$185 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, Dec 19 - Fri, Jan 8
Arajet Logo
7:00 am - 10:10 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
5:45 am - 12:30 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$264Arajet
Sun, Nov 22 - Sun, Nov 29
Arajet Logo
7:10 pm - 10:20 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
4:20 am - 11:05 amORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$285Arajet
Sat, Dec 19 - Sun, Jan 3
Arajet Logo
7:00 am - 10:10 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Arajet Logo
4:20 am - 11:05 amORD  Chicago O'Hare Intl-PUJ Punta Cana
4h 45mnonstop
$296Arajet
Sat, Dec 19 - Fri, Jan 8
Multiple Airlines Logo
3:50 pm - 10:28 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
8h 38m1 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
$332Multiple Airlines
Sat, Nov 7 - Sat, Nov 14
Multiple Airlines Logo
7:00 am - 10:10 amPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 10mnonstop
Multiple Airlines Logo
7:15 am - 11:36 amORD  Chicago O'Hare Intl-PUJ Punta Cana
26h 21m2 stops Atlanta Hartsfield-Jackson Miami
$351Multiple Airlines
Fri, Nov 6 - Sat, Nov 14
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
11:10 am - 9:40 pmORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
8h 30m1 stop Punta Cana
$355Multiple Airlines
Fri, Dec 25 - Fri, Jan 1
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
$372American Airlines
Sat, Nov 21 - Sat, Nov 28
American Airlines Logo
5:09 pm - 8:43 pmPUJ  Punta Cana-ORD Chicago O'Hare Intl
5h 34mnonstop
American Airlines Logo
6:00 am - 3:48 pmORD  Chicago O'Hare Intl-PUJ Punta Cana
7h 48m1 stop Miami
$377American Airlines
Wed, Dec 2 - Mon, Dec 7
JetBlue Logo
2:43 pm - 11:33 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
10h 50m1 stop Fort Lauderdale
JetBlue Logo
2:59 pm - 1:15 amORD  Chicago O'Hare Intl-SDQ Santo Domingo Las Americas
8h 16m1 stop Fort Lauderdale
$543JetBlue
Tue, Nov 17 - Tue, Nov 24
JetBlue Logo
2:32 pm - 11:36 pmSDQ  Santo Domingo Las Americas-ORD Chicago O'Hare Intl
11h 04m1 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
$543JetBlue
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 $264 return. The most popular connection is from Santo Domingo to Chicago and KAYAK users have found round-trip deals for as low as $355 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 $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 $509.

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

$185
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 9% 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 $264 return. The most popular connection is from Santo Domingo to Chicago and KAYAK users have found round-trip deals for as low as $355 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 $379. The cheapest price found on KAYAK in the last 2 weeks cost $167 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.

  • How many direct flights to Chicago are there each week?

    Each week there are around 33,181 direct flights from within Dominican Republic to Chicago. The most common day for departures is Sunday, with 16% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $280 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 12097 reviews
6.4Food
7.4Boarding
7.9Crew
7.2Comfort
6.8Entertainment
Airline reviews

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.

8.0 ExcellentLynne, Sep 2026
Read more American Airlines reviews

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.

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

My experience was fine, with one surprising exception. After leveling off at cruising altitude, the main cabin flight attendant made an announcement that he had a cold, so he would not be coming through the aisle to provide cabin service. He claimed this was in consideration of his health and safety and ours. However, if passengers wanted a beverage, he invited them to come to the back of he plane, where he would provide service. I understand that a flight attendant's primary responsibility is to ensure passenger safety, but a secondary role is to provide service. If this flight attendant was too sick to perform his duties - and if he truly cared about passenger health and safety , as he claimed - he should have stayed home and called in sick, rather than exposing the cabin to his germs.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

We waited over 30 minutes for a gate in Chicago and more than 15 minutes for the doors to open. Cookies were missing from the menu.

Flight was 2 hr late but at least I was upgraded to first class

The flight was delay roughly 90 minutes. Once we arrived at O'Hare, we sat on the tarmac for another 90 minutes. I understand that O'Hare is under construction however they need to figure out a solution as every incoming flight I have been on has been delayed coming to a gate.

We were stuck with no gate upon landing for 90 minutes. Unacceptable.

Horrible. Flight was delayed for 4 hours first till 7pm. Then for one more hour. Then again and around 9pm we were finally boarded and waited for catering delivery for another hour. At 10pm we were not interested on food at all. Tired, sleepy we arrived after midnight. Insane.

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
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
Griffith

More options for your flight to Chicago