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Cheap flights from Chicago to Oaxaca from $109

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Oaxaca departing on 2/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Oaxaca

Cheap round-trip flights

Enter your travel dates to find the best prices.
Viva Logo
1:20 am - 4:25 pm
ORD
-
OAX
15h 05m
1 stop
Viva Logo
1:10 pm - 11:25 pm
OAX
-
ORD
10h 15m
1 stop
$285Viva
Mon, Feb 16 - Tue, Feb 24
Volaris Logo
1:40 am - 8:13 am
ORD
-
OAX
7h 33m
1 stop
Volaris Logo
7:34 pm - 5:52 am
OAX
-
ORD
9h 18m
1 stop
$291Volaris
Tue, Apr 14 - Mon, Apr 20
Volaris Logo
2:19 am - 8:38 am
ORD
-
OAX
7h 19m
1 stop
Volaris Logo
7:34 pm - 5:52 am
OAX
-
ORD
9h 18m
1 stop
$294Volaris
Thu, Apr 16 - Tue, Apr 21
Volaris Logo
11:58 pm - 7:19 am
ORD
-
OAX
7h 21m
1 stop
Volaris Logo
8:56 am - 11:06 pm
OAX
-
ORD
13h 10m
1 stop
$300Volaris
Sun, Mar 1 - Wed, Mar 18
Volaris Logo
11:58 pm - 7:19 am
ORD
-
OAX
7h 21m
1 stop
Volaris Logo
8:56 am - 10:06 pm
OAX
-
ORD
13h 10m
1 stop
$302Volaris
Sun, Feb 22 - Fri, Feb 27
Multiple Airlines Logo
11:59 pm - 7:35 am
ORD
-
OAX
8h 36m
1 stop
Multiple Airlines Logo
4:55 pm - 12:45 am
OAX
-
ORD
6h 50m
1 stop
$312Multiple Airlines
Sat, Mar 14 - Wed, Mar 18
Delta Logo
6:00 am - 7:00 pm
MDW
-
OAX
13h 00m
2 stops
Delta Logo
7:56 am - 10:31 pm
OAX
-
MDW
13h 35m
2 stops
$483Delta
Wed, Mar 4 - Wed, Mar 11
Delta Logo
6:00 am - 7:00 pm
MDW
-
OAX
13h 00m
2 stops
Delta Logo
10:12 am - 10:31 pm
OAX
-
MDW
11h 19m
2 stops
$497Delta
Wed, Mar 4 - Wed, Mar 11
Aeromexico Logo
6:00 am - 4:40 pm
MDW
-
OAX
11h 40m
2 stops
Aeromexico Logo
10:30 am - 10:28 pm
OAX
-
MDW
10h 58m
2 stops
$509Aeromexico
Fri, Apr 17 - Fri, Apr 24
Frontier Logo
5:16 pm - 4:12 pm
MDW
-
OAX
22h 56m
2 stops
Frontier Logo
8:40 am - 9:45 pm
OAX
-
MDW
36h 05m
2 stops
$628Frontier
Thu, Mar 5 - Fri, Mar 13

Volaris flights from Chicago to Oaxaca

Our best Volaris deals on Chicago to Oaxaca flight tickets
Volaris
Apr 14
ORD1:40 amChicago O'Hare Intl
7h 33m
1 stop
OAX8:13 amOaxaca Xoxocotlan
Apr 20
OAX7:34 pmOaxaca Xoxocotlan
9h 18m
1 stop
ORD5:52 amChicago O'Hare Intl
$291
Volaris
Apr 16
ORD2:19 amChicago O'Hare Intl
7h 19m
1 stop
OAX8:38 amOaxaca Xoxocotlan
Apr 21
OAX7:34 pmOaxaca Xoxocotlan
9h 18m
1 stop
ORD5:52 amChicago O'Hare Intl
$294
Volaris
Mar 1
ORD11:58 pmChicago O'Hare Intl
7h 21m
1 stop
OAX7:19 amOaxaca Xoxocotlan
Mar 18
OAX8:56 amOaxaca Xoxocotlan
13h 10m
1 stop
ORD11:06 pmChicago O'Hare Intl
$300

Viva flights from Chicago to Oaxaca

Our best Viva deals on Chicago to Oaxaca flight tickets
Viva
Feb 16
ORD1:20 amChicago O'Hare Intl
15h 05m
1 stop
OAX4:25 pmOaxaca Xoxocotlan
Feb 24
OAX1:10 pmOaxaca Xoxocotlan
10h 15m
1 stop
ORD11:25 pmChicago O'Hare Intl
$285
Viva
Mar 14
ORD6:05 pmChicago O'Hare Intl
22h 05m
2 stops
OAX3:10 pmOaxaca Xoxocotlan
Mar 18
OAX1:10 pmOaxaca Xoxocotlan
10h 25m
1 stop
ORD12:35 amChicago O'Hare Intl
$346
Viva
Mar 10
ORD2:05 amChicago O'Hare Intl
11h 15m
1 stop
OAX12:20 pmOaxaca Xoxocotlan
Mar 14
OAX1:10 pmOaxaca Xoxocotlan
10h 25m
1 stop
ORD12:35 amChicago O'Hare Intl
$347

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Oaxaca that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 1, 2026.
Use the filters below to find and compare flights from Chicago to Oaxaca that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Mon 2/16

1:20 am-4:25 pm

1 stop15h 05m

Oaxaca Xoxocotlan

Tue 2/24

1:10 pm-11:25 pm

1 stop10h 15m

$285

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 4/14

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Mon 4/20

7:34 pm-5:52 am

1 stop9h 18m

$291

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Thu 4/16

2:19 am-8:38 am

1 stop7h 19m

Oaxaca Xoxocotlan

Tue 4/21

7:34 pm-5:52 am

1 stop9h 18m

$294

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 3/1

11:58 pm-7:19 am

1 stop7h 21m

Oaxaca Xoxocotlan

Wed 3/18

8:56 am-11:06 pm

1 stop13h 10m

$300

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 2/22

11:58 pm-7:19 am

1 stop7h 21m

Oaxaca Xoxocotlan

Fri 2/27

8:56 am-10:06 pm

1 stop13h 10m

$302

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 3/14

11:59 pm-7:35 am

1 stop8h 36m

Oaxaca Xoxocotlan

Wed 3/18

4:55 pm-12:45 am

1 stop6h 50m

$312

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 3/4

6:00 am-7:00 pm

2 stops13h 00m

Oaxaca Xoxocotlan

Wed 3/11

7:56 am-10:31 pm

2 stops13h 35m

$483

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 3/4

6:00 am-7:00 pm

2 stops13h 00m

Oaxaca Xoxocotlan

Wed 3/11

10:12 am-10:31 pm

2 stops11h 19m

$497

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Fri 4/17

6:00 am-4:40 pm

2 stops11h 40m

Oaxaca Xoxocotlan

Fri 4/24

10:30 am-10:28 pm

2 stops10h 58m

$509

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Thu 3/5

5:16 pm-4:12 pm

2 stops22h 56m

Oaxaca Xoxocotlan

Fri 3/13

8:40 am-9:45 pm

2 stops36h 05m

$628

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Oaxaca from

How to get the cheapest flight ticket from Chicago to Oaxaca

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and Oaxaca?

What is the cheapest month to fly to Oaxaca?

In general, September is the cheapest month to fly from Chicago to Oaxaca. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $375. If you are unable to visit Oaxaca during the month of September, then departing from Chicago during the month August is also very affordable. Most momondo users find prices during this month for around $383.

How far in advance should I book a flight to Oaxaca?

You are more likely to see cheaper flights to Oaxaca from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Oaxaca for around $545 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Oaxaca from Chicago for as low as $297 on momondo.

How have Chicago to Oaxaca flight prices changed over time?

As of February 2026, prices for Chicago to Oaxaca flights are approximately 26% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Oaxaca

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Oaxaca according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Oaxaca (CHI to OAX) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Oaxaca

Fastest flight time

7h 21m

Direct flights

None
The fastest flight from Chicago to Oaxaca takes 7h 21m
There are no direct flights from Chicago to Oaxaca. There are no popular flight routes from Chicago to Oaxaca.
Search flight deals

  • How far is Chicago to Oaxaca Xoxocotlan by plane?

    A flight from Chicago to Oaxaca Xoxocotlan will travel around 1795.6 mi. In terms of flight time, this usually takes a little over 7h 21m.

  • When did momondo last update prices for flights from Chicago to Oaxaca Xoxocotlan Airport?

    Prices for flights from Chicago to Oaxaca Xoxocotlan Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago to Oaxaca Xoxocotlan Airport?

  • How old do you have to be to fly from Chicago to Oaxaca Xoxocotlan Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Oaxaca Xoxocotlan Airport.

  • What documentation or ID do you need to fly to Oaxaca Xoxocotlan Airport?

    The travel and health documents required for your trip to Oaxaca Xoxocotlan Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Oaxaca Xoxocotlan Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Chicago to Oaxaca?

Best airlines flying from Chicago to Oaxaca

Compare and see reviews for airlines that fly from Chicago to Oaxaca with momondo
Airline
Rating
Free Cancellation
Price
VivaPriceFrom $261Free CancellationRating
7.0
816 reviews
Search Viva flights
VolarisPriceFrom $272Free CancellationRating
6.6
1,175 reviews
Search Volaris flights
United AirlinesPriceFrom $453Free CancellationRating
7.4
9,219 reviews
Search United Airlines flights
AeromexicoPriceFrom $455Free CancellationRating
7.4
1,583 reviews
Search Aeromexico flights
DeltaPriceFrom $484Free CancellationRating
7.9
8,130 reviews
Search Delta flights
American AirlinesPriceFrom $505Free CancellationRating
7.2
11,211 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Oaxaca?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Oaxaca for you.

Can I find flights from Chicago to Oaxaca with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Oaxaca from Chicago with this policy.

How can momondo help me find flights from Chicago to Oaxaca?

momondo helps you find the best flight between Chicago and Oaxaca by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Oaxaca right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Oaxaca, momondo offers a useful price alert feature which will track prices for flights to Oaxaca from Chicago and alert you when they change.

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