Cheap flights from Chicago to Praia

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Flight deals from Chicago to Praia

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Praia Airport? If you want to travel next month, round-trip fares start from $1,220. Find the lowest prices on one-way and round-trip tickets right here.

Praia.$952 per passenger.Departing Fri, Oct 2, returning Fri, Oct 16.Round-trip flight with Icelandair and Cabo Verde Airlines.Outbound indirect flight with Icelandair, departing from Chicago O'Hare International on Fri, Oct 2, arriving in Praia.Inbound indirect flight with Cabo Verde Airlines, departing from Praia on Fri, Oct 16, arriving in Chicago O'Hare International.Price includes taxes and charges.From $952, select.

Praia.$958 per passenger.Departing Wed, Oct 28, returning Fri, Nov 13.Round-trip flight with Icelandair and Cabo Verde Airlines.Outbound indirect flight with Icelandair, departing from Chicago O'Hare International on Wed, Oct 28, arriving in Praia.Inbound indirect flight with Cabo Verde Airlines, departing from Praia on Fri, Nov 13, arriving in Chicago O'Hare International.Price includes taxes and charges.From $958, select.

Praia.$958 per passenger.Departing Fri, Sep 18, returning Fri, Oct 2.Round-trip flight with jetBlue and Cabo Verde Airlines.Outbound indirect flight with jetBlue, departing from Chicago O'Hare International on Fri, Sep 18, arriving in Praia.Inbound indirect flight with Cabo Verde Airlines, departing from Praia on Fri, Oct 2, arriving in Chicago Rockford.Price includes taxes and charges.From $958, select.

Praia.$1,037 per passenger.Departing Wed, Nov 4, returning Fri, Nov 20.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Wed, Nov 4, arriving in Praia.Inbound indirect flight with TAP Air Portugal, departing from Praia on Fri, Nov 20, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,037, select.

Praia.$1,050 per passenger.Departing Thu, Sep 3, returning Thu, Sep 10.Round-trip flight with Porter Airlines and TAP Air Portugal.Outbound indirect flight with Porter Airlines, departing from Chicago O'Hare International on Thu, Sep 3, arriving in Praia.Inbound indirect flight with TAP Air Portugal, departing from Praia on Thu, Sep 10, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,050, select.

Praia.$1,097 per passenger.Departing Thu, Aug 27, returning Thu, Sep 3.Round-trip flight with jetBlue and TAP Air Portugal.Outbound indirect flight with jetBlue, departing from Chicago O'Hare International on Thu, Aug 27, arriving in Praia.Inbound indirect flight with TAP Air Portugal, departing from Praia on Thu, Sep 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,097, select.

Praia.$1,107 per passenger.Departing Fri, Jan 15, returning Fri, Jan 22.Round-trip flight with jetBlue and easyJet.Outbound indirect flight with jetBlue, departing from Chicago O'Hare International on Fri, Jan 15, arriving in Praia.Inbound indirect flight with easyJet, departing from Praia on Fri, Jan 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,107, select.

Praia.$1,192 per passenger.Departing Mon, May 3, returning Mon, May 10.Round-trip flight with Icelandair and TAP Air Portugal.Outbound indirect flight with Icelandair, departing from Chicago O'Hare International on Mon, May 3, arriving in Praia.Inbound indirect flight with TAP Air Portugal, departing from Praia on Mon, May 10, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,192, select.

Praia.$1,195 per passenger.Departing Sun, Apr 18, returning Sun, May 9.Round-trip flight with Icelandair and TAP Air Portugal.Outbound indirect flight with Icelandair, departing from Chicago O'Hare International on Sun, Apr 18, arriving in Praia.Inbound indirect flight with TAP Air Portugal, departing from Praia on Sun, May 9, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,195, select.

Praia.$1,211 per passenger.Departing Fri, Dec 11, returning Thu, Dec 17.Round-trip flight with jetBlue and TAP Air Portugal.Outbound indirect flight with jetBlue, departing from Chicago O'Hare International on Fri, Dec 11, arriving in Praia.Inbound indirect flight with TAP Air Portugal, departing from Praia on Thu, Dec 17, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,211, select.

Praia.$1,219 per passenger.Departing Tue, Feb 16, returning Sat, Feb 27.Round-trip flight with Icelandair and easyJet.Outbound indirect flight with Icelandair, departing from Chicago O'Hare International on Tue, Feb 16, arriving in Praia.Inbound indirect flight with easyJet, departing from Praia on Sat, Feb 27, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,219, select.

Praia.$1,220 per passenger.Departing Mon, Aug 24, returning Mon, Aug 31.Round-trip flight with jetBlue and TAP Air Portugal.Outbound indirect flight with jetBlue, departing from Chicago O'Hare International on Mon, Aug 24, arriving in Praia.Inbound indirect flight with TAP Air Portugal, departing from Praia on Mon, Aug 31, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,220, select.

Praia.$1,432 per passenger.Departing Wed, Jul 8, returning Wed, Jul 15.Round-trip flight with TAP Air Portugal and easyJet.Outbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Wed, Jul 8, arriving in Praia.Inbound indirect flight with easyJet, departing from Praia on Wed, Jul 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,432, select.

Praia.$1,623 per passenger.Departing Wed, Jul 22, returning Tue, Aug 4.Round-trip flight with jetBlue and TAP Air Portugal.Outbound indirect flight with jetBlue, departing from Chicago O'Hare International on Wed, Jul 22, arriving in Praia.Inbound indirect flight with TAP Air Portugal, departing from Praia on Tue, Aug 4, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,623, select.

Praia.$1,653 per passenger.Departing Fri, Mar 19, returning Mon, Mar 22.Round-trip flight with jetBlue and transavia.Outbound indirect flight with jetBlue, departing from Chicago O'Hare International on Fri, Mar 19, arriving in Praia.Inbound indirect flight with transavia, departing from Praia on Mon, Mar 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,653, select.

Praia.$2,038 per passenger.Departing Mon, Jun 7, returning Mon, Jun 14.Round-trip flight with Lufthansa and TAP Air Portugal.Outbound indirect flight with Lufthansa, departing from Chicago O'Hare International on Mon, Jun 7, arriving in Praia.Inbound indirect flight with TAP Air Portugal, departing from Praia on Mon, Jun 14, arriving in Chicago O'Hare International.Price includes taxes and charges.From $2,038, select.

Find the cheapest month to fly from Chicago to Praia

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

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Chicago to Praia: Alternative routes

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

Praia

1km from central Praia

ClosestCheapest

from $952

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Vila Do Maio

52km from central Praia

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Chicago to Praia: Flight information

The things to know before you go.

Cheapest flight found	$952
Cheapest month to fly	October

Finding cheap flights from Chicago to Praia: Frequently asked questions

How much are round-trip flights from Chicago to Praia?

The best price we found for a round-trip flight from Chicago to Praia is $952. 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 to Praia?

Currently, there are no airlines that fly direct from Chicago to Praia. But we found flights with one stop from $952.

How many flights are there a week from Chicago to Praia?

There are no flights flying from Chicago to Praia, as of July 2026.

When is the cheapest time to fly from Chicago to Praia?

The cheapest month to fly from Chicago to Praia is usually October.

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

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Praia Airport on Friday, October 2, 2026.

Can I get a direct flight from Chicago to Praia Airport?

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

How can I find the best flight deal to Praia?

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 Praia 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 Praia?

We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Praia 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 to Praia?

The cheapest airline that flies to Praia is Icelandair.

Flying from Chicago to Praia Nelson Mandela International Airport (RAI): What you need to know

The timezone in Praia is UTC-1, which is five hours ahead of Chicago. Praia Nelson Mandela International Airport is located in Praia.
Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules to live by. Be at the airport with enough time to board your flight from Chicago to RAI.
If you're getting away during a popular month like July, make your way to the airport even earlier. It's smart to arrive up to four hours before international flights and two hours ahead of a domestic departure. Check-in and security lines will be longer during peak periods like Christmas, New Year and spring break.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

ORD is about 27 kilometers from central Chicago. If you're catching a cab, driving or ride-sharing from the center, it'll take 30 minutes or so to get there, depending on the traffic. If you're planning to take public transport, expect the travel time to be around 45 minutes.
Have an early flight from Chicago to Praia Nelson Mandela International Airport? Avoid the stress of rushing to the terminal (and catch some extra z's) by picking one of these stays close to Chicago O'Hare International Airport:
When it comes to Chicago O'Hare International Airport's on-time performance, 70% of flights arrive within the expected time frame.
ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

You can arrive at MDW from central Chicago in about 25 minutes by car, depending on traffic conditions. The ride by public transport will take roughly 30 minutes to cover the 16 kilometers or so.
Flying off with the first light? Think about staying at one of these hotels near Chicago Midway International Airport the day before your Chicago to RAI flight:
76% of flights leaving Chicago Midway International Airport make it to their destination as expected.
The street address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

RFD is around 145 kilometers from central Chicago. The drive from the city center to the terminal takes about 1 hour 40 minutes. If you're thinking about taking public transport, expect a journey time of around 2 hours.
Sleep a little longer and still make your Chicago to Praia Nelson Mandela International Airport flight with time to spare. These accommodation options near Chicago Rockford International Airport make departure day a breeze if you're setting off early:
The on-time performance rating of RFD is 71%. To put it simply, that's how often flights that depart this airport arrive at their final stop as planned.
Chicago Rockford International Airport is located at 2 Airport Cir.

About Praia Nelson Mandela International Airport (RAI)

Have a late flight from Chicago to Praia Nelson Mandela International Airport? Don't let it leave you bleary-eyed. Stay at one of these hotels near RAI and hit the lights earlier:
Lock in the best rate by booking your vehicle around two weeks before your Chicago to Praia Nelson Mandela International Airport flight.

Getting from Praia Nelson Mandela International Airport (RAI) to central Praia

Praia Nelson Mandela International Airport is roughly 3 kilometers from central Praia. The time it takes to get to the center in a car rental or cab depends on the time of day. Do a little research before your trip.
Traveling by public transport typically takes 20 minutes.

How to find the cheapest flights from Chicago to Praia Nelson Mandela International Airport (RAI)

At the moment, $450 is the best price we've found for a one-way ticket from Chicago to Praia Nelson Mandela International Airport. The cheapest price for a return flight is $952. Remember fares can change due to demand at the time of booking.
Booking early is often the key to scoring a cheap flight from Chicago to RAI. Flight prices rise as demand increases, so the closer your departure date, the more expensive your ticket may be.
The 'Whole month' search tool will show you the cheapest Chicago to Praia Nelson Mandela International Airport tickets across each month. It's an easy way to snap up a bargain if your travel dates aren't set in stone.
There's no need to check every day to find out if fares have dropped when you set up a Price Alert. We'll notify you when a lower fare pops up on plane tickets from Chicago to RAI.
Filters make it easier to land a deal on your flight from Chicago to Praia Nelson Mandela International Airport. Choose the flight times, carriers and stops that look good to you. Then sort the results by 'Cheapest' to find the lowest price right away.

The best time to fly from Chicago to Praia Nelson Mandela International Airport (RAI)

January is when most people book flights from Chicago to Praia Nelson Mandela International Airport (RAI). Plan your visit to Praia in December for a more low-key escape.
The warmest month in Praia is October, with temperatures ranging between 24ºC (75ºF) and 30ºC (86ºF). Book your Chicago to RAI plane ticket then if that's your definition of good weather.
Look for cheap tickets from Chicago to Praia Nelson Mandela International Airport in March if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between 19ºC (66ºF) and 26ºC (79ºF).

More about Praia

When it comes to looking for somewhere to rest your head, you'll find the top stays in Praia right here. Check out these hotels once you've booked your flight from Chicago to Praia Nelson Mandela International Airport:
Prainha Beach and Praia de Gamboa Beach are just a couple of the leading attractions to put on your Praia must-do list. Keep the sightseeing going at Casa da Arte.

Explore more of Cape Verde

You've seen Praia, now it's time to discover more of Cape Verde. Journey about 274 kilometers northwest to Mindelo to check off its leading attractions. From Piscinas Naturais da Fajã Grande to Praia da Laginha and Ponta Joao Ribeiro, your itinerary will be busy.
Santa Maria is another sought-after destination in Cape Verde and is around 193 kilometers north of Praia. No trip is complete without visiting Ponta Preta Beach, Kite Beach Coastline and Praia de Santa Maria.