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Cheap flights from Chicago to Oaxaca from $123

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 5/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
Volaris Logo
1:49 pm - 9:09 pm
ORD
-
OAX
8h 20m
1 stop
Volaris Logo
2:29 pm - 12:55 am
OAX
-
ORD
9h 26m
1 stop
$310Volaris
Tue, Jul 7 - Tue, Jul 14
Volaris Logo
1:40 am - 8:13 am
ORD
-
OAX
7h 33m
1 stop
Volaris Logo
8:23 pm - 4:41 am
OAX
-
ORD
7h 18m
1 stop
$311Volaris
Tue, May 26 - Mon, Jun 1
Viva Logo
1:30 am - 3:00 pm
ORD
-
OAX
14h 30m
1 stop
Viva Logo
3:30 pm - 11:55 pm
OAX
-
ORD
7h 25m
1 stop
$317Viva
Mon, Jun 1 - Thu, Jun 18
Multiple Airlines Logo
1:40 am - 8:13 am
ORD
-
OAX
7h 33m
1 stop
Multiple Airlines Logo
3:30 pm - 11:55 pm
OAX
-
ORD
7h 25m
1 stop
$319Multiple Airlines
Tue, May 26 - Mon, Jun 1
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
$321Volaris
Sun, May 17 - Fri, May 22
Multiple Airlines Logo
1:40 am - 8:13 am
ORD
-
OAX
7h 33m
1 stop
Multiple Airlines Logo
3:30 pm - 12:45 am
OAX
-
ORD
8h 15m
1 stop
$322Multiple Airlines
Sat, May 16 - Fri, May 22
Multiple Airlines Logo
1:40 am - 8:13 am
ORD
-
OAX
7h 33m
1 stop
Multiple Airlines Logo
3:37 pm - 11:45 pm
OAX
-
ORD
7h 08m
1 stop
$323Multiple Airlines
Sat, Sep 12 - Sun, Sep 27
Volaris Logo
1:40 am - 8:13 am
ORD
-
OAX
7h 33m
1 stop
Volaris Logo
2:29 pm - 12:55 am
OAX
-
ORD
9h 26m
1 stop
$329Volaris
Tue, May 26 - Tue, Jun 2
Delta Logo
10:35 am - 10:43 pm
MDW
-
OAX
13h 08m
2 stops
Delta Logo
6:05 am - 9:45 pm
OAX
-
MDW
14h 40m
2 stops
$575Delta
Tue, Sep 29 - Tue, Oct 6
Delta Logo
1:05 pm - 10:43 pm
MDW
-
OAX
10h 38m
2 stops
Delta Logo
8:40 am - 9:46 pm
OAX
-
MDW
12h 06m
2 stops
$605Delta
Wed, Sep 2 - Sat, Sep 12

Volaris flights from Chicago to Oaxaca

Our best Volaris deals on Chicago to Oaxaca flight tickets
Volaris
Jul 7
ORD1:49 pmChicago O'Hare Intl
8h 20m
1 stop
OAX9:09 pmOaxaca Xoxocotlan
Jul 14
OAX2:29 pmOaxaca Xoxocotlan
9h 26m
1 stop
ORD12:55 amChicago O'Hare Intl
$310
Volaris
May 26
ORD1:40 amChicago O'Hare Intl
7h 33m
1 stop
OAX8:13 amOaxaca Xoxocotlan
Jun 1
OAX8:23 pmOaxaca Xoxocotlan
7h 18m
1 stop
ORD4:41 amChicago O'Hare Intl
$311
Volaris
May 4
ORD1:40 amChicago O'Hare Intl
7h 33m
1 stop
OAX8:13 amOaxaca Xoxocotlan
May 9
OAX7:34 pmOaxaca Xoxocotlan
9h 18m
1 stop
ORD5:52 amChicago O'Hare Intl
$314

Aeromexico flights from Chicago to Oaxaca

Our best Aeromexico deals on Chicago to Oaxaca flight tickets
Aeromexico
May 10
ORD1:45 pmChicago O'Hare Intl
19h 20m
2 stops
OAX8:05 amOaxaca Xoxocotlan
May 18
OAX6:27 pmOaxaca Xoxocotlan
23h 14m
2 stops
ORD6:41 pmChicago O'Hare Intl
$686
Aeromexico
May 9
ORD9:10 amChicago O'Hare Intl
24h 24m
2 stops
OAX8:34 amOaxaca Xoxocotlan
May 11
OAX12:46 pmOaxaca Xoxocotlan
10h 13m
2 stops
ORD11:59 pmChicago O'Hare Intl
$691
Aeromexico
May 9
ORD6:06 pmChicago O'Hare Intl
20h 45m
2 stops
OAX1:51 pmOaxaca Xoxocotlan
May 11
OAX12:46 pmOaxaca Xoxocotlan
10h 13m
2 stops
ORD11:59 pmChicago O'Hare Intl
$711

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 May 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

Cheapest round-trip

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 7/7

1:49 pm-9:09 pm

1 stop8h 20m

Oaxaca Xoxocotlan

Tue 7/14

2:29 pm-12:55 am

1 stop9h 26m

$310

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 5/26

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Mon 6/1

8:23 pm-4:41 am

1 stop7h 18m

$311

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Mon 6/1

1:30 am-3:00 pm

1 stop14h 30m

Oaxaca Xoxocotlan

Thu 6/18

3:30 pm-11:55 pm

1 stop7h 25m

$317

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 5/26

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Mon 6/1

3:30 pm-11:55 pm

1 stop7h 25m

$319

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 5/17

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Fri 5/22

7:34 pm-5:52 am

1 stop9h 18m

$321

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 5/16

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Fri 5/22

3:30 pm-12:45 am

1 stop8h 15m

$322
Quickest round-trip

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 9/12

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Sun 9/27

3:37 pm-11:45 pm

1 stop7h 08m

$323

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 5/26

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Tue 6/2

2:29 pm-12:55 am

1 stop9h 26m

$329

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Tue 9/29

10:35 am-10:43 pm

2 stops13h 08m

Oaxaca Xoxocotlan

Tue 10/6

6:05 am-9:45 pm

2 stops14h 40m

$575

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 9/2

1:05 pm-10:43 pm

2 stops10h 38m

Oaxaca Xoxocotlan

Sat 9/12

8:40 am-9:46 pm

2 stops12h 06m

$605

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, March 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 $182. If you are unable to visit Oaxaca during the month of March, then departing from Chicago during the month December is also very affordable. Most momondo users find prices during this month for around $189.

How far in advance should I book a flight from Chicago 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 $525 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 $373 on momondo.

How have Chicago to Oaxaca flight prices changed over time?

As of May 2026, prices for Chicago to Oaxaca flights are approximately 57% 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 38m

Direct flights

None
The fastest flight from Chicago to Oaxaca takes 7h 38m
There are no direct flights from Chicago to Oaxaca. There are no popular flight routes from Chicago to Oaxaca.
Search flight deals

Frequently asked questions about flying from Chicago to Oaxaca

  • 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 38m.

  • 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
809 reviews
Search Viva flights
VolarisPriceFrom $277Free CancellationRating
6.6
1,166 reviews
Search Volaris flights
AeromexicoPriceFrom $455Free CancellationRating
7.4
1,520 reviews
Search Aeromexico flights
DeltaPriceFrom $475Free CancellationRating
7.9
8,464 reviews
Search Delta flights
United AirlinesPriceFrom $520Free CancellationRating
7.4
9,677 reviews
Search United Airlines flights
American AirlinesPriceFrom $543Free CancellationRating
7.1
11,684 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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