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Cheap flights from Santo Domingo to Chicago from $166

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 4/8. 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 Santo Domingo to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
4:08 pm - 8:07 pm
SDQ
-
MDW
28h 59m
1 stop
Frontier Logo
6:30 am - 1:56 pm
MDW
-
SDQ
6h 26m
1 stop
$289Frontier
Wed, Apr 8 - Sat, Apr 11
Frontier Logo
4:08 pm - 8:07 pm
SDQ
-
MDW
28h 59m
1 stop
Frontier Logo
5:05 am - 10:07 am
MDW
-
SDQ
28h 02m
1 stop
$290Frontier
Wed, Apr 8 - Sun, Apr 12
Multiple Airlines Logo
10:19 am - 10:26 pm
SDQ
-
MDW
13h 07m
2 stops
Multiple Airlines Logo
7:30 am - 4:30 pm
MDW
-
SDQ
8h 00m
1 stop
$455Multiple Airlines
Fri, Apr 24 - Fri, May 1
Multiple Airlines Logo
7:10 pm - 1:00 pm
SDQ
-
MDW
18h 50m
1 stop
Multiple Airlines Logo
7:30 am - 4:30 pm
MDW
-
SDQ
8h 00m
1 stop
$458Multiple Airlines
Fri, Apr 24 - Fri, May 1
Multiple Airlines Logo
10:19 am - 10:19 pm
SDQ
-
MDW
13h 00m
2 stops
Multiple Airlines Logo
7:30 am - 4:30 pm
MDW
-
SDQ
8h 00m
1 stop
$470Multiple Airlines
Mon, Apr 20 - Mon, Apr 27
Multiple Airlines Logo
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
12:27 pm - 5:29 am
MDW
-
SDQ
16h 02m
2 stops
$521Multiple Airlines
Fri, Apr 24 - Tue, May 5
Multiple Airlines Logo
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
2:15 pm - 1:29 pm
MDW
-
SDQ
22h 14m
2 stops
$525Multiple Airlines
Mon, Apr 27 - Sun, May 3
Delta Logo
2:49 pm - 9:09 pm
SDQ
-
MDW
7h 20m
1 stop
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
$560Delta
Mon, May 11 - Wed, Sep 9
Multiple Airlines Logo
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
2:15 pm - 1:29 pm
MDW
-
SDQ
22h 14m
2 stops
$571Multiple Airlines
Fri, May 1 - Sun, May 3
Delta Logo
2:37 pm - 10:28 pm
SDQ
-
MDW
8h 51m
1 stop
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
$573Delta
Sat, Apr 25 - Sun, May 3

Frontier flights from Santo Domingo to Chicago Midway Airport

Our best Frontier deals on Santo Domingo to Chicago Midway Airport flight tickets
Frontier
Apr 8
SDQ4:08 pmSanto Domingo Las Americas
28h 59m
1 stop
MDW8:07 pmChicago Midway
Apr 11
MDW6:30 amChicago Midway
6h 26m
1 stop
SDQ1:56 pmSanto Domingo Las Americas
$289
Frontier
Apr 8
SDQ4:08 pmSanto Domingo Las Americas
28h 59m
1 stop
MDW8:07 pmChicago Midway
Apr 12
MDW5:05 amChicago Midway
28h 02m
1 stop
SDQ10:07 amSanto Domingo Las Americas
$290
Frontier
Mar 30
SDQ10:46 amSanto Domingo Las Americas
29h 47m
1 stop
MDW3:33 pmChicago Midway
Apr 4
MDW6:30 amChicago Midway
6h 26m
1 stop
SDQ1:56 pmSanto Domingo Las Americas
$473

Delta flights from Santo Domingo to Chicago Midway Airport

Our best Delta deals on Santo Domingo to Chicago Midway Airport flight tickets
Delta
May 11
SDQ2:49 pmSanto Domingo Las Americas
7h 20m
1 stop
MDW9:09 pmChicago Midway
Sep 9
MDW6:00 amChicago Midway
6h 12m
1 stop
SDQ1:12 pmSanto Domingo Las Americas
$560
Delta
Apr 25
SDQ2:37 pmSanto Domingo Las Americas
8h 51m
1 stop
MDW10:28 pmChicago Midway
May 3
MDW6:00 amChicago Midway
6h 12m
1 stop
SDQ1:12 pmSanto Domingo Las Americas
$573
Delta
Apr 24
SDQ6:05 amSanto Domingo Las Americas
12h 53m
2 stops
MDW5:58 pmChicago Midway
May 5
MDW6:00 amChicago Midway
11h 34m
2 stops
SDQ6:34 pmSanto Domingo Las Americas
$580

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 March 24, 2026.
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

Cheapest round-trip

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 4/8

4:08 pm-8:07 pm

1 stop28h 59m

Chicago Midway

Sat 4/11

6:30 am-1:56 pm

1 stop6h 26m

$289

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 4/8

4:08 pm-8:07 pm

1 stop28h 59m

Chicago Midway

Sun 4/12

5:05 am-10:07 am

1 stop28h 02m

$290

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 4/24

10:19 am-10:26 pm

2 stops13h 07m

Chicago Midway

Fri 5/1

7:30 am-4:30 pm

1 stop8h 00m

$455

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 4/24

7:10 pm-1:00 pm

1 stop18h 50m

Chicago Midway

Fri 5/1

7:30 am-4:30 pm

1 stop8h 00m

$458

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 4/20

10:19 am-10:19 pm

2 stops13h 00m

Chicago Midway

Mon 4/27

7:30 am-4:30 pm

1 stop8h 00m

$470

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 4/24

6:10 am-1:00 pm

1 stop7h 50m

Chicago Midway

Tue 5/5

12:27 pm-5:29 am

2 stops16h 02m

$521

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 4/27

6:10 am-1:00 pm

1 stop7h 50m

Chicago Midway

Sun 5/3

2:15 pm-1:29 pm

2 stops22h 14m

$525
Quickest round-trip

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 5/11

2:49 pm-9:09 pm

1 stop7h 20m

Chicago Midway

Wed 9/9

6:00 am-1:12 pm

1 stop6h 12m

$560

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Fri 5/1

6:10 am-1:00 pm

1 stop7h 50m

Chicago Midway

Sun 5/3

2:15 pm-1:29 pm

2 stops22h 14m

$571

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 4/25

2:37 pm-10:28 pm

1 stop8h 51m

Chicago Midway

Sun 5/3

6:00 am-1:12 pm

1 stop6h 12m

$573

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 44% 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

Fastest flight time

7h 20m

Direct flights

None
The fastest flight from Santo Domingo to Chicago Midway Airport takes 7h 20m
There are no direct flights from Santo Domingo to Chicago Midway Airport. There are no popular flight routes from Santo Domingo to 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 20m.

  • 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
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Benton Harbor
Portage
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Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
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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