Cheap flights from RSW to ORD (Southwest Florida Intl. to O'Hare Intl.)

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Cheap Flights from RSW to ORD starting at $66 One Way, $140 Round Trip

Prices starting at $140 for return flights and $66 for one-way flights to O'Hare Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Dec 3 - Sun, Dec 6
RSW
Fort Myers
ORD
Chicago
$140 Roundtrip, found 6 hours ago
$140
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Fort Myers to Chicago, returning Sun, Dec 6, priced at $140 found 6 hours ago
Thu, Dec 3 - Mon, Dec 7
RSW
Fort Myers
ORD
Chicago
$142 Roundtrip, found 7 hours ago
$142
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Fort Myers to Chicago, returning Mon, Dec 7, priced at $142 found 7 hours ago
Tue, Nov 24 - Mon, Nov 30
RSW
Fort Myers
ORD
Chicago
$148 Roundtrip, found 2 hours ago
$148
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Nov 24 from Fort Myers to Chicago, returning Mon, Nov 30, priced at $148 found 2 hours ago
Tue, Nov 24 - Mon, Nov 30
RSW
Fort Myers
ORD
Chicago
$160 Roundtrip, found 2 hours ago
$160
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Nov 24 from Fort Myers to Chicago, returning Mon, Nov 30, priced at $160 found 2 hours ago
Wed, Jan 20 - Sat, Jan 23
RSW
Fort Myers
ORD
Chicago
$231 Roundtrip, just found
$231
Roundtrip
just found
Select United flight, departing Wed, Jan 20 from Fort Myers to Chicago, returning Sat, Jan 23, priced at $231 just found

Hotel Ideas near O'Hare Intl.

Airport Hotels near O'Hare Intl.

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$227 nightly
The price is $266 total per night from Nov 13 to Nov 14
$266 total
Nov 13 - Nov 14
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.6/10 Excellent! (2,563 reviews)
"Convenience is the only reason to stay here. My shower did not work for some reason. It is a tired property but incredibly convenient."

Reviewed on Oct 21, 2026

Hilton Chicago O'Hare Airport
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd Rosemont IL
$144 nightly
The price is $164 total per night from Nov 1 to Nov 2
$164 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (2,874 reviews)
"A more run down than I expected but a great location and price."

Reviewed on Oct 21, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$161 nightly
The price is $183 total per night from Oct 24 to Oct 25
$183 total
Oct 24 - Oct 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
9/10 Wonderful! (3,285 reviews)
"I realky enjoyed my stay. The hotel was easy navigating to the CTA was super easy . The room itself was clean and quiet . I have no cons really. I thought staying by the airport was going to give lackluster but it did not . I’m very happy with my choice and would definitely stay again . Hopefully ..."

Reviewed on Oct 21, 2026

Hyatt Regency O'Hare Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$107 nightly
The price is $127 total per night from Nov 11 to Nov 12
$127 total
Nov 11 - Nov 12
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$116 nightly
The price is $138 total per night from Oct 22 to Oct 23
$138 total
Oct 22 - Oct 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,550 reviews)
"Probably one if the worst places ive stayed on Hotels.com. Overall, the hotel is fine, however the pictures look and feel quite different than what the rooms actually felt like. The rooms just felt old and dirty with carpeted floors and stains. Not amenities in the rooms and the front desk wasn’t ..."

Reviewed on Oct 21, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$152 nightly
The price is $181 total per night from Nov 1 to Nov 2
$181 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chicago Hotels With Airport Transportation

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave Elk Grove Village IL
$60 nightly
The price is $68 total per night from Oct 26 to Oct 27
$68 total
Oct 26 - Oct 27
Total with taxes and fees
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (2,012 reviews)
"El lugar muy limpio. Y accesible a todo"

Reviewed on Oct 21, 2026

Motel 6 Elk Grove Village, IL - O'Hare
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
777 E Grand Avenue Bensenville IL
$106 nightly
The price is $117 total per night from Oct 28 to Oct 29
$117 total
Oct 28 - Oct 29
Total with taxes and fees
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
$101 nightly
The price is $116 total per night from Nov 11 to Nov 12
$116 total
Nov 11 - Nov 12
Total with taxes and fees
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Comfort Suites Chicago O'Hare Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Chicago Hotels

Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
The price is $183 total per night from Nov 3 to Nov 4
$183 total
per night
Nov 3 - Nov 4
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
The price is $141 total per night from Nov 12 to Nov 13
$141 total
per night
Nov 12 - Nov 13
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave Elk Grove Village IL
The price is $68 total per night from Oct 26 to Oct 27
$68 total
per night
Oct 26 - Oct 27
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (2,012 reviews)
"El lugar muy limpio. Y accesible a todo"

Reviewed on Oct 21, 2026

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
511 North Columbus Drive Chicago IL
$180 nightly
The price is $241 total per night from Nov 10 to Nov 11
$241 total
Nov 10 - Nov 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
$215 nightly
The price is $256 total per night from Oct 31 to Nov 1
$256 total
Oct 31 - Nov 1
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,719 reviews)
"The rooms are very dated, with wall paper peeling up in areas, sheets are thin and had some stains as well."

Reviewed on Oct 21, 2026

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
$152 nightly
The price is $181 total per night from Nov 1 to Nov 2
$181 total
Nov 1 - Nov 2
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,973 reviews)
"Ubicación"

Reviewed on Oct 20, 2026

Embassy Suites by Hilton Chicago Downtown River North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

RSW to ORD Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
RSW Address & GPS
Address:
11000 Terminal Access Road
Fort Myers FL,
United States
IATA Code:
RSW
Longitude:
-81.755263
Latitude:
26.527887
Time Zone:
America/New_York
ORD Address & GPS
Address:
10000 West O'Hare
Chicago IL, 60666
United States
IATA Code:
ORD
Longitude:
-87.904876
Latitude:
41.976912
Time Zone:
America/Chicago

Frequently asked questions

Are there non-stop flights from Southwest Florida Intl. Airport to ORD?
You can jet directly from RSW to ORD, so there's no need to waste your valuable PTO days sitting around waiting for your connecting flight. Enjoy a worry-free journey aboard one of the 4 air carriers with nonstop services on this route. Popular choices include:

  • United Airlines
  • American Airlines
  • Spirit Airlines
  • Frontier Airlines

What is the shortest flight from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
Make the most of the opportunity to sit back and relax on your trip from Fort Myers to Chicago. The shortest flight time from Southwest Florida Intl. Airport (RSW) to O'Hare Airport is 3 hours and 5 minutes, which gives you plenty of time to enjoy a wine or get absorbed in a good movie.
How many hours flight from Southwest Florida Intl. Airport (RSW) to ORD?
The trip from RSW to ORD will take roughly 3 hours and 13 minutes. A few TV shows, some light reading and a long nap will help make time fly.
What airlines have the most flights from RSW to O'Hare Intl. Airport (ORD)?
Few things are as fun as zipping up your bags and jumping on a plane somewhere exciting. Satisfy your wanderlust and fly from Fort Myers to Chicago with one of these leading airlines:

  • Frontier Airlines - (F9) with 13 flights every month
  • Spirit Airlines - (NK) with 47 flights every month
  • American Airlines - (AA) with 119 flights every month
  • United Airlines - (UA) with 158 flights every month

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

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