$208 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
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
$336Arajet
Thu, Apr 15 - Sat, Apr 24
Arajet Logo
7:15 pm - 11:25 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
12:12 pm - 5:57 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$347Arajet
Thu, Apr 15 - Fri, Apr 30
Arajet Logo
7:15 pm - 11:25 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
6:45 am - 12:30 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$347Arajet
Sun, Dec 13 - Sun, Jan 10
Frontier Logo
1:27 pm - 8:24 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
8h 57m1 stop Philadelphia
Frontier Logo
10:31 pm - 5:20 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
16h 49m1 stop San Juan Luis Munoz Marin Intl
$397Frontier
Thu, Dec 3 - Wed, Dec 9
Frontier Logo
2:33 pm - 9:18 amSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
20h 45m1 stop Orlando
Frontier Logo
5:24 pm - 1:10 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
17h 46m1 stop Orlando
$398Frontier
Fri, Dec 18 - Fri, Jan 8
Multiple Airlines Logo
7:15 pm - 1:33 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
8h 18m1 stop San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
5:45 am - 12:30 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$400Multiple 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
6:45 am - 3:46 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
7h 01m1 stop Philadelphia
$440American Airlines
Fri, Jan 22 - Sun, Jan 31
American Airlines Logo
5:41 pm - 9:13 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 32mnonstop
American Airlines Logo
9:35 am - 4:20 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$444American Airlines
Wed, Dec 2 - Tue, Jan 5
JetBlue Logo
2:43 pm - 11:33 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 50m1 stop Fort Lauderdale
JetBlue Logo
2:55 pm - 2:05 amORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
9h 10m1 stop Boston Logan Intl
$502JetBlue
Fri, Nov 20 - Sun, Nov 22
JetBlue Logo
5:01 am - 1:32 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 31m1 stop Fort Lauderdale
JetBlue Logo
2:59 pm - 12:59 amORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
8h 00m1 stop Fort Lauderdale
$572JetBlue
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 $397 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 $393. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $589 on average.

What is the cheapest month to fly to Chicago?

The cheapest month for flights to Chicago is February, where tickets cost $358 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 $781 and $679 respectively. For one-way flights, the best month to travel is December with an average price of $218.

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 $250 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 $553.

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 $377 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 $135.

Good to know

Low season

November

Cheapest flight

$208
Best time to beat the crowds with an average 1% 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 $397 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 $188 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 $248 or less one-way and $377 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 12225 reviews
7.4Boarding
7.2Comfort
6.8Entertainment
6.4Food
7.9Crew
Airline reviews

WiFi broken, very long wait for valet bags, and the typical long wait at O'Hare on a thursday to get clearance to take off and then again long taxi and wait for the gate.

6.0 GoodJulie, Nov 2026
Read more American Airlines reviews

WiFi broken, very long wait for valet bags, and the typical long wait at O'Hare on a thursday to get clearance to take off and then again long taxi and wait for the gate.

Another American flight, another significant non weather related delay. Was delayed over 90 minutes on both legs of the round trip.

The now boarding notification was not updated in the app until I was actually on the plan. This si a massive fail considering my flight was delayed several times. These types of failures add stress that could be avoided since I no longer feel comfortable leaving the boarding area to get food or visit a lounge. Had I used the notification from the app, I would have missed my flight. The secondly, the process of connecting to wifi on aa flights is clunky and could be streamlined better. the copy and past process feels like MVP, and you are well beyond that stage.

Both flights were late leaving due to repairs/switching gates. The crew and pilots, however, were professional and courteous. Most importantly, we arrived at our destination safely. The seats were comforable. That size should be standard for all economy class. American could improve its boarding process. I am not sure why you need 9 groups for a small regional plane.

It was close to its perfect the flake could be took off early, landed early, didn’t have to wait for my daughter stroller luggage came out quick, very efficient, very good flight

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.

No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.

Same the delay was not ideal and the credits to move flights was not sufficient

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
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