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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 1/15. 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.
Multiple Airlines Logo
1:40 am - 8:13 amORD-OAX
7h 33m1 stop
Multiple Airlines Logo
3:30 pm - 12:45 amOAX-ORD
8h 15m1 stop
$253Multiple Airlines
Find Deal
Wed, Apr 22 - Sun, Apr 26
Multiple Airlines Logo
12:58 am - 8:08 amORD-OAX
8h 10m1 stop
Multiple Airlines Logo
3:30 pm - 12:45 amOAX-ORD
8h 15m1 stop
$261Multiple Airlines
Find Deal
Wed, Apr 22 - Wed, Apr 29
Volaris Logo
12:58 am - 8:08 amORD-OAX
8h 10m1 stop
Volaris Logo
8:52 am - 11:07 pmOAX-ORD
13h 15m1 stop
$279Volaris
Find Deal
Wed, Apr 22 - Wed, Apr 29
Viva Logo
1:00 am - 12:25 pmORD-OAX
11h 25m1 stop
Viva Logo
4:55 pm - 11:50 pmOAX-ORD
6h 55m1 stop
$295Viva
Find Deal
Sat, Jan 17 - Mon, Feb 9
Viva Logo
1:00 am - 12:25 pmORD-OAX
11h 25m1 stop
Viva Logo
1:10 pm - 11:25 pmOAX-ORD
10h 15m1 stop
$298Viva
Find Deal
Tue, Jan 20 - Wed, Jan 28
Volaris Logo
11:58 pm - 7:19 amORD-OAX
7h 21m1 stop
Volaris Logo
8:56 am - 10:06 pmOAX-ORD
13h 10m1 stop
$303Volaris
Find Deal
Sun, Feb 8 - Sun, Feb 15
Aeromexico Logo
6:45 am - 9:40 amMDW-OAX
26h 55m2 stops
Aeromexico Logo
8:14 pm - 10:09 pmOAX-MDW
25h 55m2 stops
$644Aeromexico
Find Deal
Fri, Jan 9 - Wed, Jan 14
Delta Logo
6:00 am - 7:13 pmMDW-OAX
14h 13m2 stops
Delta Logo
6:05 am - 9:45 pmOAX-MDW
14h 40m2 stops
$684Delta
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Sat, Apr 18 - Sun, Apr 26
Delta Logo
6:00 am - 6:47 pmMDW-OAX
12h 47m2 stops
Delta Logo
10:23 am - 11:47 pmOAX-MDW
13h 24m2 stops
$727Delta
Find Deal
Sat, Dec 6 - Fri, Dec 12
Aeromexico Logo
6:45 am - 9:40 amMDW-OAX
26h 55m2 stops
Aeromexico Logo
8:14 pm - 10:09 pmOAX-MDW
25h 55m2 stops
$748Aeromexico
Find Deal
Fri, Jan 9 - Wed, Jan 14

Viva flights from Chicago to Oaxaca

Our best Viva deals on Chicago to Oaxaca flight tickets
Viva
Jan 17
ORD1:00 amChicago O'Hare Intl
11h 25m
1 stop
OAX12:25 pmOaxaca Xoxocotlan
Feb 9
OAX4:55 pmOaxaca Xoxocotlan
6h 55m
1 stop
ORD11:50 pmChicago O'Hare Intl
$295
Find similar
Viva
Jan 20
ORD1:00 amChicago O'Hare Intl
11h 25m
1 stop
OAX12:25 pmOaxaca Xoxocotlan
Jan 28
OAX1:10 pmOaxaca Xoxocotlan
10h 15m
1 stop
ORD11:25 pmChicago O'Hare Intl
$298
Find similar
Viva
Jan 28
ORD1:20 amChicago O'Hare Intl
15h 05m
1 stop
OAX4:25 pmOaxaca Xoxocotlan
Feb 10
OAX1:10 pmOaxaca Xoxocotlan
10h 15m
1 stop
ORD11:25 pmChicago O'Hare Intl
$311
Find similar

Aeromexico flights from Chicago to Oaxaca

Our best Aeromexico deals on Chicago to Oaxaca flight tickets
Aeromexico
Nov 8
ORD6:10 pmChicago O'Hare Intl
22h 01m
2 stops
OAX4:11 pmOaxaca Xoxocotlan
Nov 10
OAX8:19 pmOaxaca Xoxocotlan
20h 27m
2 stops
ORD4:46 pmChicago O'Hare Intl
$439
Find similar
Aeromexico
Nov 7
ORD5:51 pmChicago O'Hare Intl
21h 07m
2 stops
OAX2:58 pmOaxaca Xoxocotlan
Nov 12
OAX8:09 pmOaxaca Xoxocotlan
17h 03m
1 stop
ORD1:12 pmChicago O'Hare Intl
$463
Find similar
Aeromexico
Nov 7
ORD5:51 pmChicago O'Hare Intl
21h 07m
2 stops
OAX2:58 pmOaxaca Xoxocotlan
Nov 15
OAX8:27 amOaxaca Xoxocotlan
14h 14m
1 stop
ORD10:41 pmChicago O'Hare Intl
$467
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 October 30, 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

Wed 4/22

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Sun 4/26

3:30 pm-12:45 am

1 stop8h 15m

$253

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 4/22

12:58 am-8:08 am

1 stop8h 10m

Oaxaca Xoxocotlan

Wed 4/29

3:30 pm-12:45 am

1 stop8h 15m

$261

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Wed 4/22

12:58 am-8:08 am

1 stop8h 10m

Oaxaca Xoxocotlan

Wed 4/29

8:52 am-11:07 pm

1 stop13h 15m

$279

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 1/17

1:00 am-12:25 pm

1 stop11h 25m

Oaxaca Xoxocotlan

Mon 2/9

4:55 pm-11:50 pm

1 stop6h 55m

$295

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Tue 1/20

1:00 am-12:25 pm

1 stop11h 25m

Oaxaca Xoxocotlan

Wed 1/28

1:10 pm-11:25 pm

1 stop10h 15m

$298

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sun 2/8

11:58 pm-7:19 am

1 stop7h 21m

Oaxaca Xoxocotlan

Sun 2/15

8:56 am-10:06 pm

1 stop13h 10m

$303

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Fri 1/9

6:45 am-9:40 am

2 stops26h 55m

Oaxaca Xoxocotlan

Wed 1/14

8:14 pm-10:09 pm

2 stops25h 55m

$644

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sat 4/18

6:00 am-7:13 pm

2 stops14h 13m

Oaxaca Xoxocotlan

Sun 4/26

6:05 am-9:45 pm

2 stops14h 40m

$684

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sat 12/6

6:00 am-6:47 pm

2 stops12h 47m

Oaxaca Xoxocotlan

Fri 12/12

10:23 am-11:47 pm

2 stops13h 24m

$727

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Fri 1/9

6:45 am-9:40 am

2 stops26h 55m

Oaxaca Xoxocotlan

Wed 1/14

8:14 pm-10:09 pm

2 stops25h 55m

$748

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 $523 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 $387 on momondo.

How have Chicago to Oaxaca flight prices changed over time?

As of October 2025, prices for Chicago to Oaxaca flights are approximately 2% 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

Direct flights

None
There are no direct flights from Chicago to Oaxaca. There are no popular flight routes from Chicago to Oaxaca.
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  • 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 $247Free CancellationRating
7.0
790 reviews
Search Viva flights
VolarisPriceFrom $271Free CancellationRating
6.7
1,151 reviews
Search Volaris flights
United AirlinesPriceFrom $453Free CancellationRating
7.4
8,998 reviews
Search United Airlines flights
AeromexicoPriceFrom $455Free CancellationRating
7.4
1,674 reviews
Search Aeromexico flights
DeltaPriceFrom $465Free CancellationRating
7.9
7,997 reviews
Search Delta flights
American AirlinesPriceFrom $531Free CancellationRating
7.2
11,035 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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