Cheap Flights from Chicago to Punta Cana
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Prices updated 24 days ago
486,190 searches this week
171 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from Chicago to Punta Cana
Explore current cheapest deals departing from Chicago to Punta Cana
Round trip
Sort by: Cheapest
September 4 - September 6
ORD - Punta Cana
$725
$288
Round trip
September 4 - September 12
ORD - Punta Cana
$680
$288
Round trip
October 16 - October 18
ORD - Punta Cana
$581
$294
Round trip
November 6 - November 8
ORD - Punta Cana
$496
$295
Round trip
October 5 - October 15
ORD - Punta Cana
$523
$296
Round trip
October 19 - November 8
ORD - Punta Cana
$517
$296
Round trip
November 2 - November 12
ORD - Punta Cana
$466
$296
Round trip
November 2 - November 19
ORD - Punta Cana
$444
$296
Round trip
October 30 - November 5
ORD - Punta Cana
$579
$296
Round trip
October 5 - October 22
ORD - Punta Cana
$500
$296
Round trip
Unlock all 500+ flight deals to Punta Cana and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Chicago to Punta Cana
How much is a round trip from Chicago to Punta Cana
Regular price: $531 - $1,367
Prices are currently below the regular range.
The regular price range for flights from Chicago to Punta Cana is $531 to $1,367. The current lowest deal is $288 with Maersk Air. This deal is available for travel from Sep 4-Sep 6.
now $288
Low $531
High $1,367
The cheapest time to fly from Chicago to Punta Cana
The cheapest month to fly from Chicago to Punta Cana is May, with a median price of $209. The most expensive month is November, with a median price of $744. Prices are generally lower from January to September.
May
Flights from $209
November
Flights from $744
Direct flights from Chicago to Punta Cana
Maersk Air
Last-minute flights going from Chicago to Punta Cana
Mon, Aug 17
ORD - Punta Cana
Chicago (ORD) - Punta Cana (PUJ)
Maersk Air
$346
$314
One-way
Mon, Aug 17
ORD - Punta Cana
Chicago (ORD) - Punta Cana (PUJ)
Maersk Air
$350
$314
One-way
Mon, Aug 17
ORD - Punta Cana
Chicago (ORD) - Punta Cana (PUJ)
Maersk Air
$385
$327
One-way
Sat, Aug 29
ORD - Punta Cana
Chicago (ORD) - Punta Cana (PUJ)
Maersk Air
$394
$296
One-way
Sat, Aug 29
ORD - Punta Cana
Chicago (ORD) - Punta Cana (PUJ)
Maersk Air
$347
$296
One-way
Sat, Aug 29
ORD - Punta Cana
Chicago (ORD) - Punta Cana (PUJ)
Maersk Air
$359
$296
One-way
Biggest price drops on these dates for flights from Chicago to Punta Cana
Sep 4 - Sep 6
$725 → $288
60%
Sep 21 - Sep 27
$734 → $300
59%
Sep 19 - Sep 26
$722 → $296
59%
Sep 7 - Sep 12
$730 → $304
58%
Popular Airports to fly from Chicago to Punta Cana
Chicago - Punta Cana route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from Chicago to Punta Cana are below the typical level at $288.
📅 Best time to fly
Fly in May for the cheapest fares
Historically, May is the cheapest month to fly from Chicago to Punta Cana, with a median price of $209.
⏱️ Flight duration
Expect a 9h 55m flight
The median flight duration from Chicago to Punta Cana is 9 hours and 55 minutes.
✈️ Airlines & availability
Maersk Air offers direct flights
Maersk Air has offered direct flights from Chicago to Punta Cana in recent deals.
🏆 Airline highlight
Maersk Air: 1 direct deal
Maersk Air has offered 1 direct deal from Chicago to Punta Cana in recent deals.
🎯 Booking tip
Deals are frequent for this route
Deals for flights from Chicago to Punta Cana are frequent, with over 1 deal per day.
Chicago main airports to depart from
O Hare International (ORD)
Consider O'Hare International for flights to Punta Cana, offering the cheapest available prices from Chicago.
📍 ~20 km from city center (reachable by car or train)
💸 Flights from ~$288
Chicago Midway International (MDW)
Chicago Midway International provides another option for travelers flying from Chicago to Punta Cana.
📍 ~15 km from city center (reachable by car or train)
💸 Flights from ~$448
Chicago Rockford International (RFD)
Chicago Rockford International is an alternative departure point for your trip to Punta Cana.
📍 ~110 km from city center (reachable by car)
💸 Flights from ~$416
Punta Cana main airports to arrive at
Punta Cana International (PUJ)
Punta Cana International Airport is a convenient arrival point for your trip to Punta Cana.
📍 ~5 km from Punta Cana (reachable by car)
💸 Flights from ~$288
Airports nearby Punta Cana used as alternative
Las Américas International (SDQ)
Las Américas International is the primary international hub for the Dominican Republic, offering a wide range of carriers.
📍 ~135 km from Punta Cana (reachable by car, approximately 2.5 to 3-hour drive).
💸 Flights from ~$338
La Romana International (LRM)
La Romana International is the closest alternative airport to Punta Cana, with easy road access.
📍 ~70 km from Punta Cana (reachable by car).
💸 Flights from ~$577
Cibao International (STI)
Cibao International is a major international airport serving the northern region with good North American connectivity.
📍 ~250 km from Punta Cana (reachable by car, approximately 4-5 hours drive).
💸 Flights from ~$404
Samaná El Catey International (AZS)
Samaná El Catey International serves specific international leisure routes within the eastern/northern region.
📍 ~180 km from Punta Cana (reachable by car).
💸 Flights from ~$876
La Isabela International (JBQ)
La Isabela International is a secondary airport in the capital, useful for regional Caribbean connections.
📍 ~150 km from Punta Cana (reachable by car).
💸 Flights from ~$844
Business & First Class Flight Deals to Punta Cana
Discover luxury on the budget with premium cabin class on flights from Chicago to Punta Cana.
Elite
Best Elite deals to Punta Cana
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From ORD
Elite
Aug 01
Punta Cana, Dominican Republic
91% AI deal score
$1,931
$943
Save $988
From ORD
Elite
Jul 31
Punta Cana, Dominican Republic
90% AI deal score
$1,828
$920
Save $908
From ORD
Elite
Jul 13
Punta Cana, Dominican Republic
88% AI deal score
$1,811
$989
Save $822
From ORD
Elite
Oct 20
Punta Cana, Dominican Republic
83% AI deal score
$1,856
$1,246
Save $610
From ORD
Elite
Aug 10
Punta Cana, Dominican Republic
78% AI deal score
$1,640
$1,241
Save $399
From ORD
Elite
Dec 05
Punta Cana, Dominican Republic
77% AI deal score
$1,615
$1,241
Save $374
From ORD
Elite
Dec 11
Punta Cana, Dominican Republic
77% AI deal score
$1,637
$1,248
Save $389
From ORD
Elite
Dec 12
Punta Cana, Dominican Republic
77% AI deal score
$1,645
$1,264
Save $381
From ORD
Elite
Aug 22
Punta Cana, Dominican Republic
77% AI deal score
$1,631
$1,265
Save $366
From ORD
Elite
Aug 15
Punta Cana, Dominican Republic
77% AI deal score
$1,630
$1,265
Save $365
From ORD
Elite
Dec 12
Punta Cana, Dominican Republic
77% AI deal score
$1,636
$1,271
Save $365
From ORD
Elite
Aug 29
Punta Cana, Dominican Republic
77% AI deal score
$1,641
$1,275
Save $366
From ORD
Elite
Dec 11
Punta Cana, Dominican Republic
77% AI deal score
$1,678
$1,298
Save $380
From ORD
Elite
Oct 27
Punta Cana, Dominican Republic
76% AI deal score
$1,557
$1,227
Save $330
From ORD
Elite
Oct 24
Punta Cana, Dominican Republic
76% AI deal score
$1,562
$1,241
Save $321
From ORD
Elite
Jul 11
Punta Cana, Dominican Republic
76% AI deal score
$1,537
$1,248
Save $289
From ORD
Elite
Oct 04
Punta Cana, Dominican Republic
76% AI deal score
$1,540
$1,251
Save $289
From ORD
Elite
Oct 24
Punta Cana, Dominican Republic
76% AI deal score
$1,603
$1,251
Save $352
From ORD
Elite
Oct 30
Punta Cana, Dominican Republic
76% AI deal score
$1,599
$1,264
Save $335
From ORD
Elite
Oct 24
Punta Cana, Dominican Republic
76% AI deal score
$1,562
$1,275
Save $287
From ORD
Elite
Oct 30
Punta Cana, Dominican Republic
76% AI deal score
$1,630
$1,288
Save $342
From ORD
Elite
Dec 04
Punta Cana, Dominican Republic
76% AI deal score
$1,608
$1,288
Save $320
From ORD
Elite
Dec 05
Punta Cana, Dominican Republic
76% AI deal score
$1,617
$1,298
Save $319
From ORD
Elite
Dec 05
Punta Cana, Dominican Republic
76% AI deal score
$1,616
$1,298
Save $318
From ORD
Elite
Dec 04
Punta Cana, Dominican Republic
76% AI deal score
$1,610
$1,298
Save $312
From ORD
Elite
Dec 06
Punta Cana, Dominican Republic
76% AI deal score
$1,618
$1,323
Save $295
From ORD
Elite
Dec 07
Punta Cana, Dominican Republic
76% AI deal score
$1,659
$1,323
Save $336
From ORD
Elite
Dec 10
Punta Cana, Dominican Republic
76% AI deal score
$1,631
$1,333
Save $298
From ORD
Elite
Dec 10
Punta Cana, Dominican Republic
76% AI deal score
$1,630
$1,336
Save $294
From ORD
Elite
Dec 11
Punta Cana, Dominican Republic
76% AI deal score
$1,645
$1,357
Save $288
From ORD
Elite
Nov 27
Punta Cana, Dominican Republic
75% AI deal score
$1,449
$1,241
Save $208
From ORD
Elite
Nov 07
Punta Cana, Dominican Republic
75% AI deal score
$1,478
$1,251
Save $227
From ORD
Elite
Nov 16
Punta Cana, Dominican Republic
75% AI deal score
$1,467
$1,264
Save $203
From ORD
Elite
Nov 16
Punta Cana, Dominican Republic
75% AI deal score
$1,466
$1,264
Save $202
From ORD
Elite
Jul 19
Punta Cana, Dominican Republic
75% AI deal score
$1,530
$1,271
Save $259
From ORD
Elite
Nov 06
Punta Cana, Dominican Republic
75% AI deal score
$1,477
$1,274
Save $203
From ORD
Elite
Sep 19
Punta Cana, Dominican Republic
75% AI deal score
$1,497
$1,275
Save $222
From ORD
Elite
Sep 05
Punta Cana, Dominican Republic
75% AI deal score
$1,504
$1,275
Save $229
From ORD
Elite
Oct 03
Punta Cana, Dominican Republic
75% AI deal score
$1,545
$1,288
Save $257
From ORD
Elite
Oct 30
Punta Cana, Dominican Republic
75% AI deal score
$1,558
$1,321
Save $237
From ORD
Elite
Oct 25
Punta Cana, Dominican Republic
75% AI deal score
$1,598
$1,323
Save $275
From ORD
Elite
Oct 28
Punta Cana, Dominican Republic
75% AI deal score
$1,557
$1,323
Save $234
From ORD
Elite
Sep 27
Punta Cana, Dominican Republic
75% AI deal score
$1,544
$1,326
Save $218
From ORD
Elite
Oct 29
Punta Cana, Dominican Republic
75% AI deal score
$1,557
$1,326
Save $231
From ORD
Elite
Oct 29
Punta Cana, Dominican Republic
75% AI deal score
$1,558
$1,336
Save $222
From ORD
Elite
Dec 07
Punta Cana, Dominican Republic
75% AI deal score
$1,618
$1,340
Save $278
From ORD
Elite
Oct 29
Punta Cana, Dominican Republic
75% AI deal score
$1,599
$1,350
Save $249
From ORD
Elite
Oct 28
Punta Cana, Dominican Republic
75% AI deal score
$1,629
$1,357
Save $272
From ORD
Elite
Nov 28
Punta Cana, Dominican Republic
74% AI deal score
$1,450
$1,288
Save $162
From ORD
Elite
Nov 13
Punta Cana, Dominican Republic
74% AI deal score
$1,474
$1,288
Save $186
From ORD
Elite
Nov 28
Punta Cana, Dominican Republic
74% AI deal score
$1,449
$1,298
Save $151
From ORD
Elite
Nov 01
Punta Cana, Dominican Republic
74% AI deal score
$1,492
$1,323
Save $169
From ORD
Elite
Nov 29
Punta Cana, Dominican Republic
74% AI deal score
$1,449
$1,323
Save $126
From ORD
Elite
Nov 16
Punta Cana, Dominican Republic
74% AI deal score
$1,467
$1,326
Save $141
From ORD
Elite
Nov 15
Punta Cana, Dominican Republic
74% AI deal score
$1,516
$1,333
Save $183
From ORD
Elite
Nov 11
Punta Cana, Dominican Republic
74% AI deal score
$1,474
$1,333
Save $141
From ORD
Elite
Jul 10
Punta Cana, Dominican Republic
74% AI deal score
$1,495
$1,333
Save $162
From ORD
Elite
Jul 29
Punta Cana, Dominican Republic
74% AI deal score
$1,494
$1,333
Save $161
From ORD
Elite
Jul 18
Punta Cana, Dominican Republic
74% AI deal score
$1,493
$1,333
Save $160
From ORD
Elite
Sep 27
Punta Cana, Dominican Republic
74% AI deal score
$1,545
$1,336
Save $209
From ORD
Elite
Nov 14
Punta Cana, Dominican Republic
74% AI deal score
$1,488
$1,336
Save $152
From ORD
Elite
Nov 13
Punta Cana, Dominican Republic
74% AI deal score
$1,493
$1,347
Save $146
From ORD
Elite
Oct 03
Punta Cana, Dominican Republic
74% AI deal score
$1,545
$1,360
Save $185
From ORD
Elite
Sep 26
Punta Cana, Dominican Republic
74% AI deal score
$1,545
$1,360
Save $185
From ORD
Elite
Nov 13
Punta Cana, Dominican Republic
74% AI deal score
$1,521
$1,360
Save $161
From ORD
Elite
Nov 29
Punta Cana, Dominican Republic
73% AI deal score
$1,448
$1,323
Save $125
From ORD
Elite
Nov 30
Punta Cana, Dominican Republic
73% AI deal score
$1,433
$1,323
Save $110
From ORD
Elite
Nov 30
Punta Cana, Dominican Republic
73% AI deal score
$1,443
$1,333
Save $110
From ORD
Elite
Jul 10
Punta Cana, Dominican Republic
73% AI deal score
$1,480
$1,333
Save $147
From ORD
Elite
Jul 17
Punta Cana, Dominican Republic
73% AI deal score
$1,478
$1,333
Save $145
From ORD
Elite
Jul 21
Punta Cana, Dominican Republic
73% AI deal score
$1,478
$1,333
Save $145
From ORD
Elite
Nov 14
Punta Cana, Dominican Republic
73% AI deal score
$1,466
$1,336
Save $130
From ORD
Elite
Nov 28
Punta Cana, Dominican Republic
73% AI deal score
$1,450
$1,350
Save $100
From ORD
Elite
Nov 07
Punta Cana, Dominican Republic
73% AI deal score
$1,479
$1,350
Save $129
From ORD
Elite
Nov 07
Punta Cana, Dominican Republic
73% AI deal score
$1,479
$1,357
Save $122
From ORD
Elite
Nov 14
Punta Cana, Dominican Republic
71% AI deal score
$1,467
$1,445
Save $22
From ORD
Elite
Oct 25
Punta Cana, Dominican Republic
71% AI deal score
$1,771
$1,758
Save $13
From ORD
Elite
Oct 25
Punta Cana, Dominican Republic
71% AI deal score
$1,818
$1,758
Save $60
From ORD
Elite
Oct 19
Punta Cana, Dominican Republic
71% AI deal score
$1,758
From ORD
Elite
Oct 19
Punta Cana, Dominican Republic
71% AI deal score
$1,762
$1,758
Save $4
From ORD
Elite
Oct 04
Punta Cana, Dominican Republic
71% AI deal score
$1,765
$1,758
Save $7
From ORD
Elite
Oct 08
Punta Cana, Dominican Republic
71% AI deal score
$1,764
$1,758
Save $6
From ORD
Elite
Aug 29
Punta Cana, Dominican Republic
71% AI deal score
$1,812
$1,758
Save $54
From ORD
Elite
Aug 26
Punta Cana, Dominican Republic
71% AI deal score
$1,814
$1,758
Save $56
From ORD
Elite
Oct 08
Punta Cana, Dominican Republic
71% AI deal score
$1,758
From ORD
Elite
Oct 04
Punta Cana, Dominican Republic
71% AI deal score
$1,758
From ORD
Elite
Oct 25
Punta Cana, Dominican Republic
71% AI deal score
$1,783
$1,764
Save $19
From ORD
Elite
Oct 25
Punta Cana, Dominican Republic
71% AI deal score
$1,771
$1,764
Save $7
From ORD
Elite
Oct 25
Punta Cana, Dominican Republic
71% AI deal score
$1,771
$1,764
Save $7
From ORD
Elite
Oct 07
Punta Cana, Dominican Republic
71% AI deal score
$1,764
From ORD
Elite
Oct 08
Punta Cana, Dominican Republic
71% AI deal score
$1,764
From ORD
Elite
Oct 04
Punta Cana, Dominican Republic
71% AI deal score
$1,765
$1,764
Save $1
From ORD
Elite
Nov 03
Punta Cana, Dominican Republic
70% AI deal score
$1,506
From ORD
Elite
Sep 08
Punta Cana, Dominican Republic
70% AI deal score
$1,758
From ORD
Elite
Sep 09
Punta Cana, Dominican Republic
70% AI deal score
$1,758
From ORD
Elite
Sep 26
Punta Cana, Dominican Republic
70% AI deal score
$1,758
From ORD
Elite
Sep 20
Punta Cana, Dominican Republic
70% AI deal score
$1,758
From ORD
Elite
Sep 06
Punta Cana, Dominican Republic
70% AI deal score
$1,758
From ORD
Elite
Sep 28
Punta Cana, Dominican Republic
70% AI deal score
$1,764
From ORD
Elite
Sep 29
Punta Cana, Dominican Republic
70% AI deal score
$1,764