$34 Cheap flight deals from Chicago (CHI) to Davenport (ORL)

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This Weekend's Flight Deals from Chicago to Davenport

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Nov 9 - Thu, Nov 13
ORD
O'Hare Intl.
MCO
Orlando Intl.
$176 Roundtrip, just found
$176
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Nov 9 from O'Hare Intl. to Orlando Intl., returning Thu, Nov 13, priced at $176 just found
Fri, Nov 7 - Fri, Nov 14
MDW
Midway Intl.
MCO
Orlando Intl.
$181 Roundtrip, just found
$181
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Nov 7 from Midway Intl. to Orlando Intl., returning Fri, Nov 14, priced at $181 just found
Fri, Nov 7 - Wed, Nov 12
RFD
Greater Rockford
MCO
Orlando Intl.
$352 Roundtrip, found 6 days ago
$352
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Nov 7 from Greater Rockford to Orlando Intl., returning Wed, Nov 12, priced at $352 found 6 days ago

Airfares from $34 One Way, $67 Round Trip from Chicago to Davenport

Prices starting at $67 for return flights and $34 for one-way flights to Davenport were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Nov 16 - Sun, Dec 7
ORD
Chicago
MCO
Orlando
$67 Roundtrip, found 4 days ago
$67
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Nov 16 from Chicago to Orlando, returning Sun, Dec 7, priced at $67 found 4 days ago
Mon, Feb 2 - Wed, Feb 4
ORD
Chicago
MCO
Orlando
$84 Roundtrip, just found
$84
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Feb 2 from Chicago to Orlando, returning Wed, Feb 4, priced at $84 just found
Mon, Feb 2 - Thu, Feb 5
ORD
Chicago
MCO
Orlando
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Feb 2 from Chicago to Orlando, returning Thu, Feb 5, priced at $137 just found
Sat, Feb 7 - Sat, Feb 14
ORD
Chicago
MCO
Orlando
$137 Roundtrip, just found
$137
Roundtrip
just found
Select United flight, departing Sat, Feb 7 from Chicago to Orlando, returning Sat, Feb 14, priced at $137 just found
Sat, Feb 7 - Sat, Feb 14
ORD
Chicago
MCO
Orlando
$137 Roundtrip, just found
$137
Roundtrip
just found
Select American Airlines flight, departing Sat, Feb 7 from Chicago to Orlando, returning Sat, Feb 14, priced at $137 just found

Davenport economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

8.8/10 Excellent! (1,037 reviews)

Dec 26 - Dec 31

5 night stay

Chicago (CHI) to Orlando (MCO)

Southwest Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Coach
Price was $1,442, price is now $672 per person
$672
per person
found 1 day ago
The location is conveniently close to Universal, with a nearby 7-Eleven and several restaurants. The room is clean and pleasant, and parking is easily accessible.

Reviewed on Aug 6, 2025

Summerville Vacation Homes by Columbia Management
4.0-star property

Summerville Vacation Homes by Columbia Management

8.4/10 Very Good! (152 reviews)

Dec 26 - Dec 31

5 night stay

Chicago (CHI) to Orlando (MCO)

Southwest Airlines • Coach

Orlando (MCO) to Chicago (CHI)

Spirit Airlines • Coach
Price was $2,364, price is now $1,078 per person
$1,078
per person
found 1 day ago
This concept is nicer than staying in a hotel room. The home was spacious and decorated very well. All necessities were provided. However, the ice maker in the refrigerator was not working. We were only there for 3 nights so I didn’t bother management with it.

Reviewed on Apr 19, 2021

Westgate Cocoa Beach Resort
4.0-star property

Westgate Cocoa Beach Resort

8.8/10 Excellent! (494 reviews)

Dec 23 - Dec 30

7 night stay

Chicago (MDW) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $2,809, price is now $1,398 per person
$1,398
per person
found 9 hours ago
Sue behind the bar was amazing. Hotel is a little dated and could use a new external color scheme. Rooms were modernized and mostly clean (sofa needs vacuumed) We had a great time and made use of all the pool areas and took advantage of happy hour every day. It is a bit of a walk from the main part of the resort to the beach so keep that in mind. Great place for family relaxing

Reviewed on Oct 5, 2025

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More About Flying To Davenport from Chicago

Route Information for Flights from Chicago to Davenport

Origin Airport IATA Code
CHI
Destination Airport IATA Code
ORL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Davenport

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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.