Cheap flights from Puerto Rico to Chicago from $49

Round-trip
1 adult
Economy
From?
To?
Mon 11/1
Mon 11/8

Travel Restriction Alert

The COVID-19 (coronavirus) outbreak may impact travel from Puerto Rico to Chicago.
View current United States travel restrictions

Flight information for Puerto Rico to Chicago

Find info about flight duration, direct flights, and airports for your flight from Puerto Rico to Chicago
Best Price Found$97The best flight deal from Puerto Rico to Chicago found on momondo in the last 72 hours is $97
Fastest flight time5h 13mThe fastest flight from Puerto Rico to Chicago takes 5h 13m
Direct flightsMon, Sat and SunDirect flights go from Puerto Rico to Chicago on Monday, Saturday and Sunday. Airlines offering direct flights are: Air Canada and American Airlines.
Airports in Chicago3 airportsThere are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Puerto Rico to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies to Chicago from Puerto Rico?

Frontier

American Airlines, Delta, and Frontier are the most popular carriers operating from Puerto Rico to Chicago

What is the cheapest Puerto Rico to Chicago flight route?

San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl

Fly from San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl for the best Puerto Rico - Chicago flight prices


Easily compare round-trip flights from Puerto Rico to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Puerto Rico to Chicago by changing tabs
Frontier
Nov 9
SJU12:09 pmSan Juan Luis Munoz Marin Intl
9h 00m
1 stop
ORD9:09 pmChicago O'Hare Intl
Nov 13
ORD8:57 amChicago O'Hare Intl
8h 02m
1 stop
SJU4:59 pmSan Juan Luis Munoz Marin Intl
Multiple Airlines
Nov 6
SJU2:30 pmSan Juan Luis Munoz Marin Intl
6h 33m
1 stop
ORD9:03 pmChicago O'Hare Intl
Nov 10
ORD1:12 amChicago O'Hare Intl
9h 12m
1 stop
SJU10:24 amSan Juan Luis Munoz Marin Intl
Spirit Airlines
Jan 12
SJU11:40 pmSan Juan Luis Munoz Marin Intl
7h 28m
1 stop
ORD7:08 amChicago O'Hare Intl
Jan 13
ORD12:43 pmChicago O'Hare Intl
7h 20m
1 stop
SJU8:03 pmSan Juan Luis Munoz Marin Intl
Frontier
Nov 8
SJU10:58 pmSan Juan Luis Munoz Marin Intl
18h 27m
1 stop
ORD5:25 pmChicago O'Hare Intl
Nov 13
ORD8:57 amChicago O'Hare Intl
8h 02m
1 stop
SJU4:59 pmSan Juan Luis Munoz Marin Intl
Multiple Airlines
Feb 4
SJU10:59 pmSan Juan Luis Munoz Marin Intl
22h 25m
1 stop
ORD9:24 pmChicago O'Hare Intl
Feb 8
ORD12:15 amChicago O'Hare Intl
9h 14m
1 stop
SJU9:29 amSan Juan Luis Munoz Marin Intl
Delta
Dec 1
SJU1:33 pmSan Juan Luis Munoz Marin Intl
7h 15m
1 stop
MDW8:48 pmChicago Midway
Dec 7
MDW7:53 amChicago Midway
8h 03m
1 stop
SJU3:56 pmSan Juan Luis Munoz Marin Intl

Find the cheapest one-way flights from Puerto Rico to Chicago

If you're looking for one-way flights from Puerto Rico to Chicago, view some of our deals below provided by Frontier and Spirit Airlines
Frontier
Nov 13
SJU1:19 pmSan Juan Luis Munoz Marin Intl
7h 50m
1 stop
ORD9:09 pmChicago O'Hare Intl
Spirit Airlines
Nov 2
SJU4:52 amSan Juan Luis Munoz Marin Intl
12h 01m
1 stop
ORD4:53 pmChicago O'Hare Intl
Multiple Airlines
Nov 30
SJU10:24 pmSan Juan Luis Munoz Marin Intl
23h 06m
1 stop
ORD9:30 pmChicago O'Hare Intl

Search last-minute flights to Chicago from Puerto Rico

Find and compare flight prices for your last-minute flight from Puerto Rico to Chicago
Multiple Airlines
Nov 2
SJU4:52 amSan Juan Luis Munoz Marin Intl
9h 46m
1 stop
ORD2:38 pmChicago O'Hare Intl
Nov 17
ORD1:12 amChicago O'Hare Intl
15h 47m
1 stop
SJU4:59 pmSan Juan Luis Munoz Marin Intl
Spirit Airlines
Nov 3
BQN11:30 pmAguadilla Borinquen
7h 08m
1 stop
ORD6:38 amChicago O'Hare Intl
Nov 6
ORD3:10 pmChicago O'Hare Intl
6h 10m
1 stop
BQN9:20 pmAguadilla Borinquen
Frontier
Nov 6
SJU1:19 pmSan Juan Luis Munoz Marin Intl
7h 50m
1 stop
ORD9:09 pmChicago O'Hare Intl
Nov 10
ORD1:12 amChicago O'Hare Intl
18h 46m
1 stop
SJU7:58 pmSan Juan Luis Munoz Marin Intl
Multiple Airlines
Nov 6
SJU2:30 pmSan Juan Luis Munoz Marin Intl
6h 33m
1 stop
ORD9:03 pmChicago O'Hare Intl
Nov 10
ORD1:12 amChicago O'Hare Intl
9h 12m
1 stop
SJU10:24 amSan Juan Luis Munoz Marin Intl
Spirit Airlines
Nov 4
BQN11:30 pmAguadilla Borinquen
7h 08m
1 stop
ORD6:38 amChicago O'Hare Intl
Nov 8
ORD2:10 pmChicago O'Hare Intl
6h 19m
1 stop
BQN8:29 pmAguadilla Borinquen
Multiple Airlines
Nov 2
SJU2:30 pmSan Juan Luis Munoz Marin Intl
6h 33m
1 stop
ORD9:03 pmChicago O'Hare Intl
Nov 9
ORD8:32 amChicago O'Hare Intl
8h 27m
1 stop
SJU4:59 pmSan Juan Luis Munoz Marin Intl

Best airlines flying from Puerto Rico to Chicago

Compare and see reviews for airlines that fly from Puerto Rico to Chicago with momondo
AirlineRatingFree CancellationPrice
Frontier
PriceFrom $85
Free Cancellation
Rating
6.2
6.6

Boarding

5.9

Comfort

7.0

Crew

4.8

Entertainment

5.0

Food

Reviews

Three gate changes three flight time changes extra charges for everything. This is the first and last time I will fly this airline.

1 / 10
Spirit Airlines
PriceFrom $118
Free Cancellation
Rating
6.4
6.5

Boarding

6.0

Comfort

6.9

Crew

4.9

Entertainment

5.3

Food

Reviews

This is the first flight landing and take off with Spirit that was smooth. The pilot has my congratulations.

1 / 10
Delta
PriceFrom $164
Free Cancellation
Rating
8.2
8.2

Boarding

8.4

Comfort

8.3

Crew

8.1

Entertainment

8.0

Food

Reviews

Great

1 / 10
JetBlue
PriceFrom $174
Free Cancellation
Rating
7.0
7.3

Boarding

7.6

Comfort

7.9

Crew

7.2

Entertainment

6.8

Food

Reviews

The boarding was late and when I arrived at my final destination I had to wait some more to exit the plane .. about 20 mins

1 / 10
American Airlines
PriceFrom $182
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.8

Crew

7.1

Entertainment

6.8

Food

Reviews

Flight attendant for first class is definitely not a morning person. Oh and the WiFi DID NOT WORK!

1 / 10
United Airlines
PriceFrom $183
Free Cancellation
Rating
6.9
7.3

Boarding

6.7

Comfort

7.5

Crew

6.7

Entertainment

6.2

Food

Reviews

Seats were very small. The plane felt very cramped. Lots of turbulence. Horrible flight

1 / 10

  • Are airlines flying from Puerto Rico to Chicago offering flexible cancellation due to COVID-19?

    To ease the stress of booking flights, some of our airline partners flying from Puerto Rico to Chicago are responding to the global pandemic. The following airlines may have a flexible cancellation policy to help accommodate travelers: United Airlines, Spirit Airlines, and American Airlines.


Can I fly to Chicago from Puerto Rico right now?

Information is based on travel restrictions from Puerto Rico to Chicago

Most visitors from Puerto Rico need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Puerto Rico must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Puerto Rico are not required to quarantine after entering Chicago.

Can I fly back to Puerto Rico from Chicago?

Returning to Puerto Rico from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Puerto Rico.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Puerto Rico.

If you are planning to travel to Chicago at this time, it is recommended that you stay up to date on current restrictions and follow proper safety measures while in public.

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