$149 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 4/21. 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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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

Sat, May 9 - Sat, May 16
Frontier Logo
3:35 pm - 7:55 am
PUJ
-
ORD
17h 20m
1 stop
Frontier Logo
7:52 pm - 10:57 am
ORD
-
PUJ
14h 05m
1 stop
$263Frontier
Fri, May 1 - Mon, May 4
Spirit Airlines Logo
3:54 pm - 12:24 am
PUJ
-
ORD
9h 30m
1 stop
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
PUJ
7h 25m
1 stop
$264Spirit Airlines
Sat, May 9 - Sat, May 16
Frontier Logo
3:35 pm - 7:55 am
PUJ
-
ORD
17h 20m
1 stop
Frontier Logo
7:52 pm - 10:57 am
ORD
-
PUJ
14h 05m
1 stop
$273Frontier
Fri, May 1 - Mon, May 11
Spirit Airlines Logo
3:54 pm - 12:24 am
PUJ
-
ORD
9h 30m
1 stop
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
PUJ
7h 25m
1 stop
$282Spirit Airlines
Thu, Apr 23 - Wed, Apr 29
Spirit Airlines Logo
2:35 pm - 12:24 am
SDQ
-
ORD
10h 49m
1 stop
Spirit Airlines Logo
7:15 pm - 1:29 pm
ORD
-
SDQ
17h 14m
1 stop
$283Spirit Airlines
Fri, May 1 - Sun, May 10
Frontier Logo
1:37 pm - 10:26 pm
PUJ
-
MDW
9h 49m
2 stops
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
$288Frontier
Fri, May 1 - Sun, May 10
Multiple Airlines Logo
3:54 pm - 11:54 pm
PUJ
-
ORD
9h 00m
1 stop
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
PUJ
7h 25m
1 stop
$305Multiple Airlines
Fri, May 1 - Mon, May 4
Multiple Airlines Logo
9:13 pm - 3:23 pm
PUJ
-
ORD
19h 10m
2 stops
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
PUJ
7h 25m
1 stop
$308Multiple Airlines
Sat, May 2 - Wed, May 6
Delta Logo
6:05 am - 4:26 pm
SDQ
-
MDW
11h 21m
2 stops
Delta Logo
1:24 pm - 12:17 am
MDW
-
SDQ
9h 53m
2 stops
$561Delta
Thu, Apr 23 - Wed, Apr 29
Delta Logo
6:05 am - 4:26 pm
SDQ
-
MDW
11h 21m
2 stops
Delta Logo
10:41 am - 12:17 am
MDW
-
SDQ
12h 36m
2 stops
$579Delta
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?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Santo Domingo, at $263 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $118 in the last 3 days.

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Friday where round-trip tickets can be as cheap as $318. 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?

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 November, where tickets cost $344 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 $849 and $772 respectively. For one-way flights, the best month to travel is November with an average price of $344.

What is the cheapest time of day to fly to Chicago?

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago is generally at night, when round-trip flights cost $258 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 $473.

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 $380 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 2 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks 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 (RFD), with an average flight price of $160.

Good to know

Low seasonJanuary
Cheapest flight$149
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Santo Domingo to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Santo Domingo, at $263 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $118 in the last 3 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 $467. The cheapest price found on KAYAK in the last 2 weeks cost $180 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 $345 or less one-way and $380 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

 
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.
7.1
American AirlinesOverall score based on 11564 reviews
6.4Food
7.5Boarding
7.2Comfort
7.9Crew
6.8Entertainment
Airline reviews

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

2.0 MediocreMark, Apr 2026
PHX - ORD
Read more American Airlines reviews

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

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.