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Cheap flights from Chicago to Oaxaca from $106

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
1:40 am - 8:13 am
ORD
-
OAX
7h 33m
1 stop
Volaris Logo
7:34 pm - 5:52 am
OAX
-
ORD
9h 18m
1 stop
$248Volaris
Sat, May 16 - Sat, May 23
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
$260Volaris
Sat, May 9 - Mon, May 18
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
$265Volaris
Sat, May 9 - Mon, May 18
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
$267Volaris
Mon, Apr 13 - Tue, Apr 21
Frontier Logo
2:15 pm - 1:57 pm
MDW
-
OAX
48h 42m
2 stops
Frontier Logo
9:00 am - 2:12 pm
OAX
-
MDW
52h 12m
2 stops
$552Frontier
Mon, May 4 - Fri, May 8
Delta Logo
6:00 am - 4:43 pm
MDW
-
OAX
11h 43m
2 stops
Delta Logo
6:05 am - 10:28 pm
OAX
-
MDW
15h 23m
2 stops
$589Delta
Wed, Apr 22 - Wed, Apr 29
Delta Logo
6:23 am - 7:22 pm
MDW
-
OAX
13h 59m
2 stops
Delta Logo
10:31 am - 8:42 am
OAX
-
MDW
21h 11m
2 stops
$609Delta
Tue, May 19 - Thu, May 28
Delta Logo
6:00 am - 7:11 pm
MDW
-
OAX
14h 11m
2 stops
Delta Logo
10:31 am - 10:28 pm
OAX
-
MDW
10h 57m
2 stops
$616Delta
Wed, Apr 29 - Tue, May 5
Frontier Logo
6:00 am - 1:57 pm
MDW
-
OAX
32h 57m
2 stops
Frontier Logo
9:00 am - 2:12 pm
OAX
-
MDW
52h 12m
2 stops
$621Frontier
Sun, May 17 - Sat, May 23
Frontier Logo
2:15 pm - 1:57 pm
MDW
-
OAX
48h 42m
2 stops
Frontier Logo
9:00 am - 2:12 pm
OAX
-
MDW
52h 12m
2 stops
$644Frontier
Thu, Apr 30 - Thu, May 7

Volaris flights from Chicago to Oaxaca

Our best Volaris deals on Chicago to Oaxaca flight tickets
Volaris
May 16
ORD1:40 amChicago O'Hare Intl
7h 33m
1 stop
OAX8:13 amOaxaca Xoxocotlan
May 23
OAX7:34 pmOaxaca Xoxocotlan
9h 18m
1 stop
ORD5:52 amChicago O'Hare Intl
$248
Volaris
May 9
ORD1:40 amChicago O'Hare Intl
7h 33m
1 stop
OAX8:13 amOaxaca Xoxocotlan
May 18
OAX7:34 pmOaxaca Xoxocotlan
9h 18m
1 stop
ORD5:52 amChicago O'Hare Intl
$260
Volaris
May 9
ORD1:40 amChicago O'Hare Intl
7h 33m
1 stop
OAX8:13 amOaxaca Xoxocotlan
May 18
OAX7:34 pmOaxaca Xoxocotlan
9h 18m
1 stop
ORD5:52 amChicago O'Hare Intl
$265

Delta flights from Chicago to Oaxaca

Our best Delta deals on Chicago to Oaxaca flight tickets
Delta
Apr 22
MDW6:00 amChicago Midway
11h 43m
2 stops
OAX4:43 pmOaxaca Xoxocotlan
Apr 29
OAX6:05 amOaxaca Xoxocotlan
15h 23m
2 stops
MDW10:28 pmChicago Midway
$589
Delta
May 19
MDW6:23 amChicago Midway
11h 15m
2 stops
OAX4:38 pmOaxaca Xoxocotlan
May 26
OAX5:42 pmOaxaca Xoxocotlan
21h 30m
2 stops
MDW4:12 pmChicago Midway
$609
Delta
Apr 29
MDW6:00 amChicago Midway
14h 11m
2 stops
OAX7:11 pmOaxaca Xoxocotlan
May 5
OAX10:31 amOaxaca Xoxocotlan
10h 57m
2 stops
MDW10:28 pmChicago Midway
$616

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 March 17, 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
Quickest round-trip

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 5/16

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Sat 5/23

7:34 pm-5:52 am

1 stop9h 18m

$248

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 5/9

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Mon 5/18

7:34 pm-5:52 am

1 stop9h 18m

$260

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Sat 5/9

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Mon 5/18

7:34 pm-5:52 am

1 stop9h 18m

$265

ChicagoOaxaca

ORD - OAX

ORDOAX

Chicago O'Hare Intl

Mon 4/13

1:40 am-8:13 am

1 stop7h 33m

Oaxaca Xoxocotlan

Tue 4/21

7:34 pm-5:52 am

1 stop9h 18m

$267

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Mon 5/4

2:15 pm-1:57 pm

2 stops48h 42m

Oaxaca Xoxocotlan

Fri 5/8

9:00 am-2:12 pm

2 stops52h 12m

$552

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 4/22

6:00 am-4:43 pm

2 stops11h 43m

Oaxaca Xoxocotlan

Wed 4/29

6:05 am-10:28 pm

2 stops15h 23m

$589

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Tue 5/19

6:23 am-7:22 pm

2 stops13h 59m

Oaxaca Xoxocotlan

Thu 5/28

10:31 am-8:42 am

2 stops21h 11m

$609

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Wed 4/29

6:00 am-7:11 pm

2 stops14h 11m

Oaxaca Xoxocotlan

Tue 5/5

10:31 am-10:28 pm

2 stops10h 57m

$616

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Sun 5/17

6:00 am-1:57 pm

2 stops32h 57m

Oaxaca Xoxocotlan

Sat 5/23

9:00 am-2:12 pm

2 stops52h 12m

$621

ChicagoOaxaca

MDW - OAX

MDWOAX

Chicago Midway

Thu 4/30

2:15 pm-1:57 pm

2 stops48h 42m

Oaxaca Xoxocotlan

Thu 5/7

9:00 am-2:12 pm

2 stops52h 12m

$644

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 $369. 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 $408.

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 $538 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 $375 on momondo.

How have Chicago to Oaxaca flight prices changed over time?

As of March 2026, prices for Chicago to Oaxaca flights are approximately 71% 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 12m

Direct flights

None
The fastest flight from Chicago to Oaxaca takes 7h 12m
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 12m.

  • 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
819 reviews
Search Viva flights
VolarisPriceFrom $277Free CancellationRating
6.6
1,170 reviews
Search Volaris flights
United AirlinesPriceFrom $453Free CancellationRating
7.4
9,431 reviews
Search United Airlines flights
AeromexicoPriceFrom $455Free CancellationRating
7.4
1,564 reviews
Search Aeromexico flights
DeltaPriceFrom $475Free CancellationRating
7.9
8,288 reviews
Search Delta flights
American AirlinesPriceFrom $505Free CancellationRating
7.1
11,468 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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