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, $74 Round Trip

Prices starting at $74 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.

Sat, May 2 - Sun, May 10
RSW
Fort Myers
ORD
Chicago
$74 Roundtrip, found 6 days ago
$74
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 2 from Fort Myers to Chicago, returning Sun, May 10, priced at $74 found 6 days ago
Thu, May 14 - Sun, May 17
RSW
Fort Myers
ORD
Chicago
$105 Roundtrip, found 4 days ago
$105
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, May 14 from Fort Myers to Chicago, returning Sun, May 17, priced at $105 found 4 days ago
Mon, May 11 - Thu, May 14
RSW
Fort Myers
ORD
Chicago
$111 Roundtrip, found 4 days ago
$111
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Mon, May 11 from Fort Myers to Chicago, returning Thu, May 14, priced at $111 found 4 days ago
Wed, Apr 22 - Sat, Apr 25
RSW
Fort Myers
ORD
Chicago
$182 Roundtrip, found 6 days ago
$182
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Apr 22 from Fort Myers to Chicago, returning Sat, Apr 25, priced at $182 found 6 days ago
Wed, Apr 22 - Sat, Apr 25
RSW
Fort Myers
ORD
Chicago
$183 Roundtrip, found 6 days ago
$183
Roundtrip
found 6 days ago
Select United flight, departing Wed, Apr 22 from Fort Myers to Chicago, returning Sat, Apr 25, priced at $183 found 6 days ago

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
$196 nightly
The price is $230 total per night from Apr 3 to Apr 4
$230 total
Apr 3 - Apr 4
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! (2,217 reviews)
We only stayed because we had to make a connection in the morning and it is the hotel attached to the airport

Reviewed on Mar 10, 2026

Hilton Chicago O'Hare Airport
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
$118 nightly
The price is $135 total per night from Mar 22 to Mar 23
$135 total
Mar 22 - Mar 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 breakfast ...
9/10 Wonderful! (2,888 reviews)
Excellent

Reviewed on Mar 12, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG
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 6 to Apr 7
$154 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 helpful staff ...
8.8/10 Excellent! (2,395 reviews)
Stayed for one night and it was great

Reviewed on Mar 12, 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
$101 nightly
The price is $118 total per night from Apr 1 to Apr 2
$118 total
Apr 1 - Apr 2
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! (9,918 reviews)
The hotel is very dated. Room had stale smell. Staff brought us extra sheets and fans to keep the room cooler. The staff what there is was helpful. No one really is around.

Reviewed on Mar 13, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$156 nightly
The price is $183 total per night from Mar 30 to Mar 31
$183 total
Mar 30 - Mar 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (3,521 reviews)
Good breakfast, excellent service, unfortunately, they don't have microwave service to heat food

Reviewed on Mar 13, 2026

Hotel Riu Plaza Chicago
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
$122 nightly
The price is $143 total per night from Mar 19 to Mar 20
$143 total
Mar 19 - Mar 20
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! (5,735 reviews)
Great location. Good amenities. Nice breakfast. Comfy beds. Quiet.

Reviewed on Mar 12, 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
$50 nightly
The price is $56 total per night from Apr 2 to Apr 3
$56 total
Apr 2 - Apr 3
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! (1,864 reviews)
Everything was fine but I didn't get room service for 4 days.

Reviewed on Mar 11, 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
$91 nightly
The price is $101 total per night from Mar 22 to Mar 23
$101 total
Mar 22 - Mar 23
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! (1,297 reviews)
Staff was super friendly, rooms were big and clean and the breakfast was great!

Reviewed on Mar 12, 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
$84 nightly
The price is $97 total per night from Apr 1 to Apr 2
$97 total
Apr 1 - Apr 2
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! (2,932 reviews)
Yes easy to find. None of the 3 different ice makers worked

Reviewed on Mar 12, 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
$80 nightly
The price is $94 total per night from Mar 25 to Mar 26
$94 total
Mar 25 - Mar 26
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! (2,803 reviews)
Loved my stay. The cushions for the couch in the bedroom could’ve used a good wash. It’s exacting in the walking distance of everything which I was surprised about. I will be staying again.

Reviewed on Mar 10, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$103 nightly
The price is $121 total per night from Mar 18 to Mar 19
$121 total
Mar 18 - Mar 19
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! (2,527 reviews)
Water wasnt very hot

Reviewed on Mar 12, 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
$50 nightly
The price is $56 total per night from Apr 2 to Apr 3
$56 total
Apr 2 - Apr 3
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! (1,864 reviews)
Everything was fine but I didn't get room service for 4 days.

Reviewed on Mar 11, 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
$139 nightly
The price is $163 total per night from Mar 22 to Mar 23
$163 total
Mar 22 - Mar 23
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! (2,795 reviews)
Good

Reviewed on Mar 10, 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
$159 nightly
The price is $183 total per night from Apr 5 to Apr 6
$183 total
Apr 5 - Apr 6
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! (2,331 reviews)
Clean rooms, great staff, great amenities. Next to the loop and the red line. In the heart of downtown Chicago, very historic and beautiful.

Reviewed on Mar 12, 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
$122 nightly
The price is $143 total per night from Mar 19 to Mar 20
$143 total
Mar 19 - Mar 20
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! (5,735 reviews)
Great location. Good amenities. Nice breakfast. Comfy beds. Quiet.

Reviewed on Mar 12, 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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