$127 Find Cheap Flights from the Dominican Republic to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 2/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$268
Spirit Airlines
Wed 4/8Mon 4/13
STI - ORD • 1 stop
Cheapest non-stop
$267
Typical prices: $227-$486
Arajet
Sat 5/2Sat 5/16
PUJ - ORD • Non-stop
Top airlines
American Airlines
Most flights • 17 per week
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 38% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from the Dominican Republic to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from the Dominican Republic to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
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, Apr 8 - Mon, Apr 13
Spirit Airlines Logo
3:43 pm - 11:17 pm
STI
-
ORD
8h 34m
1 stop
Spirit Airlines Logo
5:05 am - 2:35 pm
ORD
-
STI
8h 30m
1 stop
$268Spirit Airlines
Thu, Feb 19 - Sun, Feb 22
Spirit Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m
1 stop
Spirit Airlines Logo
7:00 am - 4:36 pm
ORD
-
PUJ
7h 36m
1 stop
$269Spirit Airlines
Sat, Feb 7 - Sun, Feb 8
Spirit Airlines Logo
5:47 pm - 11:47 pm
PUJ
-
ORD
8h 00m
1 stop
Spirit Airlines Logo
5:15 am - 4:36 pm
ORD
-
PUJ
9h 21m
1 stop
$272Spirit Airlines
Sat, Feb 21 - Mon, Mar 2
Arajet Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
Arajet Logo
5:45 am - 12:30 pm
ORD
-
PUJ
4h 45mnonstop
$275Arajet
Sat, Feb 14 - Sun, Feb 15
Multiple Airlines Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
7:00 am - 4:36 pm
ORD
-
PUJ
7h 36m
1 stop
$276Multiple Airlines
Sat, Feb 21 - Sun, Feb 22
Multiple Airlines Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
7:00 am - 4:36 pm
ORD
-
PUJ
7h 36m
1 stop
$279Multiple Airlines
Sat, Feb 14 - Sun, Feb 15
Multiple Airlines Logo
5:47 am - 8:57 am
PUJ
-
ORD
5h 10mnonstop
Multiple Airlines Logo
7:00 am - 4:36 pm
ORD
-
PUJ
7h 36m
1 stop
$281Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
Delta Logo
7:30 am - 5:45 pm
SDQ
-
MDW
12h 15m
2 stops
Delta Logo
10:49 am - 12:32 am
MDW
-
SDQ
11h 43m
2 stops
$477Delta
Fri, Feb 6 - Sun, Feb 8
Delta Logo
3:46 pm - 10:22 pm
SDQ
-
MDW
8h 36m
1 stop
Delta Logo
6:00 am - 2:21 pm
MDW
-
SDQ
6h 21m
1 stop
$489Delta
Thu, Mar 12 - Thu, Mar 19
Frontier Logo
4:11 pm - 1:08 pm
PUJ
-
MDW
21h 57m
2 stops
Frontier Logo
6:00 am - 3:06 pm
MDW
-
PUJ
32h 06m
2 stops
$650Frontier
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 month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Chicago is February, where tickets cost $270 on average for one-way flights. On the other hand, the most expensive months are June and October, where the average cost of tickets from the Dominican Republic is $772 and $628 respectively. For return trips, the best month to travel is February with an average price of $270.

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 $326 one-way - $160 round-trip.

How far in advance should I book a flight to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price, you should book around 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 27 days before departure.

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, with an average flight price of $138.

Good to know

Low seasonJune
Cheapest flight$127
Best time to beat the crowds but there is an average 36% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Santiago de los Caballeros to Chicago

FAQs - booking Chicago flights

  • 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 $415. The cheapest price found on KAYAK in the last 2 weeks cost $116 and departed from Punta Cana Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Friday where tickets can be as cheap as $345. On the other hand, the most expensive day to fly is Monday, where prices are $521 on average.

  • 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.

  • 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 flights cost $258 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $426.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $326 or less one-way and $160 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 airlines flying from the Dominican Republic to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the Dominican Republic to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
7.2
American AirlinesOverall score based on 11197 reviews
6.4Food
7.2Comfort
8.0Crew
6.9Entertainment
7.5Boarding
Airline reviews

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

10.0 Excellentaras, Jan 2026
PIT - ORD
Read more American Airlines reviews

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

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
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.