Cheap flights from Valparaiso, Florida to Chicago from $68
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Valparaiso, Florida to Chicago departing on 11/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 10/23
6:07 pm-8:25 pm
Nonstop2h 18m
Chicago Midway
Mon 10/26
6:44 pm-8:55 pm
Nonstop2h 11m
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 10/23
6:07 pm-8:25 pm
Nonstop2h 18m
Chicago Midway
Mon 10/26
6:44 pm-8:55 pm
Nonstop2h 11m
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 10/23
6:07 pm-8:25 pm
Nonstop2h 18m
Chicago Midway
Mon 10/26
6:44 pm-8:55 pm
Nonstop2h 11m
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 10/23
6:07 pm-8:25 pm
Nonstop2h 18m
Chicago Midway
Mon 10/26
6:44 pm-8:55 pm
Nonstop2h 11m
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 10/23
12:00 pm-11:43 pm
2 stops35h 43m
Chicago Midway
Mon 10/26
6:44 pm-8:55 pm
Nonstop2h 11m
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Thu 10/29
3:13 pm-1:36 pm
1 stop22h 23m
Chicago Midway
Sun 11/1
6:42 pm-4:36 pm
2 stops21h 54m
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - ORD Chicago O'Hare Intl
VPSORD
Valparaiso Destin-Ft Walton Beach
Thu 10/29
11:09 am-12:23 pm
1 stop25h 14m
Chicago O'Hare Intl
Sun 11/1
6:30 am-11:37 pm
1 stop17h 07m
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - ORD Chicago O'Hare Intl
VPSORD
Valparaiso Destin-Ft Walton Beach
Tue 12/8
11:32 am-2:21 pm
Nonstop2h 49m
Chicago O'Hare Intl
Fri 12/11
8:27 am-11:02 am
Nonstop2h 35m
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - ORD Chicago O'Hare Intl
VPSORD
Valparaiso Destin-Ft Walton Beach
Sat 11/14
11:39 am-2:19 pm
Nonstop2h 40m
Chicago O'Hare Intl
Sun 11/15
8:34 am-11:09 am
Nonstop2h 35m
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - ORD Chicago O'Hare Intl
VPSORD
Valparaiso Destin-Ft Walton Beach
Tue 12/8
7:09 am-12:19 pm
1 stop5h 10m
Chicago O'Hare Intl
Fri 12/11
8:27 am-11:02 am
Nonstop2h 35m
See travel insights to Chicago from
How to get the cheapest flight ticket from Valparaiso, Florida to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Valparaiso, Florida and Chicago?
Prices are currently typical for flights on this route.
Typical prices usually range from $138 to $543.The lowest price recently found on this route was $157.
What is the cheapest month to fly to Chicago?
The month of August is, on average, the cheapest month to fly to Chicago from Valparaiso, Florida, with most prices found around $139. If you’re not able to fly to Chicago in August, then February is your next best option. Flight prices from Valparaiso, Florida to Chicago during February average around $149.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Sunday when prices can be found for as low as $376. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Valparaiso, Florida to Chicago for around $611.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Valparaiso, Florida to Chicago during this time can be as low as $154. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $526.
What is the cheapest Valparaiso Destin-Ft Walton Beach to Chicago flight route?
Fly from Valparaiso Destin-Ft Walton Beach to Chicago Midway for the best Valparaiso Destin-Ft Walton Beach - Chicago flight prices
What cabin class options are available on Valparaiso, Florida to Chicago flights?
There are 3 cabin classes available to choose from on Valparaiso, Florida to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Valparaiso, Florida to Chicago flights?
No. A direct flight is the cheapest option for a flight between Valparaiso, Florida to Chicago.
What is the cheapest airline that flies from Valparaiso Destin-Ft Walton Beach to Chicago?
Allegiant Air, Sun Country Air, and Southwest are the most popular carriers operating from Valparaiso Destin-Ft Walton Beach to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Valparaiso, Florida according to our data. United Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
When to book flights from Valparaiso, Florida to Chicago
Cheap Valparaiso, Florida to Chicago (VPS to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Valparaiso, Florida to Chicago
Frequently asked questions about flying from Valparaiso, Florida to Chicago
How far is Valparaiso Destin-Ft Walton Beach to Chicago by plane?
Valparaiso Destin-Ft Walton Beach and Chicago are 787.3 mi apart from one another. Flights usually cover this in 2h 18m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago?
Prices for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago are updated daily.
How many operators does momondo search for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago?
As of October 2026, there are 2 operators available to choose from for flights from Valparaiso Destin-Ft Walton Beach Airport to Chicago.
How old do you have to be to fly from Valparaiso Destin-Ft Walton Beach Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Valparaiso Destin-Ft Walton Beach Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Valparaiso, Florida to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Valparaiso, Florida to Chicago is Airbus A319 (30.19% of total bookings). The next most popular plane models are Embraer 175 (16.98%), Boeing 737-800 (11.32%), and Boeing 737-700 (9.43%).
What is the most popular airline from Valparaiso, Florida to Chicago?
momondo data reveals that the most frequently booked airline on the route from Valparaiso, Florida to Chicago is American Airlines, representing 69% of all bookings. The subsequent popular airline is Allegiant Air at 31%.
Best airlines flying from Valparaiso, Florida to Chicago
Compare and see reviews for airlines that fly from Valparaiso, Florida to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $86 | Free Cancellation | Rating 7.3 678 reviews | |||
| PriceFrom $295 | Free Cancellation | Rating 7.0 12,158 reviews |
Allegiant Air Flights From Valparaiso, Florida to Chicago
The lowest priced Allegiant Air flight from Valparaiso, Florida to Chicago from the last 72 hours was $86. Generally, Allegiant Air has 1 flight on this route every week with an average price of $161. Allegiant Air is rated 7.3/10 by our users.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Valparaiso to Chicago?
Finding the right flight to Chicago from Valparaiso is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Valparaiso to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Valparaiso with this policy.
How can momondo help me find flights from Valparaiso to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Valparaiso. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Valparaiso to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Valparaiso. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.