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 $44 One Way, $88 Round Trip

Prices starting at $88 for return flights and $44 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, Apr 16 - Sun, Apr 19
RSW
Fort Myers
ORD
Chicago
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Apr 16 from Fort Myers to Chicago, returning Sun, Apr 19, priced at $88 just found
Thu, Apr 16 - Sun, Apr 19
RSW
Fort Myers
ORD
Chicago
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Apr 16 from Fort Myers to Chicago, returning Sun, Apr 19, priced at $88 just found
Thu, Apr 23 - Mon, Apr 27
RSW
Fort Myers
ORD
Chicago
$112 Roundtrip, found 5 hours ago
$112
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Thu, Apr 23 from Fort Myers to Chicago, returning Mon, Apr 27, priced at $112 found 5 hours ago
Wed, Apr 29 - Thu, May 7
RSW
Fort Myers
ORD
Chicago
$288 Roundtrip, found 3 days ago
$288
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Apr 29 from Fort Myers to Chicago, returning Thu, May 7, priced at $288 found 3 days ago
Thu, Jun 11 - Mon, Jun 15
RSW
Fort Myers
ORD
Chicago
$295 Roundtrip, just found
$295
Roundtrip
just found
Select United flight, departing Thu, Jun 11 from Fort Myers to Chicago, returning Mon, Jun 15, priced at $295 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
$221 nightly
The price is $259 total per night from May 2 to May 3
$259 total
May 2 - May 3
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 ...
8.4/10 Very Good! (2,245 reviews)
Old, dirty carpet. Fine bed. Clean sheets nothing special.

Reviewed on Apr 1, 2026

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$135 nightly
The price is $154 total per night from Apr 4 to Apr 5
$154 total
Apr 4 - Apr 5
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 ...
8.8/10 Excellent! (2,448 reviews)
Very friendly and helpful staff. Room was very clean and comfortable.

Reviewed on Apr 2, 2026

Hyatt Regency O'Hare Chicago
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
6600 Mannheim Road, building 2 Rosemont IL
$104 nightly
The price is $118 total per night from Apr 6 to Apr 7
$118 total
Apr 6 - Apr 7
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 breakfast ...
9/10 Wonderful! (2,888 reviews)
Clean rooms, great staff, no complaints. And any issues that's I have had were addressed right away and/or I received parking or room comps. I have stayed here several times with my family which includes small children. Great property and will always stay when coming into the Chicago area

Reviewed on Apr 1, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG
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
$110 nightly
The price is $129 total per night from Apr 5 to Apr 6
$129 total
Apr 5 - Apr 6
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 ...
8/10 Very Good! (10,005 reviews)
We were so thankful for the bellman on duty Saturday morning who was very helpful in explaining get a bus card and what bus lines to look for. Our first night we had dinner in Raphael’s and the French Onion soup was delicious. The room was really hot when we arrived and we had to open the windows ...

Reviewed on Apr 2, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$119 nightly
The price is $140 total per night from Apr 8 to Apr 9
$140 total
Apr 8 - Apr 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (4,036 reviews)
The hotel was fine as it is, the restaurant in the lobby w welcome addition at a good price point for families

Reviewed on Apr 2, 2026

Hilton Chicago/Magnificent Mile Suites
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
$127 nightly
The price is $149 total per night from Apr 12 to Apr 13
$149 total
Apr 12 - Apr 13
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! (5,806 reviews)
Overall nice hotel great service

Reviewed on Apr 2, 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.

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
$55 nightly
The price is $62 total per night from Apr 26 to Apr 27
$62 total
Apr 26 - Apr 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! (1,898 reviews)
Good enough for cheap price

Reviewed on Apr 1, 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
$95 nightly
The price is $106 total per night from Apr 23 to Apr 24
$106 total
Apr 23 - Apr 24
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 ...
7.4/10 Good! (1,330 reviews)
Breakfast was good, delicious waffles and coffee. The pool was way too hot, dirty and no towels. The kids didn’t want to play longer than 20 minutes in the pool. The room was ok, the air conditioner was very loud. We got locked out of our room at 9am the day of checkout. The elevator broke down. ...

Reviewed on Apr 2, 2026

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
$70 nightly
The price is $80 total per night from Apr 8 to Apr 9
$80 total
Apr 8 - Apr 9
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 ...
8/10 Very Good! (2,924 reviews)
Airport shuttle was easy.

Reviewed on Apr 2, 2026

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
$79 nightly
The price is $93 total per night from Apr 14 to Apr 15
$93 total
Apr 14 - Apr 15
Total with taxes and fees
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
$110 nightly
The price is $129 total per night from Apr 5 to Apr 6
$129 total
Apr 5 - Apr 6
Total with taxes and fees
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 ...
7.4/10 Good! (2,540 reviews)
Room was nice and tidy

Reviewed on Apr 2, 2026

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
$55 nightly
The price is $62 total per night from Apr 26 to Apr 27
$62 total
Apr 26 - Apr 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! (1,898 reviews)
Good enough for cheap price

Reviewed on Apr 1, 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
$136 nightly
The price is $160 total per night from Apr 12 to Apr 13
$160 total
Apr 12 - Apr 13
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 ...
8.2/10 Very Good! (2,799 reviews)
Breakfast had lots of options. Bathrooms needed major upgrade as they were very outdated and rundown. Beds were very comfortable.

Reviewed on Apr 2, 2026

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
$209 nightly
The price is $241 total per night from Apr 26 to Apr 27
$241 total
Apr 26 - Apr 27
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! (2,351 reviews)
All the staff we encountered were very friendly and most helpful. The pillows were really comfortable. Had to wait a while for the water in the shower to get warm, and the high pressure coming through the small shower head holes hurt your skin when it hit you. Other than that, good stay.

Reviewed on Apr 2, 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
$127 nightly
The price is $149 total per night from Apr 12 to Apr 13
$149 total
Apr 12 - Apr 13
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! (5,806 reviews)
Overall nice hotel great service

Reviewed on Apr 2, 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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