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Cheap flights from Santo Domingo to Chicago from $233

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Santo Domingo to Chicago departing on 10/9. 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 Santo Domingo to Chicago

Cheap round-trip flights

Frontier Logo
3:11 pm - 6:18 pmSDQ-MDW
28h 07m1 stop
Frontier Logo
8:00 am - 1:51 pmMDW-SDQ
28h 51m1 stop
$440Frontier
Find Deal
Thu, Oct 16 - Wed, Oct 22
Delta Logo
2:56 pm - 10:14 pmSDQ-MDW
8h 18m1 stop
Delta Logo
6:00 am - 1:41 pmMDW-SDQ
6h 41m1 stop
$450Delta
Find Deal
Mon, Oct 27 - Thu, Oct 30
Frontier Logo
3:11 pm - 11:25 pmSDQ-MDW
9h 14m1 stop
Frontier Logo
6:15 am - 5:20 pmMDW-SDQ
10h 05m2 stops
$498Frontier
Find Deal
Thu, Oct 9 - Mon, Oct 13
Frontier Logo
3:11 pm - 11:25 pmSDQ-MDW
9h 14m1 stop
Frontier Logo
6:15 am - 5:20 pmMDW-SDQ
10h 05m2 stops
$510Frontier
Find Deal
Thu, Oct 9 - Mon, Oct 13
Frontier Logo
6:29 pm - 9:51 amSDQ-MDW
16h 22m2 stops
Frontier Logo
6:21 am - 5:24 pmMDW-SDQ
10h 03m2 stops
$546Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 8
Delta Logo
2:56 pm - 10:14 pmSDQ-MDW
8h 18m1 stop
Delta Logo
6:00 am - 1:41 pmMDW-SDQ
6h 41m1 stop
$551Delta
Find Deal
Thu, Oct 9 - Tue, Oct 14
Frontier Logo
6:29 pm - 7:11 amSDQ-MDW
37h 42m2 stops
Frontier Logo
6:21 am - 5:24 pmMDW-SDQ
10h 03m2 stops
$595Frontier
Find Deal
Fri, Sep 12 - Mon, Sep 15
Frontier Logo
6:29 pm - 11:17 pmSDQ-MDW
29h 48m2 stops
Frontier Logo
6:21 am - 5:24 pmMDW-SDQ
10h 03m2 stops
$607Frontier
Find Deal
Fri, Sep 12 - Mon, Sep 15
Delta Logo
2:56 pm - 10:14 pmSDQ-MDW
8h 18m1 stop
Delta Logo
6:00 am - 1:41 pmMDW-SDQ
6h 41m1 stop
$623Delta
Find Deal
Thu, Oct 9 - Tue, Oct 14
Delta Logo
6:00 am - 6:37 pmSDQ-MDW
13h 37m2 stops
Delta Logo
6:04 am - 1:22 pmMDW-SDQ
6h 18m1 stop
$629Delta
Find Deal
Tue, Aug 12 - Fri, Aug 15

Frontier flights from Santo Domingo to Chicago Midway Airport

Our best Frontier deals on Santo Domingo to Chicago Midway Airport flight tickets
Frontier
Aug 5
SDQ1:48 amSanto Domingo Las Americas
9h 52m
1 stop
MDW10:40 amChicago Midway
Aug 12
MDW11:39 amChicago Midway
11h 53m
1 stop
SDQ12:32 amSanto Domingo Las Americas
$380
Find similar
Frontier
Aug 5
SDQ1:48 amSanto Domingo Las Americas
9h 52m
1 stop
MDW10:40 amChicago Midway
Aug 11
MDW6:40 pmChicago Midway
16h 09m
1 stop
SDQ11:49 amSanto Domingo Las Americas
$400
Find similar
Frontier
Oct 16
SDQ3:11 pmSanto Domingo Las Americas
28h 07m
1 stop
MDW6:18 pmChicago Midway
Oct 22
MDW8:00 amChicago Midway
28h 51m
1 stop
SDQ1:51 pmSanto Domingo Las Americas
$440
Find similar

Delta flights from Santo Domingo to Chicago Midway Airport

Our best Delta deals on Santo Domingo to Chicago Midway Airport flight tickets
Delta
Oct 27
SDQ2:56 pmSanto Domingo Las Americas
8h 18m
1 stop
MDW10:14 pmChicago Midway
Oct 30
MDW6:00 amChicago Midway
6h 41m
1 stop
SDQ1:41 pmSanto Domingo Las Americas
$450
Find similar
Delta
Oct 9
SDQ2:56 pmSanto Domingo Las Americas
8h 18m
1 stop
MDW10:14 pmChicago Midway
Oct 14
MDW6:00 amChicago Midway
6h 41m
1 stop
SDQ1:41 pmSanto Domingo Las Americas
$551
Find similar
Delta
Oct 9
SDQ2:56 pmSanto Domingo Las Americas
8h 18m
1 stop
MDW10:14 pmChicago Midway
Oct 14
MDW6:00 amChicago Midway
6h 41m
1 stop
SDQ1:41 pmSanto Domingo Las Americas
$623
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Santo Domingo to Chicago Midway Airport 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 July 31, 2025.
Use the filters below to find and compare flights from Santo Domingo to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/16

3:11 pm-6:18 pm

1 stop28h 07m

Chicago Midway

Wed 10/22

8:00 am-1:51 pm

1 stop28h 51m

$440

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 10/27

2:56 pm-10:14 pm

1 stop8h 18m

Chicago Midway

Thu 10/30

6:00 am-1:41 pm

1 stop6h 41m

$450

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/9

3:11 pm-11:25 pm

1 stop9h 14m

Chicago Midway

Mon 10/13

6:15 am-5:20 pm

2 stops10h 05m

$498

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/9

3:11 pm-11:25 pm

1 stop9h 14m

Chicago Midway

Mon 10/13

6:15 am-5:20 pm

2 stops10h 05m

$510

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 9/5

6:29 pm-9:51 am

2 stops16h 22m

Chicago Midway

Mon 9/8

6:21 am-5:24 pm

2 stops10h 03m

$546

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/9

2:56 pm-10:14 pm

1 stop8h 18m

Chicago Midway

Tue 10/14

6:00 am-1:41 pm

1 stop6h 41m

$551

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 9/12

6:29 pm-7:11 am

2 stops37h 42m

Chicago Midway

Mon 9/15

6:21 am-5:24 pm

2 stops10h 03m

$595

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 9/12

6:29 pm-11:17 pm

2 stops29h 48m

Chicago Midway

Mon 9/15

6:21 am-5:24 pm

2 stops10h 03m

$607

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/9

2:56 pm-10:14 pm

1 stop8h 18m

Chicago Midway

Tue 10/14

6:00 am-1:41 pm

1 stop6h 41m

$623

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 8/12

6:00 am-6:37 pm

2 stops13h 37m

Chicago Midway

Fri 8/15

6:04 am-1:22 pm

1 stop6h 18m

$629

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 Chicago from

How to get the cheapest flight ticket from Santo Domingo to Chicago Midway Airport

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

Can stopping save me money on Santo Domingo to Chicago Midway Airport flights?

You could potentially save up to 8% on your flight if you consider stops on a Santo Domingo to Chicago Midway Airport flight.

When to book flights from Santo Domingo to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Santo Domingo to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Santo Domingo to Chicago Midway Airport (SDQ to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Santo Domingo to Chicago Midway Airport

Best Price Found

$233

Fastest flight time

7h 04m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Santo Domingo in the past 72 hours is $233. The best round-trip flight deal from Santo Domingo to Chicago Midway Airport found on momondo in the last 72 hours is $440.
The fastest flight from Santo Domingo to Chicago Midway Airport takes 7h 04m
There are no direct flights from Santo Domingo to Chicago Midway Airport. Popular non-direct route for this connection is Santo Domingo Las Americas Airport - Chicago Midway Airport.
Search flight deals

  • How far is Santo Domingo Las Americas to Chicago Midway by plane?

    Chicago Midway is 1920.0 mi away from Santo Domingo Las Americas. A reasonable flight in good conditions will take 7h 04m.

  • When did momondo last update prices for flights from Santo Domingo Las Americas Airport to Chicago Midway Airport?

    Prices for flights from Santo Domingo Las Americas Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Santo Domingo Las Americas Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Santo Domingo Las Americas Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
Benton Harbor
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Schererville
Valparaiso
Crown Point
Munster
Chesterton
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Porter
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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Santo Domingo to Chicago?

It is quick and easy to find Santo Domingo to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Santo Domingo to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Santo Domingo to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Santo Domingo to Chicago?

momondo helps you find the best flight between Santo Domingo and Chicago 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 Santo Domingo to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Santo Domingo are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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