$82 Cheap flight deals from Chicago (CHI) to Holmes Beach (PIE)

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This Weekend's Flight Deals from Chicago to Holmes Beach

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, Aug 10 - Tue, Aug 12
MDW
Midway Intl.
SRQ
Sarasota-Bradenton Intl.
$416 Roundtrip, found 6 days ago
$416
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Aug 10 from Midway Intl. to Sarasota-Bradenton Intl., returning Tue, Aug 12, priced at $416 found 6 days ago
Sun, Aug 10 - Wed, Aug 13
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$472 Roundtrip, found 6 days ago
$472
Roundtrip
found 6 days ago
Select United flight, departing Sun, Aug 10 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Wed, Aug 13, priced at $472 found 6 days ago

Airfares from $82 One Way, $203 Round Trip from Chicago to Holmes Beach

Prices starting at $203 for return flights and $82 for one-way flights to Holmes Beach were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Aug 26 - Sat, Aug 30
ORD
Chicago
SRQ
Sarasota
$203 Roundtrip, found 6 days ago
$203
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Aug 26 from Chicago to Sarasota, returning Sat, Aug 30, priced at $203 found 6 days ago
Sun, Oct 12 - Thu, Oct 16
MDW
Chicago
SRQ
Sarasota
$223 Roundtrip, found 15 hours ago
$223
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sun, Oct 12 from Chicago to Sarasota, returning Thu, Oct 16, priced at $223 found 15 hours ago
Thu, Oct 16 - Sun, Oct 19
MDW
Chicago
SRQ
Sarasota
$228 Roundtrip, found 3 days ago
$228
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Oct 16 from Chicago to Sarasota, returning Sun, Oct 19, priced at $228 found 3 days ago
Tue, Dec 2 - Fri, Dec 5
ORD
Chicago
SRQ
Sarasota
$241 Roundtrip, found 6 days ago
$241
Roundtrip
found 6 days ago
Select United flight, departing Tue, Dec 2 from Chicago to Sarasota, returning Fri, Dec 5, priced at $241 found 6 days ago
Mon, Oct 6 - Thu, Oct 9
ORD
Chicago
SRQ
Sarasota
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago
Select United flight, departing Mon, Oct 6 from Chicago to Sarasota, returning Thu, Oct 9, priced at $277 found 2 days ago

Holmes Beach economy flight packages

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG
3.5-star property

voco Sarasota by IHG

9.2/10 Wonderful! (1,008 reviews)

Sep 12 - Sep 15

3 night stay

Chicago (CHI) to Tampa (TPA)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Hotel was great. They are close to restaurants and have a shuttle that will take you places like St Armand’s Circle. They also have beach towels, chairs and umbrellas that you can use at the beach. We would stay at hotel again for sure.

Reviewed on Jun 30, 2024

Cedar Cove Resort and Cottages
3.0-star property

Cedar Cove Resort and Cottages

9.2/10 Wonderful! (452 reviews)

Sep 11 - Sep 14

3 night stay

Chicago (CHI) to Sarasota (SRQ)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 23 hours ago
had a great time and very friendly staff

Reviewed on Nov 30, 2024

Ocean Club Treasure Island Hotel
4.0-star property

Ocean Club Treasure Island Hotel

9.6/10 Exceptional! (557 reviews)

Sep 11 - Sep 14

3 night stay

Chicago (CHI) to Tampa (TPA)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 23 hours ago
This was our second time staying at this property. We stayed for eight nights this time. The rooms are lovely but our stay was not nearly as enjoyable as the first time a year ago. There were a lot of children there during our stay. It was practically impossible to use the pool because the kids took over with their inflatables and games. We will likely look elsewhere next time due to the volume of children.

Reviewed on Apr 29, 2025

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Holmes Beach packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Hotel Alba, Tapestry Collection by Hilton
4.0-star property

Hotel Alba, Tapestry Collection by Hilton

8.8/10 Excellent! (2,016 reviews)

Sep 7 - Sep 12

5 night stay

Chicago (MDW) to Sarasota (SRQ)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 11 hours ago
Extremely clean room but Lighting could’ve been better

Reviewed on Aug 3, 2025

Landing Apartments near Sun City Center and Riverview
4.0-star property

Landing Apartments near Sun City Center and Riverview

No reviews

Sep 7 - Sep 12

5 night stay

Chicago (MDW) to Sarasota (SRQ)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 11 hours ago
Hotel Tampa Riverwalk
4.0-star property

Hotel Tampa Riverwalk

7/10 Good! (1,550 reviews)

Sep 7 - Sep 12

5 night stay

Chicago (MDW) to Sarasota (SRQ)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 11 hours ago
We chose this hotel based on proximity to the cruise ship port. The staff was excellent, the room was great but the dinner was not good. My wife chose the hamburger and it was clearly frozen and barely warm. It almost seemed that the wait staff was also handling the cooking. The breakfast was excellent and saved this stay from a lower rating.

Reviewed on Jul 14, 2025

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More About Flying To Holmes Beach from Chicago

Route Information for Flights from Chicago to Holmes Beach

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

Chicago to Holmes Beach

If you are looking to get guaranteed low prices for Chicago to Holmes Beach flights then Orbitz is the place to go. We use cutting edge mobile tools to find the best deals on air tickets and to keep you updated on delays and changes.

Get Package Savings by Booking Flights and Hotels at the Same Time

Using the Orbitz Matrix display, you can see how much you will save on flights from Chicago to Holmes Beach if the discount fare is combined with a hotel. You can also look at hotel reviews, photos and maps of the area, so it will be convenient to make your budget travel plans.

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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.