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 $45 One Way, $90 Round Trip

Prices starting at $90 for return flights and $45 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 23 - Thu, Apr 30
RSW
Fort Myers
ORD
Chicago
$90 Roundtrip, found 16 hours ago
$90
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Thu, Apr 23 from Fort Myers to Chicago, returning Thu, Apr 30, priced at $90 found 16 hours ago
Sat, Apr 25 - Thu, Apr 30
RSW
Fort Myers
ORD
Chicago
$101 Roundtrip, found 3 days ago
$101
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Apr 25 from Fort Myers to Chicago, returning Thu, Apr 30, priced at $101 found 3 days ago
Fri, Apr 24 - Sun, Apr 26
RSW
Fort Myers
ORD
Chicago
$167 Roundtrip, found 3 hours ago
$167
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Fri, Apr 24 from Fort Myers to Chicago, returning Sun, Apr 26, priced at $167 found 3 hours ago
Thu, May 28 - Mon, Jun 1
RSW
Fort Myers
ORD
Chicago
$295 Roundtrip, found 4 days ago
$295
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, May 28 from Fort Myers to Chicago, returning Mon, Jun 1, priced at $295 found 4 days ago
Mon, Jul 20 - Mon, Aug 3
RSW
Fort Myers
ORD
Chicago
$295 Roundtrip, just found
$295
Roundtrip
just found
Select American Airlines flight, departing Mon, Jul 20 from Fort Myers to Chicago, returning Mon, Aug 3, 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
$204 nightly
The price is $240 total per night from May 9 to May 10
$240 total
May 9 - May 10
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! (2,261 reviews)
I would rate this hotel as good to excellent if not for one employee. I stayed two nights and all the staff including front desk, restaurant and housekeeping were customer friendly and efficient with one exception. I returned back to the main entrance of the hotel on the second night after a long ...

Reviewed on Apr 12, 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
$144 nightly
The price is $164 total per night from Apr 22 to Apr 23
$164 total
Apr 22 - Apr 23
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! (2,491 reviews)
Bathroom in room with a king size bed was the size of a cruise ship bathroom!!!! For the price I found that unacceptable

Reviewed on Apr 17, 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
$122 nightly
The price is $139 total per night from Apr 21 to Apr 22
$139 total
Apr 21 - Apr 22
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! (2,917 reviews)
Customer service was awesome. Of going to Chicago I recommend taking the hotel shuttle back to the airport and grabbing the train from there.

Reviewed on Apr 17, 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
$116 nightly
The price is $137 total per night from Apr 26 to Apr 27
$137 total
Apr 26 - Apr 27
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! (10,128 reviews)
Didn't use bar or car park.

Reviewed on Apr 17, 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 26 to Apr 27
$140 total
Apr 26 - Apr 27
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! (4,137 reviews)
Great location. Clean room. Friendly staff. Pool was kinda chilly. But that’s the only little criticism

Reviewed on Apr 16, 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
$139 nightly
The price is $163 total per night from Apr 26 to Apr 27
$163 total
Apr 26 - Apr 27
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! (5,852 reviews)
The rooms are spacious. While the pool is rather small my kids loved it, and we went every evening. The breakfast was good, and offered a large variety of choices. With the nearby access to the redline I would recommend this hotel for anyone visiting downtown Chicago.

Reviewed on Apr 17, 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 23 to Apr 24
$62 total
Apr 23 - Apr 24
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! (1,926 reviews)
Close to the airport and pet friendly. Walls were very thin. But endless hot water. Generally clean space.

Reviewed on Apr 16, 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
$96 nightly
The price is $107 total per night from Apr 23 to Apr 24
$107 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! (1,363 reviews)
Rooms were filthy. Bedding had stains on it and this is definitely not what the pictures look like online. I brought my son here for his Golden Birthday and was supposed to be nice. Will definitely not be going back.

Reviewed on Apr 16, 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
$78 nightly
The price is $90 total per night from Apr 23 to Apr 24
$90 total
Apr 23 - Apr 24
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! (2,953 reviews)
Amazing service

Reviewed on Apr 16, 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
$91 nightly
The price is $106 total per night from Apr 28 to Apr 29
$106 total
Apr 28 - Apr 29
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. ...
8/10 Very Good! (2,877 reviews)
Staff was very helpful and in a good area in the center of everything.

Reviewed on Apr 17, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$118 nightly
The price is $139 total per night from Apr 26 to Apr 27
$139 total
Apr 26 - Apr 27
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! (2,566 reviews)
Staff was amazing and sweet. Breakfast was awesome

Reviewed on Apr 17, 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 23 to Apr 24
$62 total
Apr 23 - Apr 24
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! (1,926 reviews)
Close to the airport and pet friendly. Walls were very thin. But endless hot water. Generally clean space.

Reviewed on Apr 16, 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
$148 nightly
The price is $174 total per night from Apr 26 to Apr 27
$174 total
Apr 26 - Apr 27
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! (2,813 reviews)
The beds were t

Reviewed on Apr 17, 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
$184 nightly
The price is $214 total per night from May 8 to May 9
$214 total
May 8 - May 9
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! (2,390 reviews)
The hotel is beautiful. The room was clean and furnishings newer. There are a lot of rooms so you could be placed far away from the elevator. For us that was not an issue but I could see it being so for others.

Reviewed on Apr 14, 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
$139 nightly
The price is $163 total per night from Apr 26 to Apr 27
$163 total
Apr 26 - Apr 27
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! (5,852 reviews)
The rooms are spacious. While the pool is rather small my kids loved it, and we went every evening. The breakfast was good, and offered a large variety of choices. With the nearby access to the redline I would recommend this hotel for anyone visiting downtown Chicago.

Reviewed on Apr 17, 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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