$198 Find Cheap Flights from the Dominican Republic to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from the Dominican Republic to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

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

Wed, Nov 4 - Sun, Nov 15
JetBlue Logo
4:31 pm - 11:57 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
9h 26m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 3:26 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
6h 26m1 stop Fort Lauderdale
$336JetBlue
Sat, Nov 21 - Sat, Nov 28
Arajet Logo
7:00 am - 10:10 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
11:10 am - 5:55 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$366Arajet
Tue, Nov 10 - Tue, Nov 17
JetBlue Logo
2:50 pm - 11:36 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
10h 46m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 3:26 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
6h 26m1 stop Fort Lauderdale
$372JetBlue
Sat, Nov 21 - Sat, Nov 28
Arajet Logo
7:00 am - 10:10 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
11:10 am - 5:55 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$373Arajet
Sat, Nov 21 - Sat, Nov 28
Arajet Logo
7:00 am - 10:10 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
11:10 am - 5:55 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$376Arajet
Tue, Nov 10 - Tue, Nov 17
JetBlue Logo
2:50 pm - 11:36 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
10h 46m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 3:26 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
6h 26m1 stop Fort Lauderdale
$377JetBlue
Mon, Dec 21 - Mon, Dec 28
United Airlines Logo
4:25 pm - 7:41 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 16mnonstop
United Airlines Logo
9:43 pm - 4:04 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
16h 21m1 stop Houston George Bush Intcntl
$378United Airlines
Fri, Dec 18 - Sun, Jan 3
Multiple Airlines Logo
1:40 am - 10:10 amSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 30m1 stop Punta Cana
Multiple Airlines Logo
4:20 am - 4:45 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
10h 25m1 stop Punta Cana
$390Multiple Airlines
Fri, Dec 25 - Fri, Jan 1
American Airlines Logo
3:48 pm - 7:21 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 33mnonstop
American Airlines Logo
9:52 am - 4:29 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 37mnonstop
$396American Airlines
Thu, Nov 5 - Thu, Nov 12
American Airlines Logo
3:59 pm - 7:30 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 31mnonstop
American Airlines Logo
9:11 pm - 3:37 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
16h 26m1 stop Philadelphia
$401American Airlines
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Chicago?

In the last 5 days, the cheapest flight deal to Chicago was found on the route from Punta Cana, at $336 return. The most popular connection is from Santo Domingo to Chicago and KAYAK users have found round-trip deals for as low as $390 in the last 5 days.

What is the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Sunday where round-trip tickets can be as cheap as $386. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $509 on average.

What is the cheapest month to fly to Chicago?

The cheapest month for flights to Chicago is February, where tickets cost $375 on average for return flights. On the other hand, the most expensive months are March and June, where the average cost of tickets from the Dominican Republic is $801 and $671 respectively. For one-way flights, the best month to travel is December with an average price of $219.

What is the cheapest time of day to fly to Chicago?

The cheapest time of day to fly to Chicago is generally at night, when round-trip flights cost $236 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $535.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Punta Cana $303 round-trip.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $150.

Good to know

Low season

January

Cheapest flight

$198
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Punta Cana to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 5 days, the cheapest flight deal to Chicago was found on the route from Punta Cana, at $336 return. The most popular connection is from Santo Domingo to Chicago and KAYAK users have found round-trip deals for as low as $390 in the last 5 days.

  • Which Chicago airport is closest to central Chicago?

    9 miles away from Chicago’s city center, Chicago Midway Airport is the closest of the 3 major airports in the city. There are 16 miles separating Chicago city center to Chicago O'Hare Airport, and 79 miles to Chicago Greater Rockford.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $399. The cheapest price found on KAYAK in the last 2 weeks cost $189 and departed from Punta Cana Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $293 or less one-way and $303 or less round-trip.

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airline flying from the Dominican Republic to Chicago

 
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.0
American AirlinesOverall score based on 12158 reviews
7.4Boarding
7.2Comfort
6.8Entertainment
6.4Food
7.9Crew
Airline reviews

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

2.0 MediocreAnonymous, Oct 2026
Read more American Airlines reviews

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

12 hour wait in pdx to my initial flight to Dallas to hunstville

The flight from Chicago to Orlando was delayed inordinately. My whole journey from Lansing to MCO took 9.5 hours is just annoying and frustrating. We can understand the delays may be beyond their control, but overall the journey was so much waiting until reached to MCO. This is NOT the first time for me - but at least 80% of the time in this route. I barely remember reaching places on time.

I was truly shocked at how poor this flight went. The crew was not friendly during the checking process. The asked for people to gate check and were rude about it. They didn't handle my luggage with care. When I got to my seat I noticed a large section of the ceiling vent area was, no joke, TAPED TOGETHER WITH CLEAR PACKING TAPE! To add insult to injury, the back rest button was disabled on my seat and all the seats I could see. The wifi, never connected for me, despite troubleshooting it for a while. I did everything from restarting my wifi/phone to forgetting the network and restarting the app. But that didn't stop the mandatory 2 ads from playing every single time. Even the bags took over 45 mins to arrive at the carousel. Everything about this flight was a flop and I am beginning to notice that some of these events are becoming a trend. Perhaps it's time I switch loyalty programs.

Horrible airline, will never buy another ticket with the airline or Kayak. They close the gate 2 hours early in Kenya, I had to buy a new ticket and get a hotel room

It would be helpful to be able to download an eticket from either American airlines or Cathay Pacific; not just Cathay Pacific.

Another American Airlines flight, another significant delay. At least this one wasn't canceled like many others have been. This time we sat on the runway at LaGuardia for 2.5 hours. By my count that is 7 American flights the last three months that have been delayed 2 hours or more or canceled entirely.

There was no clear update on the flight until last minute and made it an hour delay. No clear flight aircraft or incoming flight which we will be boarding. We would plan accordingly for our connecting flight. This is one one the worst service, I also had to buy an another ticket with different ai carrier. American airline was not letting me plan my trip, made us just waiting. Not a good service at all.

The plane was delayed after we boarded - although they sent an email to my work email (which I did not get until later) there was no announcement from the PA about the delay in flight. Fortunately, they made up the time in the air and we landed around the original time.

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Traveling to a place near Chicago?

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

More options for your flight to Chicago