $494.

How many flights are there a week from Chicago Midway to Liberia?

There are no flights flying from Chicago Midway to Liberia, as of August 2026.

When is the cheapest time to fly from Chicago Midway to Liberia?

The cheapest month to fly from Chicago Midway to Liberia is usually November.

Which upcoming date is cheapest to fly from Chicago Midway Airport to Liberia Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Liberia Airport on Sunday, November 15, 2026.

Can I get a direct flight from Chicago Midway Airport to Liberia Airport?

No airlines currently offer direct flights between Chicago Midway Airport and Liberia Airport. Most routes have one or more stops.

How can I find the best flight deal to Liberia?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Liberia but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Liberia?

We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Liberia is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly with from Chicago Midway Airport to Liberia?

Currently, Southwest Airlines offers the cheapest flight tickets to Liberia.

Flying from Chicago Midway Airport (MDW) to Liberia Airport (LIR): what you need to know

Chicago and Liberia are in the same timezone, UTC-6.
Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for hassle-free flying. Be at the airport on time to board your MDW to LIR flight.
You can expect longer lines in popular months such as July. Arriving up to four hours ahead of an international flight and two hours for a domestic departure is a wise move.
We make it a breeze to book a flight with a stopover. To see all your options for tickets from Chicago Midway Airport to Liberia Airport, deselect 'Direct flights only.' Then, choose a flight that has a stop long enough to tour your chosen city. Some great stopovers between MDW and LIR include:
- Atlanta Hartsfield-Jackson Airport
- Houston George Bush Intercntl. Airport
- Houston Hobby Airport

How to find the cheapest flights from Chicago Midway Airport (MDW) to Liberia Airport (LIR)

Currently, $235 is the lowest price we've found for a one-way Chicago Midway Airport to Liberia Airport flight. The best price for a return ticket is $494. Remember that fares may change due to demand at the time of booking.
It's often best to book as early as possible if you want to find cheap tickets from MDW to LIR. That's because airlines adjust prices based on demand, which tends to increase closer to departure.
The 'Whole month' search tool shows you the cheapest flights from Chicago Midway Airport to Liberia Airport throughout the month. It's a great way to find a bargain if your travel dates aren't set in stone.
Save time searching for cheap flights from MDW to LIR by creating a Price Alert. You'll receive an email or push notification on the app when a new low fare is offered.
Tailor your trip using filters. Pick your preferred arrival and departure times, airlines and total journey duration. You can also sort results by 'Best,' 'Fastest' or 'Cheapest' flights from Chicago Midway Airport to Liberia Airport.

Handy information about Chicago Midway Airport (MDW)

The address for MDW is 5700 South Cicero.
When it comes to the on-time performance of Chicago Midway Airport, data shows 76% of flights arrive within the scheduled timeframe.
Central Chicago to Chicago Midway Airport is approximately 16 kilometers. Depending on traffic, it'll take you about 25 minutes to get there if you're driving, ride-sharing or catching a cab.
Taking public transport? Expect a journey time of around 30 minutes.
Have an early flight from Chicago Midway Airport to Liberia Airport? Avoid rushing to the terminal (and enjoy a little extra shut-eye) by picking one of these hotels close to MDW:

Arriving at Liberia Airport (LIR)

Consider staying in a hotel close to LIR if you're on a late Chicago Midway Airport to Liberia Airport flight. Settle into one of these accommodation options and skip the long transfer after landing:
Pick up a Liberia Airport rental car and explore Liberia and beyond with your own wheels. Avis, Europcar and NU Car Rentals are top outlets you can book with here.
Booking your ride from Liberia Airport about two weeks in advance gives you the best chance of locking in a great deal.

Getting from Liberia Airport (LIR) to central Liberia

Liberia Airport to central Liberia has a drive time of about 20 minutes. It's approximately 13 kilometers away.
If you're traveling by public transport, expect a journey of around 30 minutes.

When to fly to Liberia Airport (LIR)

April is the busiest month for flights from Chicago Midway Airport to Liberia Airport. To escape the crowds, travel to Liberia in September.
Lock in your flight from Chicago Midway Airport to Liberia Airport for April if you want to go to Liberia during its warmest month. Expect temperatures of between 22ºC (72ºF) and 35ºC (95ºF).
January sees average temperatures of between 21ºC (70ºF) and 32ºC (90ºF). Search for cheap tickets from MDW to LIR around that time if you want to travel when it's cooler.

Explore more of Costa Rica

Liberia is always a good idea, but there are so many other corners of Costa Rica waiting to be discovered. Around 161 kilometers south-east of Liberia, a visit to San Jose will keep your itinerary packed. Don't miss top attractions like National Park (Parque Nacional), Central Park (Parque Central) and Precolumbian Gold Museum.
If you're eager to discover another major destination in Costa Rica, head for Limon, about 274 kilometers east of Liberia. Veragua Rainforest Park, Playa Bonita and Playa Los Baños are among its highlights.