$288 Cheap flight deals from Chicago (CHI) to Tupelo (TUP)
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Airfares from $288 One Way, $525 Round Trip from Chicago to Tupelo
Prices starting at $525 for return flights and $288 for one-way flights to Tupelo were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tupelo economy flight packages
Hotel DeSoto
Oct 30 - Nov 1
Chicago (CHI) to Tupelo (TUP)
Tupelo (TUP) to Chicago (CHI)
Reviewed on Jun 8, 2025
Holiday Inn Express & Suites Olive Branch by IHG
Oct 24 - Oct 27
Chicago (MDW) to Tupelo (TUP)
Reviewed on Nov 20, 2023
La Quinta Inn & Suites by Wyndham Olive Branch
Nov 7 - Nov 11
Chicago (CHI) to Tupelo (TUP)
Tupelo (TUP) to Chicago (CHI)
Reviewed on Jun 12, 2025
More About Flying To Tupelo from Chicago
Route Information for Flights from Chicago to Tupelo
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | TUP |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Tupelo
If you are looking to find the best deals on Chicago to Tupelo flights, look no further than Orbitz. Orbitz offers guaranteed low prices as well as cutting-edge mobile tools to help you book cheap flights from Chicago to Tupelo.
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Stay Informed While You Travel
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Keep More Money in Your Pocket With Discount Flights
Orbitz looks for the best deals on Chicago to Tupelo flights for you. Mix and match airlines for your departing and return flights to fit your travel schedule and budget.
Frequently asked questions
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Tupelo Airports
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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.