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Cheap flights from Chicago to Oaxaca from $108

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 1/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to Oaxaca

Cheap round-trip flights

Viva Logo
4:40 pm - 4:30 pmORD-OAX
23h 50m1 stop
Viva Logo
1:10 pm - 11:30 pmOAX-ORD
10h 20m1 stop
$290Viva
Find Deal
Sat, Nov 15 - Wed, Nov 19
Volaris Logo
11:59 pm - 10:35 amORD-OAX
10h 36m1 stop
Volaris Logo
8:56 am - 11:06 pmOAX-ORD
13h 10m1 stop
$294Volaris
Find Deal
Thu, Mar 5 - Sun, Mar 8
Volaris Logo
1:40 am - 8:08 amORD-OAX
7h 28m1 stop
Volaris Logo
4:36 pm - 12:15 amOAX-ORD
6h 39m1 stop
$311Volaris
Find Deal
Fri, Oct 3 - Wed, Oct 22
Volaris Logo
1:40 am - 8:08 amORD-OAX
7h 28m1 stop
Volaris Logo
4:36 pm - 12:15 amOAX-ORD
6h 39m1 stop
$313Volaris
Find Deal
Fri, Oct 3 - Wed, Oct 22
Volaris Logo
11:59 pm - 10:35 amORD-OAX
10h 36m1 stop
Volaris Logo
8:56 am - 10:06 pmOAX-ORD
13h 10m1 stop
$316Volaris
Find Deal
Thu, Feb 26 - Mon, Mar 2
Viva Logo
12:25 pm - 1:45 pmORD-OAX
26h 20m1 stop
Viva Logo
7:20 pm - 11:35 pmOAX-ORD
27h 15m1 stop
$326Viva
Find Deal
Sat, Oct 11 - Fri, Oct 17
Delta Logo
6:00 am - 4:59 pmMDW-OAX
10h 59m2 stops
Delta Logo
10:25 am - 11:32 pmOAX-MDW
13h 07m2 stops
$504Delta
Find Deal
Wed, Nov 12 - Thu, Nov 20
Delta Logo
6:00 am - 6:16 pmMDW-OAX
13h 16m2 stops
Delta Logo
8:10 am - 9:36 pmOAX-MDW
12h 26m2 stops
$505Delta
Find Deal
Sat, Sep 27 - Tue, Sep 30
Aeromexico Logo
6:00 am - 2:45 pmMDW-OAX
9h 45m2 stops
Aeromexico Logo
6:05 am - 10:14 pmOAX-MDW
15h 09m2 stops
$615Aeromexico
Find Deal
Sun, Oct 12 - Tue, Oct 21
Aeromexico Logo
6:00 am - 10:45 pmMDW-OAX
17h 45m2 stops
Aeromexico Logo
6:10 am - 10:14 pmOAX-MDW
15h 04m2 stops
$645Aeromexico
Find Deal
Fri, Oct 17 - Thu, Oct 23

Viva flights from Chicago to Oaxaca

Our best Viva deals on Chicago to Oaxaca flight tickets
Viva
Nov 15
ORD4:40 pmChicago O'Hare Intl
23h 50m
1 stop
OAX4:30 pmOaxaca Xoxocotlan
Nov 19
OAX1:10 pmOaxaca Xoxocotlan
10h 20m
1 stop
ORD11:30 pmChicago O'Hare Intl
$290
Find similar
Viva
Oct 11
ORD12:25 pmChicago O'Hare Intl
26h 20m
1 stop
OAX1:45 pmOaxaca Xoxocotlan
Oct 17
OAX7:20 pmOaxaca Xoxocotlan
27h 15m
1 stop
ORD11:35 pmChicago O'Hare Intl
$326
Find similar
Viva
Nov 15
ORD4:40 pmChicago O'Hare Intl
23h 50m
1 stop
OAX4:30 pmOaxaca Xoxocotlan
Nov 21
OAX10:25 pmOaxaca Xoxocotlan
16h 45m
1 stop
ORD3:10 pmChicago O'Hare Intl
$328
Find similar

Delta flights from Chicago to Oaxaca

Our best Delta deals on Chicago to Oaxaca flight tickets
Delta
Nov 12
MDW6:00 amChicago Midway
10h 59m
2 stops
OAX4:59 pmOaxaca Xoxocotlan
Nov 20
OAX10:25 amOaxaca Xoxocotlan
13h 07m
2 stops
MDW11:32 pmChicago Midway
$504
Find similar
Delta
Sep 27
MDW6:00 amChicago Midway
13h 16m
2 stops
OAX6:16 pmOaxaca Xoxocotlan
Sep 30
OAX8:10 amOaxaca Xoxocotlan
12h 26m
2 stops
MDW9:36 pmChicago Midway
$505
Find similar
Delta
Nov 15
MDW6:00 amChicago Midway
12h 47m
2 stops
OAX6:47 pmOaxaca Xoxocotlan
Nov 19
OAX11:09 amOaxaca Xoxocotlan
12h 23m
2 stops
MDW11:32 pmChicago Midway
$508
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 September 15, 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

Sat 11/15

4:40 pm-4:30 pm

1 stop23h 50m

Oaxaca Xoxocotlan

Wed 11/19

1:10 pm-11:30 pm

1 stop10h 20m

$290

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Thu 3/5

11:59 pm-10:35 am

1 stop10h 36m

Oaxaca Xoxocotlan

Sun 3/8

8:56 am-11:06 pm

1 stop13h 10m

$294

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Fri 10/3

1:40 am-8:08 am

1 stop7h 28m

Oaxaca Xoxocotlan

Wed 10/22

4:36 pm-12:15 am

1 stop6h 39m

$311

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Fri 10/3

1:40 am-8:08 am

1 stop7h 28m

Oaxaca Xoxocotlan

Wed 10/22

4:36 pm-12:15 am

1 stop6h 39m

$313

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Thu 2/26

11:59 pm-10:35 am

1 stop10h 36m

Oaxaca Xoxocotlan

Mon 3/2

8:56 am-10:06 pm

1 stop13h 10m

$316

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 10/11

12:25 pm-1:45 pm

1 stop26h 20m

Oaxaca Xoxocotlan

Fri 10/17

7:20 pm-11:35 pm

1 stop27h 15m

$326

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 11/12

6:00 am-4:59 pm

2 stops10h 59m

Oaxaca Xoxocotlan

Thu 11/20

10:25 am-11:32 pm

2 stops13h 07m

$504

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sat 9/27

6:00 am-6:16 pm

2 stops13h 16m

Oaxaca Xoxocotlan

Tue 9/30

8:10 am-9:36 pm

2 stops12h 26m

$505

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sun 10/12

6:00 am-2:45 pm

2 stops9h 45m

Oaxaca Xoxocotlan

Tue 10/21

6:05 am-10:14 pm

2 stops15h 09m

$615

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Fri 10/17

6:00 am-10:45 pm

2 stops17h 45m

Oaxaca Xoxocotlan

Thu 10/23

6:10 am-10:14 pm

2 stops15h 04m

$645

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.

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 $529 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 $228 on momondo.

How have Chicago to Oaxaca flight prices changed over time?

As of September 2025, prices for Chicago to Oaxaca flights are approximately 8% more expensive 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 28m.

  • 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 $239Free CancellationRating
7.0
787 reviews
Search Viva flights
VolarisPriceFrom $272Free CancellationRating
6.6
1,154 reviews
Search Volaris flights
AeromexicoPriceFrom $449Free CancellationRating
7.4
1,697 reviews
Search Aeromexico flights
DeltaPriceFrom $465Free CancellationRating
7.9
7,954 reviews
Search Delta flights
American AirlinesPriceFrom $512Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $551Free CancellationRating
7.4
8,929 reviews
Search United 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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