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Cheap flights from Roswell, New Mexico to Chicago from $358

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Roswell, New Mexico to Chicago departing on 5/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Roswell, New Mexico to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
12:30 pm - 9:14 pm
ROW
-
ORD
7h 44m
1 stop
American Airlines Logo
7:02 am - 11:24 am
ORD
-
ROW
5h 22m
1 stop
$358American Airlines
Tue, May 19 - Sat, May 23
United Airlines Logo
5:58 pm - 12:44 am
ROW
-
ORD
5h 46m
1 stop
United Airlines Logo
5:00 am - 10:01 am
ORD
-
ROW
6h 01m
1 stop
$370United Airlines
Fri, May 22 - Tue, May 26
United Airlines Logo
5:58 pm - 6:51 pm
ROW
-
ORD
23h 53m
1 stop
United Airlines Logo
5:00 am - 10:01 am
ORD
-
ROW
6h 01m
1 stop
$458United Airlines
Mon, Jun 1 - Sun, Jun 7
United Airlines Logo
5:58 pm - 12:44 am
ROW
-
ORD
5h 46m
1 stop
United Airlines Logo
6:00 am - 10:01 am
ORD
-
ROW
5h 01m
1 stop
$504United Airlines
Thu, May 21 - Mon, May 25
United Airlines Logo
5:53 pm - 12:58 am
ROW
-
ORD
6h 05m
1 stop
United Airlines Logo
7:45 pm - 10:01 am
ORD
-
ROW
15h 16m
2 stops
$558United Airlines
Wed, May 20 - Sun, May 24
United Airlines Logo
5:58 pm - 1:15 pm
ROW
-
ORD
18h 17m
2 stops
United Airlines Logo
5:00 am - 10:01 am
ORD
-
ROW
6h 01m
1 stop
$561United Airlines
Mon, Jun 1 - Sun, Jun 7
United Airlines Logo
5:53 pm - 12:58 am
ROW
-
ORD
6h 05m
1 stop
United Airlines Logo
9:34 pm - 5:23 pm
ORD
-
ROW
20h 49m
2 stops
$597United Airlines
Tue, May 19 - Sat, May 23
United Airlines Logo
5:58 pm - 12:45 am
ROW
-
ORD
29h 47m
2 stops
United Airlines Logo
5:00 am - 10:01 am
ORD
-
ROW
6h 01m
1 stop
$610United Airlines
Fri, May 22 - Tue, May 26
United Airlines Logo
5:58 pm - 9:45 am
ROW
-
ORD
14h 47m
2 stops
United Airlines Logo
5:00 am - 10:01 am
ORD
-
ROW
6h 01m
1 stop
$624United Airlines
Thu, May 21 - Mon, May 25
United Airlines Logo
5:58 pm - 7:57 am
ROW
-
ORD
12h 59m
2 stops
United Airlines Logo
7:05 am - 5:23 pm
ORD
-
ROW
11h 18m
2 stops
$958United Airlines
Fri, May 22 - Tue, May 26

United Airlines flights from Roswell, New Mexico to Chicago

Our best United Airlines deals on Roswell, New Mexico to Chicago flight tickets
United Airlines
May 22
ROW5:58 pmRoswell Intl
5h 46m
1 stop
ORD12:44 amChicago O'Hare Intl
May 26
ORD5:00 amChicago O'Hare Intl
6h 01m
1 stop
ROW10:01 amRoswell Intl
$370
United Airlines
Jun 1
ROW5:58 pmRoswell Intl
23h 53m
1 stop
ORD6:51 pmChicago O'Hare Intl
Jun 7
ORD5:00 amChicago O'Hare Intl
6h 01m
1 stop
ROW10:01 amRoswell Intl
$458
United Airlines
May 21
ROW5:58 pmRoswell Intl
5h 46m
1 stop
ORD12:44 amChicago O'Hare Intl
May 25
ORD6:00 amChicago O'Hare Intl
5h 01m
1 stop
ROW10:01 amRoswell Intl
$504

American Airlines flights from Roswell, New Mexico to Chicago

Our best American Airlines deals on Roswell, New Mexico to Chicago flight tickets
American Airlines
May 19
ROW12:30 pmRoswell Intl
7h 44m
1 stop
ORD9:14 pmChicago O'Hare Intl
May 23
ORD7:02 amChicago O'Hare Intl
5h 22m
1 stop
ROW11:24 amRoswell Intl
$358
American Airlines
May 20
ROW12:30 pmRoswell Intl
8h 03m
2 stops
ORD9:33 pmChicago O'Hare Intl
May 24
ORD2:55 pmChicago O'Hare Intl
8h 11m
2 stops
ROW10:06 pmRoswell Intl
$1,009
American Airlines
May 11
ROW12:30 pmRoswell Intl
8h 20m
2 stops
ORD9:50 pmChicago O'Hare Intl
May 14
ORD1:29 pmChicago O'Hare Intl
9h 30m
2 stops
ROW9:59 pmRoswell Intl
$1,291

momondo Fare Finder

 
Customize your flight search to find flights from Roswell, New Mexico to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 7, 2026.
Use the filters below to find and compare flights from Roswell, New Mexico to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RoswellChicago

ROW - ORD

ROWORD

Roswell Intl

Tue 5/19

12:30 pm-9:14 pm

1 stop7h 44m

Chicago O'Hare Intl

Sat 5/23

7:02 am-11:24 am

1 stop5h 22m

$358

RoswellChicago

ROW - ORD

ROWORD

Roswell Intl

Fri 5/22

5:58 pm-12:44 am

1 stop5h 46m

Chicago O'Hare Intl

Tue 5/26

5:00 am-10:01 am

1 stop6h 01m

$370

RoswellChicago

ROW - ORD

ROWORD

Roswell Intl

Mon 6/1

5:58 pm-6:51 pm

1 stop23h 53m

Chicago O'Hare Intl

Sun 6/7

5:00 am-10:01 am

1 stop6h 01m

$458
Quickest round-trip

RoswellChicago

ROW - ORD

ROWORD

Roswell Intl

Thu 5/21

5:58 pm-12:44 am

1 stop5h 46m

Chicago O'Hare Intl

Mon 5/25

6:00 am-10:01 am

1 stop5h 01m

$504

RoswellChicago

ROW - ORD

ROWORD

Roswell Intl

Wed 5/20

5:53 pm-12:58 am

1 stop6h 05m

Chicago O'Hare Intl

Sun 5/24

7:45 pm-10:01 am

2 stops15h 16m

$558

RoswellChicago

ROW - ORD

ROWORD

Roswell Intl

Mon 6/1

5:58 pm-1:15 pm

2 stops18h 17m

Chicago O'Hare Intl

Sun 6/7

5:00 am-10:01 am

1 stop6h 01m

$561

RoswellChicago

ROW - ORD

ROWORD

Roswell Intl

Tue 5/19

5:53 pm-12:58 am

1 stop6h 05m

Chicago O'Hare Intl

Sat 5/23

9:34 pm-5:23 pm

2 stops20h 49m

$597

RoswellChicago

ROW - ORD

ROWORD

Roswell Intl

Fri 5/22

5:58 pm-12:45 am

2 stops29h 47m

Chicago O'Hare Intl

Tue 5/26

5:00 am-10:01 am

1 stop6h 01m

$610

RoswellChicago

ROW - ORD

ROWORD

Roswell Intl

Thu 5/21

5:58 pm-9:45 am

2 stops14h 47m

Chicago O'Hare Intl

Mon 5/25

5:00 am-10:01 am

1 stop6h 01m

$624

RoswellChicago

ROW - ORD

ROWORD

Roswell Intl

Fri 5/22

5:58 pm-7:57 am

2 stops12h 59m

Chicago O'Hare Intl

Tue 5/26

7:05 am-5:23 pm

2 stops11h 18m

$958

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

When to book flights from Roswell, New Mexico to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Roswell, New Mexico to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Roswell, New Mexico to Chicago (ROW to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Roswell, New Mexico to Chicago

Fastest flight time

5h 46m

Direct flights

None
The fastest flight from Roswell, New Mexico to Chicago takes 5h 46m
There are no direct flights from Roswell, New Mexico to Chicago. There are no popular flight routes from Roswell, New Mexico to Chicago.
Search flight deals

Frequently asked questions about flying from Roswell, New Mexico to Chicago

  • How far is Roswell Intl to Chicago by plane?

    A flight from Roswell Intl to Chicago will travel around 1090.7 mi. In terms of flight time, this usually takes a little over 5h 46m.

  • When did momondo last update prices for flights from Roswell Intl Airport to Chicago?

    Prices for flights from Roswell Intl Airport to Chicago are updated daily.

  • How old do you have to be to fly from Roswell Intl Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Roswell Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Roswell, New Mexico to Chicago?

Frequently asked questions about flying from Roswell, New Mexico to Chicago

  • How do I get Price Alerts for flights from Roswell, New Mexico to Chicago?

    Search flight deals from Roswell, New Mexico to Chicago. While viewing offers you’ll have the option to create a Price Alert.

  • How can I save money on flights from Roswell, New Mexico to Chicago with momondo?

    By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Roswell to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Roswell.

Can I find flights from Roswell to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Roswell which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Roswell to Chicago?

momondo helps you find the best flight between Roswell and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Roswell to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Roswell to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport