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 $134 One Way, $257 Round Trip

Prices starting at $257 for return flights and $134 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.

Wed, Oct 7 - Sat, Oct 10
RSW
Fort Myers
ORD
Chicago
$257 Roundtrip, found 5 days ago
$257
Roundtrip
found 5 days ago
Select United flight, departing Wed, Oct 7 from Fort Myers to Chicago, returning Sat, Oct 10, priced at $257 found 5 days ago
Wed, Oct 7 - Sat, Oct 10
RSW
Fort Myers
ORD
Chicago
$267 Roundtrip, found 5 days ago
$267
Roundtrip
found 5 days ago
Select United flight, departing Wed, Oct 7 from Fort Myers to Chicago, returning Sat, Oct 10, priced at $267 found 5 days ago
Thu, Nov 5 - Tue, Nov 10
RSW
Fort Myers
ORD
Chicago
$269 Roundtrip, found 4 days ago
$269
Roundtrip
found 4 days ago
Select United flight, departing Thu, Nov 5 from Fort Myers to Chicago, returning Tue, Nov 10, priced at $269 found 4 days ago
Wed, Sep 2 - Thu, Sep 10
RSW
Fort Myers
ORD
Chicago
$276 Roundtrip, found 6 days ago
$276
Roundtrip
found 6 days ago
Select United flight, departing Wed, Sep 2 from Fort Myers to Chicago, returning Thu, Sep 10, priced at $276 found 6 days ago
Tue, Aug 18 - Tue, Aug 25
RSW
Fort Myers
ORD
Chicago
$277 Roundtrip, found 5 days ago
$277
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Aug 18 from Fort Myers to Chicago, returning Tue, Aug 25, priced at $277 found 5 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
$229 nightly
The price is $269 total per night from Aug 7 to Aug 8
$269 total
Aug 7 - Aug 8
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! (2,328 reviews)
"Very convenient to get up & walk to your flight. Good soundproofing."

Reviewed on Jul 7, 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
$169 nightly
The price is $193 total per night from Jul 8 to Jul 9
$193 total
Jul 8 - Jul 9
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! (2,791 reviews)
"Everything"

Reviewed on Jul 6, 2026

Hyatt Regency O'Hare Chicago
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
$129 nightly
The price is $147 total per night from Aug 6 to Aug 7
$147 total
Aug 6 - Aug 7
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! (2,969 reviews)
"Every thing was good and clean"

Reviewed on Jul 6, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr 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

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
$170 nightly
The price is $203 total per night from Jul 8 to Jul 9
$203 total
Jul 8 - Jul 9
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,866 reviews)
"Vas room, AC was broken, lots of dust … Old"

Reviewed on Jul 7, 2026

Omni Chicago 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
$163 nightly
The price is $193 total per night from Jul 27 to Jul 28
$193 total
Jul 27 - Jul 28
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 ...
8.2/10 Very Good! (1,701 reviews)
"HIDDEN FEES WILL CHARGE DOUBLE"

Reviewed on Jul 6, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$181 nightly
The price is $215 total per night from Jul 8 to Jul 9
$215 total
Jul 8 - Jul 9
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! (10,194 reviews)
"Bartender, Chris was very nice!"

Reviewed on Jul 6, 2026

Congress Plaza 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
$65 nightly
The price is $73 total per night from Jul 20 to Jul 21
$73 total
Jul 20 - Jul 21
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! (1,973 reviews)
"Everything was Satisfactory"

Reviewed on Jul 6, 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
$121 nightly
The price is $134 total per night from Jul 9 to Jul 10
$134 total
Jul 9 - Jul 10
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 ...
7.6/10 Good! (1,566 reviews)
"The hotel was clean and met my needs."

Reviewed on Jul 6, 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
$118 nightly
The price is $135 total per night from Jul 12 to Jul 13
$135 total
Jul 12 - Jul 13
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! (3,045 reviews)
"Breakfast was good. Staff was friendly and helpful. Very close to the O’Hare blue line station which takes you downtown."

Reviewed on Jul 6, 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
$152 nightly
The price is $180 total per night from Jul 8 to Jul 9
$180 total
Jul 8 - Jul 9
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. ...
7.8/10 Good! (3,155 reviews)
"The decor was excellent!!!!!! Inviting, relaxing atmosphere the music was great!! Which that was playing in the sitting area. I will definitely stay there again. Close to public transportation, walking distance from shopping, restaurants and the food service there was good."

Reviewed on Jul 6, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$145 nightly
The price is $172 total per night from Jul 8 to Jul 9
$172 total
Jul 8 - Jul 9
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 ...
7.6/10 Good! (2,669 reviews)
"Good"

Reviewed on Jul 7, 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
$65 nightly
The price is $73 total per night from Jul 20 to Jul 21
$73 total
Jul 20 - Jul 21
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! (1,973 reviews)
"Everything was Satisfactory"

Reviewed on Jul 6, 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
$253 nightly
The price is $300 total per night from Jul 19 to Jul 20
$300 total
Jul 19 - Jul 20
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! (2,899 reviews)
"Overall our stay was fine. The rooms were clean. When I texted the staff the answered quickly. Unfortunately 2 of the 4 elevators were "getting repaired" during our 5-day trip, but I never saw anyone working on them. Those things happen, but some sort of compensation would have been nice as it took ..."

Reviewed on Jul 6, 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
$258 nightly
The price is $307 total per night from Aug 6 to Aug 7
$307 total
Aug 6 - Aug 7
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! (2,507 reviews)
"The rooms were clean. And they helped when we need directions but I do beleive that little bit more directions and how to get around Chicago would have been nice"

Reviewed on Jul 6, 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
$198 nightly
The price is $235 total per night from Jul 19 to Jul 20
$235 total
Jul 19 - Jul 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! (6,006 reviews)
"Great hotel in Chicago. The staff are amazing, rooms are clean, and the breakfast and daily snacks/cocktails are a plus. I highly recommend this hotel."

Reviewed on Jul 7, 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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