Cheap flights from Chicago to Punta Cana from $743 MDW, ORD, RFD → PUJ
Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD) → Punta Cana International Airport (PUJ)
The cheapest return found recently is $743 with Frontier Airlines, 15 Dec – 6 Jan 2027, found 2 days ago.
- Cheapest return found recently
- $743, 15 Dec to 6 Jan 2027
- Usual return price
- $486 to $704
- Cheapest month to fly
- January 2027, return fares from $376 found in the last 7 days
- Airlines with nonstop flights
- American Airlines, United Airlines, Arajet
Return
The cheapest return fare on each of 7 departure dates is usually $486 to $704.
Cheapest return found recently
$743
15 Dec – 6 Jan 2027 · Frontier Airlines
O'Hare International Airport (ORD) → Punta Cana International Airport (PUJ)
Leaves 5:24 p.m. · Return leaves 11:45 p.m. · 52 h 19 min of travel, both ways together
out 2 stops, back 2 stops · via Orlando International Airport (MCO), Luis Munoz Marin International Airport (SJU), Cleveland Hopkins International Airport (CLE), Hartsfield-Jackson Atlanta International Airport (ATL) · overnight connection · 21 h connection
found 2 days ago
Cheapest nonstop return
$1,115
15 Dec – 5 Jan 2027 · United Airlines
O'Hare International Airport (ORD) → Punta Cana International Airport (PUJ)
Leaves 9:17 a.m. · Return leaves 9:41 p.m. · 9 h 56 min of travel, both ways together
out nonstop, back nonstop
found 2 days ago
Found recently, and the cheapest we hold
$743 15 Dec – 6 Jan 2027found 2 days agoSee prices for these dates
$376 8 Jan 2027 – 16 Jan 2027found 7 days agoSee prices for these dates
What have prices looked like?
Over 49 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $372 to $631.
At $743, the cheapest return found recently is above that range.
Those were the prices on those days, not today's.
Is this a good return price?
Compared with the cheapest return fare on each of 7 departure dates from 16 Nov to 8 Jan 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other 22-night return fares leaving within 3 days of 15 Dec to compare.
Every date we hold
89 fares on 7 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 16 Nov – 23 Nov | $438 | American Airlines | O'Hare International Airport (ORD) → Punta Cana International Airport (PUJ) | out 1 stop, back nonstop | found 7 days ago | See prices for these dates |
| 15 Dec – 6 Jan 2027 | $743 | Frontier Airlines | O'Hare International Airport (ORD) → Punta Cana International Airport (PUJ) | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| 22 Dec – 30 Dec | $664 | American Airlines | O'Hare International Airport (ORD) → Punta Cana International Airport (PUJ) | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| 27 Dec – 1 Jan 2027 | $862 | Frontier Airlines | O'Hare International Airport (ORD) → Punta Cana International Airport (PUJ) | out 2 stops, back nonstop | found 7 days ago | See prices for these dates |
| 1 Jan 2027 – 8 Jan 2027 | $535 | Arajet | O'Hare International Airport (ORD) → Punta Cana International Airport (PUJ) | out nonstop, back 1 stop | found 7 days ago | See prices for these dates |
| 3 Jan 2027 – 10 Jan 2027 | $567 | jetBlue | O'Hare International Airport (ORD) → Punta Cana International Airport (PUJ) | out 1 stop, back 1 stop | found 7 days ago | See prices for these dates |
| 8 Jan 2027 – 16 Jan 2027 | $376 | Arajet | O'Hare International Airport (ORD) → Punta Cana International Airport (PUJ) | out nonstop, back nonstop | found 7 days ago | See prices for these dates |
Which month looks cheapest?
January 2027 is the cheapest month — from $376.
Airlines on the cheapest dates: American Airlines, Frontier Airlines, Arajet, jetBlue.
Premium cabin fares from Chicago to Punta Cana
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 15 Dec – 6 Jan 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Chicago to Punta Cana?
Return
Fares 14 to 29 days before departure were typically 20% lower than 0 to 6 days before departure.
From the cheapest return each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $480 | $417 | +26% | 9 |
| 7–13 days | $417 | $415 | +9% | 15 |
| 14–29 days | $382 | $372 | Cheapest seen | 32 |
| 30–59 days | $460 | $372 | +20% | 35 |
| 60–89 days | $579 | $376 | +52% | 32 |
| 90–179 days | $446 | $401 | +17% | 24 |
Live price for these dates
The cheapest return found recently is for 15 Dec – 6 Jan 2027. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a return flight from Chicago to Punta Cana?
The cheapest return found recently is $743 with Frontier Airlines, 15 Dec to 6 Jan 2027, found 2 days ago. The cheapest return we hold, of any age, is $376 with Arajet, 8 Jan 2027 to 16 Jan 2027, found 7 days ago. The cheapest return fare on each of 7 departure dates is usually $486 to $704.
What is the cheapest month to fly from Chicago to Punta Cana?
January 2027 is the cheapest month for a return, from $376, 8 Jan 2027 to 16 Jan 2027, found 7 days ago.
How far ahead should I book a flight from Chicago to Punta Cana?
In 49 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 20% lower than 0 to 6 days before departure.
Is there a direct flight from Chicago to Punta Cana?
Yes, the cheapest nonstop return found recently is $1,115 with United Airlines, 15 Dec to 5 Jan 2027, found 2 days ago.
Which airlines have the cheapest flights from Chicago to Punta Cana?
Between 16 Nov and 8 Jan 2027, American Airlines has the cheapest return on 2 of the 7 departure dates we hold, Frontier Airlines on 2 and Arajet on 2.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work