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Cheap flights from Chicago to Oaxaca from $103

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 2/25. 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 05m1 stop
Viva Logo
4:55 pm - 11:50 pm
OAX
-
ORD
6h 55m1 stop
$238Viva
Sun, Feb 15 - Mon, Feb 23
Viva Logo
1:20 am - 4:25 pm
ORD
-
OAX
15h 05m1 stop
Viva Logo
4:55 pm - 11:50 pm
OAX
-
ORD
6h 55m1 stop
$239Viva
Sun, Feb 15 - Mon, Feb 23
Viva Logo
1:20 am - 4:25 pm
ORD
-
OAX
15h 05m1 stop
Viva Logo
4:55 pm - 11:50 pm
OAX
-
ORD
6h 55m1 stop
$258Viva
Mon, Jan 12 - Mon, Jan 26
Multiple Airlines Logo
7:11 am - 4:12 pm
ORD
-
OAX
9h 01m1 stop
Multiple Airlines Logo
4:55 pm - 11:50 pm
OAX
-
ORD
6h 55m1 stop
$269Multiple Airlines
Sun, Feb 1 - Fri, Feb 6
Multiple Airlines Logo
11:59 pm - 8:35 am
ORD
-
OAX
8h 36m1 stop
Multiple Airlines Logo
3:25 pm - 11:50 pm
OAX
-
ORD
8h 25m1 stop
$274Multiple Airlines
Sat, Feb 7 - Sun, Feb 15
Volaris Logo
1:40 am - 8:13 am
ORD
-
OAX
7h 33m1 stop
Volaris Logo
7:34 pm - 5:57 am
OAX
-
ORD
9h 23m1 stop
$275Volaris
Sat, May 9 - Sun, May 17
Aeromexico Logo
6:00 am - 10:40 pm
MDW
-
OAX
16h 40m2 stops
Aeromexico Logo
8:25 pm - 5:29 pm
OAX
-
MDW
21h 04m2 stops
$451Aeromexico
Mon, Feb 2 - Mon, Feb 9
Delta Logo
6:00 am - 7:03 pm
MDW
-
OAX
13h 03m2 stops
Delta Logo
8:01 am - 10:22 pm
OAX
-
MDW
14h 21m2 stops
$471Delta
Mon, Feb 2 - Sat, Feb 7
Delta Logo
6:00 am - 7:03 pm
MDW
-
OAX
13h 03m2 stops
Delta Logo
6:01 am - 5:29 pm
OAX
-
MDW
11h 28m2 stops
$473Delta
Wed, Jan 28 - Wed, Feb 4
Aeromexico Logo
6:00 am - 7:00 pm
MDW
-
OAX
13h 00m2 stops
Aeromexico Logo
8:25 pm - 10:44 pm
OAX
-
MDW
26h 19m2 stops
$489Aeromexico
Mon, Feb 16 - Mon, Feb 23

Viva flights from Chicago to Oaxaca

Our best Viva deals on Chicago to Oaxaca flight tickets
Viva
Feb 15
ORD1:20 amChicago O'Hare Intl
15h 05m
1 stop
OAX4:25 pmOaxaca Xoxocotlan
Feb 23
OAX4:55 pmOaxaca Xoxocotlan
6h 55m
1 stop
ORD11:50 pmChicago O'Hare Intl
$238
Find similar
Viva
Feb 15
ORD1:20 amChicago O'Hare Intl
15h 05m
1 stop
OAX4:25 pmOaxaca Xoxocotlan
Feb 23
OAX4:55 pmOaxaca Xoxocotlan
6h 55m
1 stop
ORD11:50 pmChicago O'Hare Intl
$239
Find similar
Viva
Feb 15
ORD1:20 amChicago O'Hare Intl
15h 05m
1 stop
OAX4:25 pmOaxaca Xoxocotlan
Feb 20
OAX4:55 pmOaxaca Xoxocotlan
6h 55m
1 stop
ORD11:50 pmChicago O'Hare Intl
$266
Find similar

Aeromexico flights from Chicago to Oaxaca

Our best Aeromexico deals on Chicago to Oaxaca flight tickets
Aeromexico
Feb 2
MDW6:00 amChicago Midway
16h 40m
2 stops
OAX10:40 pmOaxaca Xoxocotlan
Feb 9
OAX8:25 pmOaxaca Xoxocotlan
21h 04m
2 stops
MDW5:29 pmChicago Midway
$451
Find similar
Aeromexico
Feb 16
MDW6:00 amChicago Midway
13h 00m
2 stops
OAX7:00 pmOaxaca Xoxocotlan
Feb 23
OAX8:25 pmOaxaca Xoxocotlan
26h 19m
2 stops
MDW10:44 pmChicago Midway
$489
Find similar
Aeromexico
Apr 18
MDW6:00 amChicago Midway
14h 13m
2 stops
OAX7:13 pmOaxaca Xoxocotlan
Apr 26
OAX9:30 pmOaxaca Xoxocotlan
23h 15m
2 stops
MDW9:45 pmChicago Midway
$533
Find similar

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 December 16, 2025.
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

Sun 2/15

1:20 am-4:25 pm

1 stop15h 05m

Oaxaca Xoxocotlan

Mon 2/23

4:55 pm-11:50 pm

1 stop6h 55m

$238

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 2/15

1:20 am-4:25 pm

1 stop15h 05m

Oaxaca Xoxocotlan

Mon 2/23

4:55 pm-11:50 pm

1 stop6h 55m

$239

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Mon 1/12

1:20 am-4:25 pm

1 stop15h 05m

Oaxaca Xoxocotlan

Mon 1/26

4:55 pm-11:50 pm

1 stop6h 55m

$258

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 2/1

7:11 am-4:12 pm

1 stop9h 01m

Oaxaca Xoxocotlan

Fri 2/6

4:55 pm-11:50 pm

1 stop6h 55m

$269

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 2/7

11:59 pm-8:35 am

1 stop8h 36m

Oaxaca Xoxocotlan

Sun 2/15

3:25 pm-11:50 pm

1 stop8h 25m

$274

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 5/9

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Sun 5/17

7:34 pm-5:57 am

1 stop9h 23m

$275

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 2/2

6:00 am-10:40 pm

2 stops16h 40m

Oaxaca Xoxocotlan

Mon 2/9

8:25 pm-5:29 pm

2 stops21h 04m

$451

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 2/2

6:00 am-7:03 pm

2 stops13h 03m

Oaxaca Xoxocotlan

Sat 2/7

8:01 am-10:22 pm

2 stops14h 21m

$471

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 1/28

6:00 am-7:03 pm

2 stops13h 03m

Oaxaca Xoxocotlan

Wed 2/4

6:01 am-5:29 pm

2 stops11h 28m

$473

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 2/16

6:00 am-7:00 pm

2 stops13h 00m

Oaxaca Xoxocotlan

Mon 2/23

8:25 pm-10:44 pm

2 stops26h 19m

$489

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 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.

What is the cheapest day to depart on your flight to Oaxaca?

The cheapest day to depart from Chicago to Oaxaca is on a Monday when prices can be found for as low as $515. The most expensive day to fly to Oaxaca is Saturday, with ticket prices averaging around $594.

What is the cheapest time of day to depart on your flight to Oaxaca?

Our data shows that the cheapest Chicago to Oaxaca flights are usually those with departure times in the afternoon. Our users have found flights to Oaxaca in the afternoon for as low as $500. Try not to purchase tickets in the morning because they tend to be around $656. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 $537 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 $369 on momondo.

How have Chicago to Oaxaca flight prices changed over time?

As of December 2025, prices for Chicago to Oaxaca flights are approximately 35% 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 23m

Direct flights

None
The fastest flight from Chicago to Oaxaca takes 7h 23m
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 23m.

  • 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 $247Free CancellationRating
7.0
796 reviews
Search Viva flights
VolarisPriceFrom $271Free CancellationRating
6.7
1,153 reviews
Search Volaris flights
AeromexicoPriceFrom $455Free CancellationRating
7.4
1,630 reviews
Search Aeromexico flights
DeltaPriceFrom $465Free CancellationRating
7.9
8,009 reviews
Search Delta flights
United AirlinesPriceFrom $520Free CancellationRating
7.4
9,094 reviews
Search United Airlines flights
American AirlinesPriceFrom $543Free CancellationRating
7.2
11,047 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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