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Cheap Flights from Chicago to Orlando

Explore the cheapest flights from Chicago to Orlando in the next three months. Based on Trip.com's data from the latest 7 days, one-way direct flights start at S$ 37, and round-trip direct tickets start at S$ 93.

      • Cheapest nonstop
        ORD 16:59
        3h 2m
        Direct
        MCO 21:01
        Chicago - Orlando | Wed, Jul 1 | Frontier Airlines
        MCO 07:00
        3h 21m
        Direct
        ORD 09:21
        Orlando - Chicago | Fri, Jul 3 | Frontier Airlines
        S$ 93 S$ 274
        66% off
        66% off
        S$ 274 S$ 93
      • ORD 17:11
        3h 2m
        Direct
        MCO 21:13
        Chicago - Orlando | Tue, Jun 2 | Frontier Airlines
        MCO 05:30
        5h 43m
        1 stop
        ORD 10:13
        Orlando - Chicago | Tue, Jun 9 | Delta Air Lines
        S$ 157 S$ 274
        43% off
        43% off
        S$ 274 S$ 157
      • ORD 17:11
        3h 2m
        Direct
        MCO 21:13
        Chicago - Orlando | Wed, Jun 3 | Frontier Airlines
        MCO 05:30
        5h 39m
        1 stop
        MDW 10:09
        Orlando - Chicago | Tue, Jun 9 | Delta Air Lines
        S$ 158 S$ 274
        42% off
        42% off
        S$ 274 S$ 158
      • ORD 17:11
        3h 2m
        Direct
        MCO 21:13
        Chicago - Orlando | Tue, May 26 | Frontier Airlines
        MCO 12:48
        8h 44m
        1 stop
        ORD 20:32
        Orlando - Chicago | Mon, Jun 1 | Frontier Airlines
        S$ 173
        37% off
        S$ 274 S$ 173
      • ORD 11:30
        7h 19m
        1 stop
        MCO 19:49
        Chicago - Orlando | Tue, Jun 30 | Delta Air Lines
        MCO 21:01
        3h 18m
        Direct
        ORD 23:19
        Orlando - Chicago | Sat, Jul 4 | Frontier Airlines
        S$ 178
        35% off
        S$ 274 S$ 178
      • ORD 17:11
        3h 2m
        Direct
        MCO 21:13
        Chicago - Orlando | Thu, May 28 | Frontier Airlines
        MCO 17:10
        5h 52m
        1 stop
        MDW 22:02
        Orlando - Chicago | Wed, Jun 3 | Frontier Airlines
        S$ 181
        34% off
        S$ 274 S$ 181
      • MDW 12:27
        8h 42m
        1 stop
        MCO 22:09
        Chicago - Orlando | Tue, Jun 30 | Frontier Airlines
        MCO 21:01
        3h 18m
        Direct
        ORD 23:19
        Orlando - Chicago | Sat, Jul 4 | Frontier Airlines
        S$ 184
        33% off
        S$ 274 S$ 184
      • ORD 16:59
        3h 2m
        Direct
        MCO 21:01
        Chicago - Orlando | Fri, Jul 3 | Frontier Airlines
        MCO 13:45
        7h 8m
        1 stop
        ORD 19:53
        Orlando - Chicago | Wed, Jul 8 | Frontier Airlines
        S$ 192
        30% off
        S$ 274 S$ 192
      • ORD 16:59
        3h 2m
        Direct
        MCO 21:01
        Chicago - Orlando | Tue, Jun 16 | Frontier Airlines
        MCO 15:10
        5h 40m
        1 stop
        ORD 19:50
        Orlando - Chicago | Mon, Jun 22 | Frontier Airlines
        S$ 193
        30% off
        S$ 274 S$ 193
      • ORD 16:59
        3h 2m
        Direct
        MCO 21:01
        Chicago - Orlando | Wed, Jun 24 | Frontier Airlines
        MCO 06:15
        4h 58m
        1 stop
        ORD 10:13
        Orlando - Chicago | Wed, Jul 1 | Delta Air Lines
        S$ 197
        28% off
        S$ 274 S$ 197
      • CHI 13:00
        17h 25m
        1 stop
        ORL 14:00
        Chicago - Orlando | Sat, May 16 | Normal Airline
        ORL 15:00
        6h
        Direct
        CHI 16:00
        Orlando - Chicago | Mon, May 18 | Normal Airline
        Find more flights
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      • Cheapest nonstop
        ORD 17:11
        3h 2m
        Direct
        MCO 21:13
        Chicago - Orlando | Thu, Jun 4 | Frontier Airlines
        S$ 37 S$ 152
        76% off
        76% off
        S$ 152 S$ 37
      • ORD 16:59
        3h 2m
        Direct
        MCO 21:01
        Chicago - Orlando | Sat, Jul 4 | Frontier Airlines
        S$ 65 S$ 152
        56% off
        56% off
        S$ 152 S$ 65
      • ORD 17:11
        3h 2m
        Direct
        MCO 21:13
        Chicago - Orlando | Fri, Jun 5 | Frontier Airlines
        S$ 79 S$ 152
        48% off
        48% off
        S$ 152 S$ 79
      • ORD 07:29
        2h 49m
        Direct
        MCO 11:18
        Chicago - Orlando | Wed, Jun 24 | United Airlines
        S$ 108
        28% off
        S$ 152 S$ 108
      • ORD 07:29
        2h 49m
        Direct
        MCO 11:18
        Chicago - Orlando | Thu, Jun 4 | United Airlines
        S$ 108
        28% off
        S$ 152 S$ 108
      • ORD 07:29
        2h 49m
        Direct
        MCO 11:18
        Chicago - Orlando | Wed, Jun 3 | United Airlines
        S$ 108
        28% off
        S$ 152 S$ 108
      • ORD 11:09
        7h 30m
        1 stop
        MCO 19:39
        Chicago - Orlando | Sun, May 31 | Delta Air Lines
        S$ 105
        31% off
        S$ 152 S$ 105
      • MDW 17:11
        4h 40m
        1 stop
        MCO 22:51
        Chicago - Orlando | Wed, Jun 17 | Delta Air Lines
        S$ 108
        28% off
        S$ 152 S$ 108
      • CHI 13:00
        17h 25m
        1 stop
        ORL 14:00
        Chicago - Orlando | Sat, May 16 | Normal Airline
        Find more flights
        Find more flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Trip.com Price Insights on Flights from Chicago to Orlando.

What is the cheapest month for one-way flights from to Orlando?

The average price of one-way flights from to Orlando purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for flights from to Orlando is January, with an average price of S$ 138, and the most expensive month is December, with an average price of up to S$ 237.

S$ 237
S$ 188
S$ 138
S$ 89
    Cheapest
  • S$ 142
    May
  • S$ 176
    Jun
  • S$ 172
    Jul
  • S$ 181
    Aug
  • S$ 171
    Sep
  • S$ 166
    Oct
  • S$ 214
    Nov
  • S$ 237
    Dec
  • S$ 138
    Jan
  • S$ 146
    Feb
  • S$ 199
    Mar
  • S$ 195
    Apr

What is the cheapest day to fly from Chicago to Orlando during Hari Raya Haji?

Based on Trip.com's data over the past 3 days, these are the lowest one-way airfares from Chicago to Orlando during Hari Raya Haji.

Hari Raya Haji is scheduled on May 27. The flights from Chicago to Orlando are cheapest on May 28, with the lowest fare of S$ 59.

S$ 164
S$ 112
S$ 59
S$ 7
    Cheapest
  • S$ 122
    23
    May
  • S$ 144
    24
  • S$ 164
    25
  • S$ 113
    26
  • S$ 139
    27
  • S$ 59
    28
  • S$ 150
    29

Frequently Asked Questions

  • Which airlines offer the cheapest flights from Chicago (CHI) to Orlando (ORL)?

    Based on Trip.com data, Frontier Airlines offers one-way fares as low as S$ 37 on Cheapest nonstop routes (e.g. ORD to MCO on Thu, Jun 4), while Frontier Airlines offers Cheapest nonstop round-trips from S$ 93 departing on Wed, Jul 1 and returning on Fri, Jul 3.
  • It takes about 2 hours 47 minutes to fly from Chicago (CHI) to Orlando (ORL).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Orlando is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • To find best deals on flights from Chicago to Orlando, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Thu, Jun 4, with one-way flights priced at just S$ 37.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Frontier Airlines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Orlando travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Chicago to Orlando is October, when demand for travel is lower.
  • After crunching the numbers on our May flight calendar, it's currently cheapest to fly from Chicago to Orlando on May 27, 2026 with Frontier Airlines, with prices starting at S$ 37.
  • The time difference between Orlando and Chicago is 1h.
  • Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

Find Cheap Flights & Deals on Trip.com

Note: Prices shown on this page are the lowest estimated prices found in the last 24 hours and include all taxes and fees.

Book with no extra fees

Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are shown before payment. Charges for checked baggage, meals, Wi-Fi, and other optional services may also appear in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and with many routes refreshed in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.