$188 Find Cheap Flights from the Dominican Republic to Chicago - Compare and Save

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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

Thu, Sep 24 - Mon, Sep 28
Arajet Logo
7:30 pm - 11:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
5:30 am - 11:15 amORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$322Arajet
Sat, Nov 7 - Sat, Nov 14
Arajet Logo
5:47 am - 8:57 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
10:27 am - 5:12 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$346Arajet
Sat, Oct 31 - Sat, Nov 7
Arajet Logo
5:47 am - 9:57 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
10:27 am - 5:12 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$346Arajet
Thu, Oct 22 - Mon, Oct 26
Multiple Airlines Logo
1:45 pm - 11:40 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 55m1 stop Punta Cana
Multiple Airlines Logo
4:30 am - 4:55 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
11h 25m1 stop Punta Cana
$370Multiple Airlines
Thu, Sep 17 - Fri, Sep 25
Multiple Airlines Logo
7:30 pm - 11:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Multiple Airlines Logo
3:40 pm - 4:05 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
23h 25m1 stop Montreal Pierre Elliott Trudeau Intl
$371Multiple Airlines
Mon, Oct 26 - Sun, Nov 1
Multiple Airlines Logo
2:15 pm - 11:07 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
21h 52m1 stop Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
3:20 am - 10:05 amORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$378Multiple Airlines
Thu, Dec 24 - Sat, Jan 2
American Airlines Logo
5:34 pm - 9:08 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 34mnonstop
American Airlines Logo
9:30 am - 4:10 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 40mnonstop
$431American Airlines
Thu, Dec 24 - Fri, Jan 1
American Airlines Logo
5:34 pm - 9:08 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 34mnonstop
American Airlines Logo
8:10 am - 2:48 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 38mnonstop
$431American Airlines
Sat, Oct 10 - Thu, Oct 15
JetBlue Logo
2:57 pm - 11:52 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
9h 55m1 stop Atlanta Hartsfield-Jackson
JetBlue Logo
5:27 am - 1:32 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
7h 05m1 stop Atlanta Hartsfield-Jackson
$514JetBlue
Thu, Nov 5 - Wed, Nov 11
JetBlue Logo
3:57 pm - 11:57 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 00m1 stop Atlanta Hartsfield-Jackson
JetBlue Logo
5:30 am - 2:40 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
7h 10m1 stop Atlanta Hartsfield-Jackson
$514JetBlue
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 Santo Domingo, at $322 return. The most popular connection is from Punta Cana to Chicago and KAYAK users have found round-trip deals for as low as $322 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 Wednesday where round-trip tickets can be as cheap as $359. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $506 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 $216.

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 $496.

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 $490 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 $120.

Good to know

Low season

January

Cheapest flight

$188
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Santo Domingo to Chicago

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 Santo Domingo, at $322 return. The most popular connection is from Punta Cana to Chicago and KAYAK users have found round-trip deals for as low as $322 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 $527. The cheapest price found on KAYAK in the last 2 weeks cost $198 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 $271 or less one-way and $490 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.
7.1
American AirlinesOverall score based on 11974 reviews
6.4Food
7.9Crew
7.5Boarding
6.8Entertainment
7.2Comfort
Airline reviews

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

6.0 GoodAnonymous, Aug 2026
Read more American Airlines reviews

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Missed connection from delays and times changing multiple times and then involuntarily booked on another airline next day

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

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
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Munster
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago