$209 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

Sat, Nov 21 - Sat, Nov 28
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
$310Arajet
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
$310Arajet
Thu, Jan 14 - Sun, Jan 31
Arajet Logo
7:30 pm - 10:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
3:20 am - 10:05 amORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$329Arajet
Thu, Oct 22 - Sat, Oct 31
Multiple Airlines Logo
3:30 pm - 11:40 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
9h 10m1 stop Punta Cana
Multiple Airlines Logo
11:27 am - 9:40 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
9h 13m1 stop Punta Cana
$370Multiple Airlines
Sat, Nov 21 - Sat, Nov 28
Multiple Airlines Logo
5:47 am - 8:57 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Multiple Airlines Logo
3:45 pm - 6:45 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
25h 00m1 stop Montreal Pierre Elliott Trudeau Intl
$375Multiple Airlines
Thu, Nov 12 - Thu, Nov 19
Multiple Airlines Logo
7:30 pm - 10:40 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Multiple Airlines Logo
7:25 am - 11:35 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
14h 10m2 stops Toronto Island Montreal Pierre Elliott Trudeau Intl
$375Multiple 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
Thu, Dec 24 - Thu, Dec 31
American Airlines Logo
5:34 pm - 9:08 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 34mnonstop
American Airlines Logo
9:52 am - 4:29 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 37mnonstop
$431American Airlines
Sat, Oct 3 - Sat, Oct 17
JetBlue Logo
3:30 pm - 11:08 pmSTI  Santiago de los Caballeros-ORD Chicago O'Hare Intl
8h 38m1 stop Fort Lauderdale
JetBlue Logo
7:00 am - 2:47 pmORD  Chicago O'Hare Intl-STI Santiago de los Caballeros
6h 47m1 stop Fort Lauderdale
$524JetBlue
Thu, Dec 3 - Sun, Dec 6
JetBlue Logo
2:42 pm - 11:28 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 46m1 stop Fort Lauderdale
JetBlue Logo
2:50 pm - 12:51 amORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
8h 01m1 stop Fort Lauderdale
$548JetBlue
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 $310 return. The most popular connection is from Punta Cana to Chicago and KAYAK users have found round-trip deals for as low as $310 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 $396. 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 $212 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 $499.

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 $116.

Good to know

Low season

January

Cheapest flight

$209
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 $310 return. The most popular connection is from Punta Cana to Chicago and KAYAK users have found round-trip deals for as low as $310 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 $587. 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 $285 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 12028 reviews
6.4Food
7.2Comfort
7.5Boarding
7.9Crew
6.8Entertainment
Airline reviews

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

10.0 ExcellentPeter, Aug 2026
Read more American Airlines reviews

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

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

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

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago