What are the cheapest airlines to fly from Chicago to Kailua one-way?

To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $283. Hawaiian Airlines flights start at $286 while deals on Alaska Airlines start at $293 one-way.

What are the cheapest flights from Chicago to Kailua?

On average you can expect to pay $2,284 for a flight from Chicago to Kailua. The cheapest flight overall is $277 while the most popular route, (Chicago O'Hare Intl - Honolulu) is currently priced at $436.

What are the most popular airlines that fly from Chicago to Kailua?

American Airlines, Alaska Airlines and Delta are the most popular airlines when flying from Chicago to Kailua.

How far in advance should I book a flight from Chicago to Kailua?

Find a great deal and save up to 37% by booking at least 54 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Kailua within the next two weeks, with the cheapest ticket starting at $685.

What is the cheapest month to fly from Chicago to Kailua?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, February can be a great choice for travel to Kailua. Flights to Kailua from Chicago in February are about $770 on average during February, but can be found for as low as $421.

Can I find deals for flights from Chicago to Kailua that include hotel bookings?

Yes. In addition to deals on Chicago to Kailua flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Chicago to Kailua?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kailua.

Can I find deals for business class flights from Chicago to Kailua?

Yes. Cheapflights offers flight deals from Chicago to Kailua by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$282+ Flights from Chicago to Kailua

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Cheapflights Tip: The best prices from Chicago to Kailua are usually found in February or January, booked 53 days in advance, depart on a Thursday or Tuesday and return on a Monday

Cheap flight deals from Chicago to Kailua

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$513 (Delta)
One-way from	$283 (Delta)
Popular in	December
Cheapest in	February
Average price	$722

Provider with most accurate pricing for Chicago (CHI)-Honolulu flight deals.

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Provider most trusted by Cheapflights users for Chicago (CHI)-Honolulu flights.

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From Chicago (CHI) to Kailua

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One-way flight from Chicago (CHI) to Kailua

Search Deals

Highest demand for flights based on searches. 3% potential increase in price ($26 potential increase over avg. RT price).

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Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).

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Average for round-trip flights in May 2025

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Find flight deals from Chicago to Kailua

Cheapest flights from Chicago to Kailua
Explore the most affordable flight options available from Chicago to Kailua. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Mon 5/267:10 amORD - HNL

1 stop12h 34mDelta

Wed 6/43:09 pmHNL - ORD

1 stop13h 42mDelta

Deal found 5/1

$513

Fri 6/137:18 pmORD - HNL

1 stop31h 57mAlaska Airlines

Tue 6/178:00 amHNL - ORD

1 stop30h 42mAlaska Airlines

Deal found 4/30

$519

Mon 9/15:00 amORD - HNL

1 stop14h 10mAmerican Airlines

Mon 9/19:11 pmHNL - ORD

1 stop10h 16mAmerican Airlines

Deal found 4/30

$520

Sun 5/259:20 amMDW - HNL

2 stops16h 24mDelta

Mon 6/21:10 pmHNL - MDW

2 stops14h 26mDelta

Deal found 4/30

$524

Wed 9/39:20 pmMDW - HNL

1 stop18h 00mSouthwest

Tue 9/99:05 pmHNL - MDW

2 stops11h 40mSouthwest

Deal found 5/1

$529

Sun 6/16:10 amORD - HNL

1 stop19h 30mMultiple Airlines

Sat 6/73:35 pmHNL - ORD

1 stop26h 20mMultiple Airlines

Deal found 4/30

$559

Wed 10/229:00 amORD - HNL

1 stop11h 30mHawaiian Airlines

Wed 10/291:25 pmHNL - ORD

1 stop10h 39mHawaiian Airlines

Deal found 4/30

$573

Sun 6/110:18 amMDW - HNL

3 stops37h 52mMultiple Airlines

Sat 6/73:35 pmHNL - MDW

2 stops42h 21mMultiple Airlines

Deal found 5/1

$622

Wed 8/66:22 pmORD - HNL

1 stop24h 42mUnited Airlines

Mon 8/111:30 pmHNL - ORD

1 stop16h 57mUnited Airlines

Deal found 5/1

$681

Best flights from Chicago to Kailua
Discover carefully curated flight deals from Chicago to Kailua that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 1, 2025.

Mon 5/267:10 amORD - HNL

1 stop12h 34mDelta

Wed 6/43:09 pmHNL - ORD

1 stop13h 42mDelta

Deal found 5/1

$513

Fri 6/137:18 pmORD - HNL

1 stop31h 57mAlaska Airlines

Tue 6/178:00 amHNL - ORD

1 stop30h 42mAlaska Airlines

Deal found 4/30

$519

Sat 5/311:33 pmORD - HNL

1 stop12h 38mAmerican Airlines

Thu 6/511:26 pmHNL - ORD

1 stop12h 51mAmerican Airlines

Deal found 5/1

$547

Sun 6/16:10 amORD - HNL

1 stop19h 30mMultiple Airlines

Sat 6/73:35 pmHNL - ORD

1 stop26h 20mMultiple Airlines

Deal found 4/30

$559

Wed 7/97:20 amORD - HNL

1 stop16h 49mUnited Airlines

Thu 7/178:30 amHNL - ORD

1 stop16h 15mUnited Airlines

Deal found 4/30

$685

Mon 5/56:15 amORD - HNL

2 stops15h 10mSouthwest

Mon 5/129:00 pmHNL - ORD

2 stops14h 45mSouthwest

Deal found 4/30

$711

Sun 5/259:20 amMDW - HNL

2 stops16h 24mDelta

Mon 6/21:10 pmHNL - MDW

2 stops14h 26mDelta

Deal found 4/30

$524

Sun 6/110:18 amMDW - HNL

3 stops37h 52mMultiple Airlines

Sat 6/73:35 pmHNL - MDW

2 stops42h 21mMultiple Airlines

Deal found 5/1

$622

Fri 5/911:55 amMDW - HNL

1 stop14h 05mSouthwest

Sun 5/1112:10 pmHNL - MDW

1 stop12h 05mSouthwest

Deal found 5/1

$717

Last-minute flights from Chicago to Kailua
Discover last-minute flight deals from Chicago to Kailua. Data last updated May 1, 2025 and is based on user searches.

Fri 5/26:15 amORD - HNL

2 stops15h 10mSouthwest

Thu 5/88:10 amHNL - ORD

1 stop10h 30mSouthwest

Deal found 4/30

$705

Wed 5/77:19 pmORD - HNL

1 stop33h 37mAlaska Airlines

Mon 5/122:48 pmHNL - ORD

1 stop28h 11mAlaska Airlines

Deal found 4/30

$585

Wed 5/76:00 amMDW - HNL

1 stop12h 29mDelta

Mon 5/123:00 pmHNL - MDW

1 stop13h 40mDelta

Deal found 4/29

$657

Wed 5/79:30 amORD - HNL

Nonstop9h 13mUnited Airlines

Wed 5/145:15 pmHNL - ORD

Nonstop8h 10mUnited Airlines

Deal found 4/30

$1,219

Fri 5/911:55 amMDW - HNL

1 stop14h 05mSouthwest

Sun 5/1112:10 pmHNL - MDW

1 stop12h 05mSouthwest

Deal found 5/1

$717

Sun 5/115:30 amORD - HNL

1 stop12h 59mDelta

Sat 5/2410:30 pmHNL - ORD

1 stop13h 55mDelta

Deal found 4/30

$604

Sun 5/119:30 amORD - HNL

Nonstop9h 13mMultiple Airlines

Sat 5/248:00 amHNL - ORD

1 stop10h 59mMultiple Airlines

Deal found 4/30

$1,063

Mon 5/198:40 amORD - HNL

2 stops19h 49mMultiple Airlines

Thu 5/228:55 amHNL - ORD

2 stops33h 10mMultiple Airlines

Deal found 4/30

$584

Sun 5/259:20 amMDW - HNL

2 stops16h 24mDelta

Mon 6/21:10 pmHNL - MDW

2 stops14h 26mDelta

Deal found 4/30

$524

Mon 5/267:10 amORD - HNL

1 stop12h 34mDelta

Wed 6/43:09 pmHNL - ORD

1 stop13h 42mDelta

Deal found 5/1

$513

Wed 5/283:15 pmORD - HNL

1 stop10h 56mAmerican Airlines

Sat 5/316:20 amHNL - ORD

1 stop11h 12mAmerican Airlines

Deal found 4/30

$547

Thu 5/2910:00 amORD - HNL

1 stop14h 10mAlaska Airlines

Thu 6/511:45 pmHNL - ORD

1 stop14h 10mAlaska Airlines

Deal found 5/1

$525

One-way flights from Chicago to Kailua
Search for one-way flight options from Chicago to Kailua. Find affordable one-way fares based on user searches. Data last updated May 1, 2025.

Mon 6/27:15 amORD - HNL

1 stop33h 40mDelta

Deal found 5/1

$283

Thu 6/53:17 pmORD - HNL

1 stop12h 50mHawaiian Airlines

Deal found 4/30

$286

Thu 5/296:00 amORD - HNL

2 stops21h 20mAlaska Airlines

Deal found 4/29

$293

Sun 6/83:12 pmORD - HNL

1 stop11h 43mAmerican Airlines

Deal found 5/1

$302

Wed 5/76:00 amMDW - HNL

1 stop12h 29mDelta

Deal found 4/30

$329

Thu 7/36:20 pmORD - HNL

1 stop24h 39mUnited Airlines

Deal found 4/29

$343

Fri 5/166:15 amORD - HNL

2 stops15h 10mSouthwest

Deal found 4/30

$362

Sun 5/410:45 pmMDW - HNL

1 stop18h 05mSouthwest

Deal found 4/30

$372

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Kailua that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 5/26

7:10 am-2:44 pm

1 stop12h 34m

Honolulu

Wed 6/4

3:09 pm-9:51 am

1 stop13h 42m

$513

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Fri 6/13

7:18 pm-10:15 pm

1 stop31h 57m

Honolulu

Tue 6/17

8:00 am-7:42 pm

1 stop30h 42m

$519

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 9/1

5:00 am-2:10 pm

1 stop14h 10m

Honolulu

Mon 9/1

9:11 pm-12:27 pm

1 stop10h 16m

$520

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 5/25

9:20 am-8:44 pm

2 stops16h 24m

Honolulu

Mon 6/2

1:10 pm-8:36 am

2 stops14h 26m

$524

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 9/3

9:20 pm-10:20 am

1 stop18h 00m

Honolulu

Tue 9/9

9:05 pm-1:45 pm

2 stops11h 40m

$529

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sun 6/1

6:10 am-8:40 pm

1 stop19h 30m

Honolulu

Sat 6/7

3:35 pm-10:55 pm

1 stop26h 20m

$559

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 10/22

9:00 am-3:30 pm

1 stop11h 30m

Honolulu

Wed 10/29

1:25 pm-5:04 am

1 stop10h 39m

$573

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 6/1

10:18 am-7:10 pm

3 stops37h 52m

Honolulu

Sat 6/7

3:35 pm-2:56 pm

2 stops42h 21m

$622

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 8/6

6:22 pm-2:04 pm

1 stop24h 42m

Honolulu

Mon 8/11

1:30 pm-11:27 am

1 stop16h 57m

$681

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 10/27

7:30 am-7:20 pm

1 stop16h 50m

$282

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 17 results

Best time to book a flight from Chicago to Kailua

Have a flexible travel schedule? Discover the best time to fly to Kailua from Chicago with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Kailua

How far ahead should I book a flight from Chicago to Kailua?

To ensure you get the cheapest price possible for a flight from Chicago to Kailua, you should look to book at least 53 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Kailua?

Currently, November is the cheapest month in which you can book a flight from Chicago to Kailua (average of $469). Flying from Chicago to Kailua in June is currently the most expensive (average of $687). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to K4I?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Kailua as you normally would.

What is the cheapest day to fly from Chicago to Kailua?

Travelers seeking maximum savings on their Chicago to Kailua flight should consider departing on Friday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Kailua

The most flights from CHI to K4I are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Kailua by month

In terms of precipitation, rainfall in Kailua ranges from 0.3 - 3.2 inches per month. December is typically the wettest month, when rainfall can reach 3.2 in. June is typically the driest time to visit Kailua when rainfall is around 0.3 in.

Temperature in Kailua by month

If weather is an important factor for your trip to Kailua, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 73.4 F).

Reviews of airlines servicing Kailua

Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to Kailua to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Alaska Airlines

8.0

Very good

9,972 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Alaska Airlines

8.0

Very good

9,972 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Southwest

8.0

Very good

4,293 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Delta

8.0

Very good

7,934 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Hawaiian Airlines

7.9

Good

2,409 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

United Airlines

7.4

Good

8,696 reviews

Alaska Airlines

8.0

Very good

9,972 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

What are the cheapest airlines to fly from Chicago to Kailua one-way?
To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $283. Hawaiian Airlines flights start at $286 while deals on Alaska Airlines start at $293 one-way.
What are the cheapest flights from Chicago to Kailua?
On average you can expect to pay $2,284 for a flight from Chicago to Kailua. The cheapest flight overall is $277 while the most popular route, (Chicago O'Hare Intl - Honolulu) is currently priced at $436.
Can I find deals for flights from Chicago to Kailua that include hotel bookings?
Yes. In addition to deals on Chicago to Kailua flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to Kailua?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kailua.
Can I find deals for business class flights from Chicago to Kailua?
Yes. Cheapflights offers flight deals from Chicago to Kailua by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Chicago to Kailua?
Currently, November is the cheapest month in which you can book a flight from Chicago to Kailua (average of $469). Flying from Chicago to Kailua in June is currently the most expensive (average of $687). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Chicago to Kailua

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O'Hare Intl to Waimea (Big Island) flights

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Evansville to Lihue flights

St. Louis to Waimea (Big Island) flights

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Dubuque to Honolulu flights

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Decatur to Honolulu flights

Springfield to Kahului flights

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Moline to Hilo flights

Bloomington to Lihue flights

Champaign to Honolulu flights

Moline to Kailua-Kona flights

Champaign to Kailua-Kona flights

Top 6 airlines flying from Chicago to Kailua

Airline	Cheapest	Average	Flexibility	On-time
Hawaiian Airlines	Cheapest$369	Average$847	FlexibilityNo cancel fee	On-time85%
Delta	Cheapest$396	Average$706	FlexibilityNo cancel fee	On-timeN/A
Alaska Airlines	Cheapest$418	Average$648	FlexibilityNo cancel fee	On-time75%
American Airlines	Cheapest$421	Average$661	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$522	Average$753	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$796	Average$1,126	FlexibilityNo cancel fee	On-time69%

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$282+ Cheap flights from Chicago (CHI) to Kailua, HI

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Kailua with Cheapflights

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3. Compare prices and book

Cheapflights Tip: The best prices from Chicago to Kailua are usually found in February or January, booked 53 days in advance, depart on a Thursday or Tuesday and return on a Monday

Cheap flight deals from Chicago to Kailua

Keep the following information in mind while searching for Chicago to Kailua flight deals. Data was last updated May 1, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Chicago to Kailua

Cheapest flights from Chicago to KailuaExplore the most affordable flight options available from Chicago to Kailua. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Explore the most affordable flight options available from Chicago to Kailua. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Kailua that are best for you.

Best time to book a flight from Chicago to Kailua

Have a flexible travel schedule? Discover the best time to fly to Kailua from Chicago with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Kailua

How far ahead should I book a flight from Chicago to Kailua?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Kailua. Price data was last updated on April 25, 2025.

What is the cheapest month to book a flight from Chicago to Kailua?

What is the cheapest time of day to fly from CHI to K4I?

Find hourly flight availability from Chicago to Kailua. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

What is the cheapest day to fly from Chicago to Kailua?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Kailua. Price data was last updated on December 16, 2024.

Weekly flight availability from Chicago to Kailua

Explore weekly flight availability from Chicago to Kailua. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 1, 2025.

Rainfall in Kailua by month

Plan your trip to Kailua by taking into account the average rainfall totals by month.

Temperature in Kailua by month

Plan your trip to Kailua by taking into account the average temperature totals by month.

Reviews of airlines servicing Kailua

Get insights into the airlines that provide service to Kailua. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kailua. Reviews last updated May 1, 2025.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Kailua. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What are the cheapest airlines to fly from Chicago to Kailua one-way?

What are the cheapest flights from Chicago to Kailua?

Can I find deals for flights from Chicago to Kailua that include hotel bookings?

How can I find direct flights from Chicago to Kailua?

Can I find deals for business class flights from Chicago to Kailua?

What is the cheapest month to book a flight from Chicago to Kailua?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Kailua

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Chicago to Kailua

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Cheapest flights from Chicago to Kailua
Explore the most affordable flight options available from Chicago to Kailua. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.