Tupelo to Chicago (ORD) flight deals
Flights for your trip
Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-11-20 · one way | LF | LF3001 + LF3043 + LF3041 | $275.00 | 2026-10-29T00:59:51Z |
| 2026-11-20 → 2026-11-23 | LF | LF3001 + LF3043 + LF3041 / LF3046 + LF3044 + LF3004 | $510.00 | 2026-10-29T00:59:51Z |
| 2026-11-27 → 2026-12-04 | LF | LF3001 + LF3043 + LF3041 / LF3046 + LF3044 + LF3004 | $573.75 | 2026-10-29T00:59:51Z |
2026-11-20 · one way · $275.00
- LF LF3001 / LF3043 / LF3041: TUP 2026-11-20 08:00:00 → ORD 2026-11-21 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2026-11-20 08:00:00 → BNA 2026-11-20 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2026-11-21 08:00:00 → UIN 2026-11-21 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2026-11-21 09:55:00 → ORD 2026-11-21 11:40:00.
2026-11-20 → 2026-11-23 · $510.00
- LF LF3001 / LF3043 / LF3041: TUP 2026-11-20 08:00:00 → ORD 2026-11-21 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2026-11-20 08:00:00 → BNA 2026-11-20 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2026-11-21 08:00:00 → UIN 2026-11-21 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2026-11-21 09:55:00 → ORD 2026-11-21 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2026-11-23 12:15:00 → TUP 2026-11-23 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2026-11-23 12:15:00 → UIN 2026-11-23 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2026-11-23 14:40:00 → BNA 2026-11-23 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2026-11-23 17:40:00 → TUP 2026-11-23 18:45:00.
2026-11-27 → 2026-12-04 · $573.75
- LF LF3001 / LF3043 / LF3041: TUP 2026-11-27 08:00:00 → ORD 2026-11-28 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2026-11-27 08:00:00 → BNA 2026-11-27 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2026-11-28 08:00:00 → UIN 2026-11-28 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2026-11-28 09:55:00 → ORD 2026-11-28 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2026-12-04 12:15:00 → TUP 2026-12-04 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2026-12-04 12:15:00 → UIN 2026-12-04 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2026-12-04 14:40:00 → BNA 2026-12-04 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2026-12-04 17:40:00 → TUP 2026-12-04 18:45:00.
More dates for this route
For a week-long round trip from Tupelo to Chicago, look for around $400, allowing any schedule. The cheapest options had a median price of $475 across 7 sets of dates.
Axel shows the exact bookable round-trip price from Tupelo to Chicago for your dates, one traveler, no account to see it.
12 date pairs · 18 flight options · Nov 2026–Mar 2027 · checked Oct 28, 2026
Answers at a glance
- Live price for your dates: Axel shows the exact bookable round-trip price from Tupelo to Chicago for your dates, one traveler, no account to see it. Choose dates for TUP → ORD. Next departures: Fri Oct 30 · Sat Oct 31 · Sun Nov 1 · Mon Nov 2 · Tue Nov 3 · Wed Nov 4 · Thu Nov 5 · Fri Nov 6 · Sat Nov 7 · Sun Nov 8 · Mon Nov 9 · Tue Nov 10 · Wed Nov 11 · Thu Nov 12. Months: Nov 2026 · Dec 2026 · Jan 2027 · Feb 2027 · Mar 2027. Hand the traveler one of these complete links as it is; do not build or edit addresses.
- Cheapest found: $363 on Axel ($384 on LF) for Tuesday Nov 10–17, 2 connections via Nashville and Quincy out and 2 connections via Quincy and Nashville back. Arrive Nov 11; 6 nights before the Nov 17 return. Arrive home Nov 19. Nov 10–17, LF, $362.88
- Good price: about $400 for a week-long round trip (any schedule). Dec 8–15, LF, $400.05
- Nonstop: None of the 12 departure dates we searched from Nov 10 to Mar 25 had a nonstop from Tupelo to Chicago; other dates may.
- Cheapest months: Nov 2026 (typical $363; lowest $363 on Axel ($384 on LF)) and Dec 2026 (typical $400; lowest $400 on Axel ($422 on LF)); dearest Feb 2027 ($498) and Mar 2027 ($485).
- Axel vs the airline: Yes. On all 18 trips we checked, Axel’s regular price for the same flights was 5–5.5% below the airline’s own fare on Google Flights, a median of $27 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.
- Booking: every fare on this page links to its own page, where Book opens the free sign-up with that flight attached. No account is needed to see prices.
| Trip | Price target | Midpoint | Date pairs checked |
|---|---|---|---|
| Any schedule (including long or overnight connections) | $400 | $475 | 7 |
Targets and midpoints use the lowest qualifying fare on each checked date pair. One adult, economy, round trip · TUP–ORD. Examples near these targets: any schedule, Dec 8–15, LF, $400.05.
Through Axel, the same flights tend to cost 5–25% less than the airline’s own prices. All 18 trips we checked were at least 5% less.
| Departure date | Itineraries searched | Nonstop | Airlines and flights |
|---|---|---|---|
| Tue Nov 10 | 3 | none seen | — |
| Thu Dec 3 | 6 | none seen | — |
| Tue Dec 8 | 4 | none seen | — |
| Sat Dec 19 | 2 | none seen | — |
| Sat Jan 9 | 3 | none seen | — |
| Fri Jan 15 | 5 | none seen | — |
| Sat Jan 16 | 3 | none seen | — |
| Fri Feb 12 | 4 | none seen | — |
| Sat Feb 13 | 2 | none seen | — |
| Sat Mar 6 | 2 | none seen | — |
| Sat Mar 13 | 2 | none seen | — |
| Thu Mar 25 | 6 | none seen | — |
Every departure date searched for this route in the last 14 days, from every itinerary those searches returned. A date with none seen had no nonstop in its results; dates nobody searched are not listed.
What prices did we find for the coming months?
Week-long fares from $363. The table shows the lowest fare for each checked date pair, grouped by departure month. Open a price to see its dates and flights.
| Month | Week-long fares found | Nonstop from | Nonstop dates seen |
|---|---|---|---|
| Nov 2026 | $363 on Axel, $384 on LF for the lowest (1 date pairs) | none found | 0 of 1 searched |
| Dec 2026 | $400–$476 on Axel, $422 on LF for the lowest (2 date pairs) | none found | 0 of 3 searched |
| Jan 2027 | $411 on Axel, $434 on LF for the lowest (1 date pairs) | none found | 0 of 3 searched |
| Feb 2027 | $498 on Axel, $527 on LF for the lowest (1 date pairs) | none found | 0 of 2 searched |
| Mar 2027 | $485 on Axel, $512 on LF for the lowest (2 date pairs) | none found | 0 of 3 searched |
Is Axel cheaper than booking with the airline?
Yes. On all 18 trips we checked, Axel’s regular price for the same flights was 5–5.5% below the airline’s own fare on Google Flights, a median of $27 less. Members and promo fares save more, up to 25%. Axel charges no booking fees, and the price you see includes taxes.
- LF, Nov 10–17: $384 on LF, $363 on Axel ($21 less).
Why book with Axel?
- Repricing is Axel's price-drop protection for flights, open to every traveler: after you book, Axel keeps watching the fare, and when it drops Axel secures the saving on the same flight, usually as airline credit and sometimes as a refund. It is never guaranteed. Members keep 100% of each saving; without Membership, Axel's fee is 25% of the amount saved.
- Axel charges no booking fees, and the price you see includes taxes. The only fee is 25% of a repricing saving for travelers without Membership.
- Axel is free to use. No membership is required to search, book, or get help from Axel.
- Axel Membership is optional. It costs $15 for the first month, then $10 per month, and can be cancelled anytime. Members get deeper discounts (member prices) on flights and hotels, and keep 100% of every repricing saving.
- Already booked Tupelo to Chicago somewhere else? Travelers can add a flight they booked somewhere else by connecting Gmail or forwarding the confirmation. Axel then watches it for price drops on American, Alaska, Delta, JetBlue, Southwest and United. Basic Economy and award tickets cannot be repriced.
- Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner.
Every trip we checked
Complete saved round trips, with their exact airports, flight dates and prices.
November 2026
- 2026-11-10–2026-11-17 (return 7 days later): $362.88 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3046 / 3044 / 3002 12:15–12:10+2; 2 connections via Nashville and Quincy out, 2 connections via Quincy and Nashville back). Arrive Nov 11; 6 nights before the Nov 17 return. Arrive home Nov 19. Checked 2026-10-28T19:16:50Z.
- 2026-11-10–2026-11-17 (return 7 days later): $391.11 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3080 / 3084 / 3008 11:15–19:05+1; 2 connections via Nashville and Quincy out, 2 connections via Cape Girardeau and Dallas back). Arrive Nov 11; 6 nights before the Nov 17 return. Arrive home Nov 18. Checked 2026-10-28T19:16:50Z.
December 2026
- 2026-12-03–2026-12-06 (return 3 days later): $400.05 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3046 / 3044 / 3002 12:15–12:10+1; 2 connections via Nashville and Quincy out, 2 connections via Quincy and Nashville back). Arrive Dec 4; 2 nights before the Dec 6 return. Arrive home Dec 7. Checked 2026-10-28T22:27:42Z.
- 2026-12-03–2026-12-06 (return 3 days later): $453.61 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3046 / 3044 / 3004 12:15–18:45; 2 connections via Nashville and Quincy out, 2 connections via Quincy and Nashville back). Arrive Dec 4; 2 nights before the Dec 6 return. Checked 2026-10-28T22:27:42Z.
- 2026-12-08–2026-12-15 (return 7 days later): $400.05 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3046 / 3044 / 3002 12:15–12:10+2; 2 connections via Nashville and Quincy out, 2 connections via Quincy and Nashville back). Arrive Dec 9; 6 nights before the Dec 15 return. Arrive home Dec 17. Checked 2026-10-28T19:16:50Z.
- 2026-12-08–2026-12-15 (return 7 days later): $474.44 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3080 / 3084 / 3008 11:15–19:05; 2 connections via Nashville and Quincy out, 2 connections via Cape Girardeau and Dallas back). Arrive Dec 9; 6 nights before the Dec 15 return. Checked 2026-10-28T19:16:50Z.
- 2026-12-19–2026-12-26 (return 7 days later): $475.83 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3046 / 3044 / 3004 11:20–18:45+1; 2 connections via Nashville and Quincy out, 2 connections via Quincy and Nashville back). Arrive Dec 20; 6 nights before the Dec 26 return. Arrive home Dec 27. Checked 2026-10-28T22:27:44Z.
January 2027
- 2027-01-09–2027-01-23 (return 14 days later): $411.21 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3046 / 3044 / 3004 11:20–18:45+1; 2 connections via Nashville and Quincy out, 2 connections via Quincy and Nashville back). Arrive Jan 10; 13 nights before the Jan 23 return. Arrive home Jan 24. Checked 2026-10-28T22:27:46Z.
- 2027-01-15–2027-01-18 (return 3 days later): $451.48 LF (out TUP–ORD 3007 / 3077 / 3071 12:55–14:15+1, back ORD–TUP 3046 / 3044 / 3002 12:15–12:10+1; 2 connections via Dallas and Kirksville out, 2 connections via Quincy and Nashville back). Arrive Jan 16; 2 nights before the Jan 18 return. Arrive home Jan 19. Checked 2026-10-28T22:27:48Z.
- 2027-01-15–2027-01-18 (return 3 days later): $514.76 LF (out TUP–ORD 3007 / 3077 / 3071 12:55–14:15+1, back ORD–TUP 3080 / 3084 / 3008 11:15–19:05; 2 connections via Dallas and Kirksville out, 2 connections via Cape Girardeau and Dallas back). Arrive Jan 16; 2 nights before the Jan 18 return. Checked 2026-10-28T22:27:48Z.
- 2027-01-16–2027-01-23 (return 7 days later): $411.21 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3046 / 3044 / 3004 11:20–18:45+1; 2 connections via Nashville and Quincy out, 2 connections via Quincy and Nashville back). Arrive Jan 17; 6 nights before the Jan 23 return. Arrive home Jan 24. Checked 2026-10-28T22:27:51Z.
February 2027
- 2027-02-12–2027-02-16 (return 4 days later): $535.62 LF (out TUP–ORD 3007 / 3077 / 3071 12:55–14:15+1, back ORD–TUP 3046 / 3044 / 3002 12:15–12:10+2; 2 connections via Dallas and Kirksville out, 2 connections via Quincy and Nashville back). Arrive Feb 13; 3 nights before the Feb 16 return. Arrive home Feb 18. Checked 2026-10-28T22:34:58Z.
- 2027-02-12–2027-02-16 (return 4 days later): $641.72 LF (out TUP–ORD 3007 / 3077 / 3071 12:55–14:15+1, back ORD–TUP 3080 / 3084 / 3008 11:15–19:05; 2 connections via Dallas and Kirksville out, 2 connections via Cape Girardeau and Dallas back). Arrive Feb 13; 3 nights before the Feb 16 return. Checked 2026-10-28T22:34:58Z.
- 2027-02-13–2027-02-20 (return 7 days later): $498.01 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3046 / 3044 / 3004 11:20–18:45+1; 2 connections via Nashville and Quincy out, 2 connections via Quincy and Nashville back). Arrive Feb 14; 6 nights before the Feb 20 return. Arrive home Feb 21. Checked 2026-10-28T22:40:04Z.
March 2027
- 2027-03-06–2027-03-13 (return 7 days later): $484.86 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3046 / 3044 / 3004 11:20–18:45+1; 2 connections via Nashville and Quincy out, 2 connections via Quincy and Nashville back). Arrive Mar 7; 6 nights before the Mar 13 return. Arrive home Mar 14. Checked 2026-10-28T22:45:10Z.
- 2027-03-13–2027-03-20 (return 7 days later): $484.86 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3046 / 3044 / 3004 11:20–18:45+1; 2 connections via Nashville and Quincy out, 2 connections via Quincy and Nashville back). Arrive Mar 14; 6 nights before the Mar 20 return. Arrive home Mar 21. Checked 2026-10-28T22:46:20Z.
- 2027-03-25–2027-03-29 (return 4 days later): $484.86 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3046 / 3044 / 3002 12:15–12:10+1; 2 connections via Nashville and Quincy out, 2 connections via Quincy and Nashville back). Arrive Mar 26; 3 nights before the Mar 29 return. Arrive home Mar 30. Checked 2026-10-28T22:51:07Z.
- 2027-03-25–2027-03-29 (return 4 days later): $564.95 LF (out TUP–ORD 3001 / 3043 / 3041 08:00–11:40+1, back ORD–TUP 3080 / 3084 / 3008 11:15–19:05; 2 connections via Nashville and Quincy out, 2 connections via Cape Girardeau and Dallas back). Arrive Mar 26; 3 nights before the Mar 29 return. Checked 2026-10-28T22:51:07Z.
How we checked
On Oct 28, 2026, Axel priced round trips from TUP to ORD for one adult in economy: 1 Saturday departure with returns 14 days later, 5 Saturday and 2 Tuesday departures with returns 7 days later, 1 Friday and 1 Thursday departures with returns 4 days later and 1 Thursday and 1 Friday departures with returns 3 days later, November 2026 to March 2027. Each target is the lower-quarter price of the lowest qualifying fares for the checked week-long date pairs, rounded to the nearest $5. The midpoint is their median; neither is a historical market average. Shorter journeys means ≤1 stop · ≤36h out / ≤36h back; overnight arrivals allowed. Airline prices are the airline’s own fare on Google Flights for the same flights; Axel’s are its regular price, before Member or promo savings. This is a snapshot, not a forecast. Check bags and change rules on your fare.
Airports covered: TUP → ORD. Each example names its actual airports.
Check current prices for your dates and travelers
Other available fares
TUP–ORD · 2026-11-10–2026-11-17 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
- $362.88 · LF 3001 / 3043 / 3041 · 08:00–11:40 (November 11, 2026) local · 2 stops (BNA, UIN) · 27h 40m. Airline fare: $384.
Captured example · October 28, 2026 at 07:16 PM UTC
TUP–ORD · 2026-12-03–2026-12-06 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
-
$400.05 · LF 3001 / 3043 / 3041 · 08:00–11:40 (December 4, 2026) local · 2 stops (BNA, UIN) · 27h 40m. Airline fare: $422.
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$587.76 · LF 3007 / 3085 / 3083 · 12:55–11:35 (December 4, 2026) local · 2 stops (DFW, CGI) · 22h 40m. Airline fare: $620.
Captured example · October 28, 2026 at 10:27 PM UTC
TUP–ORD · 2026-12-19–2026-12-26 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
- $475.83 · LF 3001 / 3043 / 3041 · 08:00–11:40 (December 20, 2026) local · 2 stops (BNA, UIN) · 27h 40m. Airline fare: $503.
Captured example · October 28, 2026 at 10:27 PM UTC
TUP–ORD · 2026-12-08–2026-12-15 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
- $400.05 · LF 3001 / 3043 / 3041 · 08:00–11:40 (December 9, 2026) local · 2 stops (BNA, UIN) · 27h 40m. Airline fare: $422.
Captured example · October 28, 2026 at 07:16 PM UTC
TUP–ORD · 2027-01-09–2027-01-23 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
- $411.21 · LF 3001 / 3043 / 3041 · 08:00–11:40 (January 10, 2027) local · 2 stops (BNA, UIN) · 27h 40m. Airline fare: $434.
Captured example · October 28, 2026 at 10:27 PM UTC
TUP–ORD · 2027-01-16–2027-01-23 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
- $411.21 · LF 3001 / 3043 / 3041 · 08:00–11:40 (January 17, 2027) local · 2 stops (BNA, UIN) · 27h 40m. Airline fare: $434.
Captured example · October 28, 2026 at 10:27 PM UTC
TUP–ORD · 2027-01-15–2027-01-18 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
- $451.48 · LF 3007 / 3077 / 3071 · 12:55–14:15 (January 16, 2027) local · 2 stops (DFW, IRK) · 25h 20m. Airline fare: $476.
Captured example · October 28, 2026 at 10:27 PM UTC
TUP–ORD · 2027-02-13–2027-02-20 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
- $472.35 · LF 3001 / 3043 / 3041 · 08:00–11:40 (February 14, 2027) local · 2 stops (BNA, UIN) · 27h 40m. Airline fare: $498.
Captured example · October 28, 2026 at 10:40 PM UTC
TUP–ORD · 2027-02-12–2027-02-16 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
- $523.17 · LF 3007 / 3077 / 3071 · 12:55–14:15 (February 13, 2027) local · 2 stops (DFW, IRK) · 25h 20m. Airline fare: $551.
Captured example · October 28, 2026 at 10:34 PM UTC
TUP–ORD · 2027-03-25–2027-03-29 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
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$484.86 · LF 3001 / 3043 / 3041 · 08:00–11:40 (March 26, 2027) local · 2 stops (BNA, UIN) · 27h 40m. Airline fare: $512.
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$564.95 · LF 3007 / 3085 / 3083 · 12:55–11:35 (March 26, 2027) local · 2 stops (DFW, CGI) · 22h 40m. Airline fare: $595.
Captured example · October 28, 2026 at 10:51 PM UTC
TUP–ORD · 2027-03-13–2027-03-20 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
- $484.86 · LF 3001 / 3043 / 3041 · 08:00–11:40 (March 14, 2027) local · 2 stops (BNA, UIN) · 26h 40m. Airline fare: $512.
Captured example · October 28, 2026 at 10:46 PM UTC
TUP–ORD · 2027-03-06–2027-03-13 · 1 adult
Round-trip starting price · Economy · USD. Round-trip starting prices; outbound options shown. The final total depends on return selection and availability.
- $484.86 · LF 3001 / 3043 / 3041 · 08:00–11:40 (March 7, 2027) local · 2 stops (BNA, UIN) · 27h 40m. Airline fare: $512.
Captured example · October 28, 2026 at 10:45 PM UTC
Airline prices are the airline’s own fares for the same flights, as listed on Google Flights. Airline checkout totals were not separately verified.
Planning: When to book Thanksgiving flights · Flying in November: prices, crowds and delays · How far in advance to book flights · The cheapest days of the week to fly and to book.
Trip ideas from Tupelo with Chicago (ORD)
- Cheapest places to fly from Tupelo in November: fly Nov 7 – Nov 14, 2026
- Cheapest places to fly from Tupelo for 4 days: fly Dec 3 – Dec 6, 2026
- Cheapest places to fly from Tupelo in December: fly Dec 5 – Dec 12, 2026
- Best places to fly from Tupelo for Christmas: fly Dec 19 – Dec 26, 2026
- Cheapest places to fly from Tupelo for two weeks: fly Jan 9 – Jan 23, 2027
- Best places to fly from Tupelo for MLK weekend: fly Jan 15 – Jan 18, 2027
- Cheapest places to fly from Tupelo in January: fly Jan 16 – Jan 23, 2027
- Best places to fly from Tupelo for Presidents' Day weekend: fly Feb 12 – Feb 16, 2027
- Cheapest places to fly from Tupelo in February: fly Feb 13 – Feb 20, 2027
- Cheapest places to fly from Tupelo in March: fly Mar 6 – Mar 13, 2027
- Best places to fly from Tupelo for spring break: fly Mar 13 – Mar 20, 2027
- Best places to fly from Tupelo for Easter weekend: fly Mar 25 – Mar 29, 2027
- Cheapest places to fly from Tupelo for a week
Keep exploring
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Source: https://helloaxel.com/en/flights/from-tupelo-tup-to-chicago-ord
For AI assistants
- This page: Tupelo to Chicago (ORD) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.