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Cheap flights from the Dominican Republic to Chicago from $172

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the Dominican Republic to Chicago departing on 9/20. 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 the Dominican Republic to Chicago

Recent round-trip flight deals from the Dominican Republic to Chicago

Logo
5:05 pm - 3:58 pmSDQ-MDW
23h 53m2 stops
Logo
8:19 am - 12:15 pmMDW-SDQ
26h 56m1 stop
$417
Find Deal
Wed, Sep 10 - Mon, Sep 15
Delta Logo
6:05 am - 6:25 pmSDQ-MDW
13h 20m2 stops
Delta Logo
6:00 am - 1:41 pmMDW-SDQ
6h 41m1 stop
$450Delta
Find Deal
Mon, Oct 27 - Thu, Oct 30
Delta Logo
2:49 pm - 9:45 amSDQ-MDW
20h 56m2 stops
Delta Logo
1:06 pm - 1:27 amMDW-SDQ
10h 21m2 stops
$452Delta
Find Deal
Wed, Nov 5 - Sat, Nov 8
Delta Logo
3:03 pm - 9:12 pmSDQ-MDW
7h 09m1 stop
Delta Logo
9:35 am - 12:36 amMDW-SDQ
14h 01m2 stops
$456Delta
Find Deal
Sat, Sep 6 - Mon, Sep 15
Logo
6:17 pm - 12:44 pmSDQ-MDW
43h 27m2 stops
Logo
9:48 am - 1:07 pmMDW-SDQ
26h 19m1 stop
$460
Find Deal
Sat, Sep 6 - Fri, Sep 19
Frontier Logo
3:19 pm - 10:03 pmSDQ-MDW
7h 44m1 stop
Frontier Logo
2:06 pm - 2:56 pmMDW-SDQ
22h 50m1 stop
$473Frontier
Find Deal
Thu, Oct 30 - Wed, Nov 5
Frontier Logo
3:14 pm - 8:31 amSDQ-MDW
18h 17m1 stop
Frontier Logo
8:05 am - 2:01 pmMDW-SDQ
28h 56m1 stop
$476Frontier
Find Deal
Thu, Oct 16 - Wed, Oct 22
Frontier Logo
3:19 pm - 10:03 pmSDQ-MDW
7h 44m1 stop
Frontier Logo
2:06 pm - 2:56 pmMDW-SDQ
22h 50m1 stop
$478Frontier
Find Deal
Thu, Oct 30 - Wed, Nov 5
WestJet Logo
12:25 pm - 5:35 pmPUJ-MDW
30h 10m2 stops
WestJet Logo
12:43 pm - 11:29 amMDW-PUJ
21h 46m2 stops
$3,583WestJet
Find Deal
Wed, Sep 10 - Tue, Sep 16
WestJet Logo
9:30 pm - 1:03 pmPUJ-MDW
16h 33m2 stops
WestJet Logo
12:43 pm - 11:29 amMDW-PUJ
21h 46m2 stops
$3,637WestJet
Find Deal
Sat, Sep 13 - Tue, Sep 16

Frontier flights from Dominican Republic to Chicago Midway Airport

Our best Frontier deals on Dominican Republic to Chicago Midway Airport flight tickets
Frontier
Oct 30
SDQ3:19 pmSanto Domingo Las Americas
7h 44m
1 stop
MDW10:03 pmChicago Midway
Nov 5
MDW2:06 pmChicago Midway
22h 50m
1 stop
SDQ2:56 pmSanto Domingo Las Americas
$473
Find similar
Frontier
Oct 16
SDQ3:14 pmSanto Domingo Las Americas
18h 17m
1 stop
MDW8:31 amChicago Midway
Oct 22
MDW8:05 amChicago Midway
28h 56m
1 stop
SDQ2:01 pmSanto Domingo Las Americas
$476
Find similar
Frontier
Oct 30
SDQ3:19 pmSanto Domingo Las Americas
7h 44m
1 stop
MDW10:03 pmChicago Midway
Nov 5
MDW2:06 pmChicago Midway
22h 50m
1 stop
SDQ2:56 pmSanto Domingo Las Americas
$478
Find similar

Delta flights from Dominican Republic to Chicago Midway Airport

Our best Delta deals on Dominican Republic to Chicago Midway Airport flight tickets
Delta
Oct 27
SDQ6:05 amSanto Domingo Las Americas
13h 20m
2 stops
MDW6:25 pmChicago Midway
Oct 30
MDW6:00 amChicago Midway
6h 41m
1 stop
SDQ1:41 pmSanto Domingo Las Americas
$450
Find similar
Delta
Nov 5
SDQ2:49 pmSanto Domingo Las Americas
20h 56m
2 stops
MDW9:45 amChicago Midway
Nov 8
MDW1:06 pmChicago Midway
10h 21m
2 stops
SDQ1:27 amSanto Domingo Las Americas
$452
Find similar
Delta
Sep 6
SDQ3:03 pmSanto Domingo Las Americas
7h 09m
1 stop
MDW9:12 pmChicago Midway
Sep 15
MDW9:35 amChicago Midway
14h 01m
2 stops
SDQ12:36 amSanto Domingo Las Americas
$456
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Dominican Republic 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 August 20, 2025.
Use the filters below to find and compare flights from the Dominican Republic 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

Wed 9/10

5:05 pm-3:58 pm

2 stops23h 53m

Chicago Midway

Mon 9/15

8:19 am-12:15 pm

1 stop26h 56m

$417

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Mon 10/27

6:05 am-6:25 pm

2 stops13h 20m

Chicago Midway

Thu 10/30

6:00 am-1:41 pm

1 stop6h 41m

$450

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 11/5

2:49 pm-9:45 am

2 stops20h 56m

Chicago Midway

Sat 11/8

1:06 pm-1:27 am

2 stops10h 21m

$452

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 9/6

3:03 pm-9:12 pm

1 stop7h 09m

Chicago Midway

Mon 9/15

9:35 am-12:36 am

2 stops14h 01m

$456

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Sat 9/6

6:17 pm-12:44 pm

2 stops43h 27m

Chicago Midway

Fri 9/19

9:48 am-1:07 pm

1 stop26h 19m

$460

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/30

3:19 pm-10:03 pm

1 stop7h 44m

Chicago Midway

Wed 11/5

2:06 pm-2:56 pm

1 stop22h 50m

$473

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/16

3:14 pm-8:31 am

1 stop18h 17m

Chicago Midway

Wed 10/22

8:05 am-2:01 pm

1 stop28h 56m

$476

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Thu 10/30

3:19 pm-10:03 pm

1 stop7h 44m

Chicago Midway

Wed 11/5

2:06 pm-2:56 pm

1 stop22h 50m

$478

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Wed 9/10

12:25 pm-5:35 pm

2 stops30h 10m

Chicago Midway

Tue 9/16

12:43 pm-11:29 am

2 stops21h 46m

$3,583

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Sat 9/13

9:30 pm-1:03 pm

2 stops16h 33m

Chicago Midway

Tue 9/16

12:43 pm-11:29 am

2 stops21h 46m

$3,637

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 Dominican Republic 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

What is the cheapest Dominican Republic to Chicago Midway flight route?

Fly from Punta Cana to Chicago Midway for the best Dominican Republic - Chicago Midway flight prices

What cabin class options are available on Dominican Republic to Chicago Midway flights?

There are 1 cabin classes available to choose from on Dominican Republic to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Dominican Republic to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Dominican Republic to Chicago Midway Airport.

Cheap Dominican Republic to Chicago Midway Airport flight deals and tips

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

Fastest flight time

4h 55m

Direct flights

Sun
The fastest flight from Dominican Republic to Chicago Midway Airport takes 4h 55m
Direct flights go from Dominican Republic to Chicago Midway Airport on Sunday. There are no airlines offering direct flights.
Search flight deals

  • When did momondo last update prices for flights from Dominican Republic to Chicago Midway Airport?

    Prices for flights from Dominican Republic to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Dominican Republic 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 Dominican Republic 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.

  • What is the most popular plane model from Dominican Republic to Chicago Midway Airport?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Dominican Republic to Chicago?

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 Dominican Republic to Chicago for you.

Can I find flights from Dominican Republic to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Dominican Republic with this policy.

How can momondo help me find flights from Dominican Republic to Chicago?

Once all potential Dominican Republic to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Dominican Republic to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Dominican Republic and alert you when they change.

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