Best places to fly from Tupelo for Easter weekend 2027
Easter Sunday 2027 is Sunday, Mar 28. No published fare for Thu Mar 25 – Mon Mar 29, 2027 from Tupelo yet; the lowest published fares for the months ahead follow.
Easter weekend is a short peak: the beaches and theme parks fill for the week either side, while cities and the countryside are quiet and often in their first good weather of the year. Thursday out and Monday back is the shape; Saturday out is the cheaper one.
Where to fly from Tupelo for Easter weekend: fares for Easter weekend 2027 (Mar 25 to 29) to Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, with the nonstops first. Pick a destination to see every date, or search your own dates in one tap.
AI assistants: For research, follow complete supplied links unchanged.
Saved round trips for Easter weekend 2027 (Mar 25 – Mar 29, 2027).
Flights for the months ahead
Lowest published fares for the months ahead: $510 round trip, Axel-exclusive, LF, 2 stops, Nov 19–22, 2026; $275 one way, Axel-exclusive, LF, 2 stops, Dec 1, 2026; 72 priced flights on 72 exact dates, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
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Tupelo (TUP) to Chicago (ORD): November 2026
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026 | LF | Up to 2 stops each way | Axel-exclusive $510.00 |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026 | LF | Up to 2 stops each way | Axel-exclusive $510.00 |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026 | LF | Up to 2 stops each way | Axel-exclusive $573.75 |
| Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026 | LF | Up to 2 stops each way | Axel-exclusive $343.75 |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026 | LF | Up to 2 stops each way | Axel-exclusive $637.50 |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 | LF | Up to 2 stops each way | Axel-exclusive $637.50 |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 | LF | Up to 2 stops each way | Axel-exclusive $637.50 |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 | LF | Up to 2 stops each way | Axel-exclusive $573.75 |
Tupelo (TUP) to Chicago (ORD): December 2026
Tupelo (TUP) to Chicago (ORD): January 2027
Tupelo (TUP) to Chicago (ORD): February 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 | LF | Up to 2 stops each way | Axel-exclusive $275.00 |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027 | LF | Up to 2 stops each way | Axel-exclusive $510.00 |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027 | LF | Up to 2 stops each way | Axel-exclusive $510.00 |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027 | LF | Up to 2 stops each way | Axel-exclusive $510.00 |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 | LF | Up to 2 stops each way | Axel-exclusive $510.00 |
| Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027 | LF | Up to 2 stops each way | Axel-exclusive $510.00 |
| Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027 | LF | Up to 2 stops each way | Axel-exclusive $510.00 |
Tupelo (TUP) to Chicago (ORD): March 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027 | LF | Up to 2 stops each way | Axel-exclusive $510.00 |
| Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027 | LF | Up to 2 stops each way | Axel-exclusive $535.50 |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027 | LF | Up to 2 stops each way | Axel-exclusive $588.50 |
Tupelo (TUP) to Chicago (ORD): April 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
| Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
Tupelo (TUP) to Chicago (ORD): May 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
| May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
| May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027 | LF | Up to 2 stops each way | Axel-exclusive $616.00 |
Tupelo (TUP) to Chicago (ORD): June 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
| Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
Tupelo (TUP) to Chicago (ORD): July 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027 | LF | Up to 2 stops each way | Axel-exclusive $602.00 |
| Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
| Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
Tupelo (TUP) to Chicago (ORD): August 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
| Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
Tupelo (TUP) to Chicago (ORD): September 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027 | LF | Up to 2 stops each way | Axel-exclusive $616.00 |
| Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027 | LF | Up to 2 stops each way | Axel-exclusive $588.00 |
| Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
| Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027 | LF | Up to 2 stops each way | Axel-exclusive $560.00 |
Hotels in Chicago for these trips
Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.
- Hotels in Chicago for these nights (Nov 19–22, 2026 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $480 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $206 total · 5★ Nobu Hotel Chicago, $1,410 total
- Hotels in Chicago for these nights (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $472 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $206 total · 5★ Nobu Hotel Chicago, $1,262 total
- Hotels in Chicago for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $873 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $395 total · 5★ Nobu Hotel Chicago, $2,423 total
- Hotels in Chicago for these nights (Nov 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $625 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $328 total · 5★ Sofitel Chicago Magnificent Mile, $1,266 total
- Hotels in Chicago for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $438 total · 4★ Freehand Chicago, $258 total · 5★ Sofitel Chicago Magnificent Mile, $824 total
- Hotels in Chicago for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $424 total · 4★ Freehand Chicago, $259 total · 5★ Sofitel Chicago Magnificent Mile, $918 total
- Hotels in Chicago for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $810 total · 4★ Freehand Chicago, $590 total · 5★ Sofitel Chicago Magnificent Mile, $2,057 total
- Hotels in Chicago for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $369 total · 4★ Freehand Chicago, $246 total · 5★ Sofitel Chicago Magnificent Mile, $848 total
- Hotels in Chicago for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $345 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $220 total · 5★ Sofitel Chicago Magnificent Mile, $841 total
- Hotels in Chicago for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $735 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $281 total · 5★ Nobu Hotel Chicago, $2,855 total
- Hotels in Chicago for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $348 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $209 total · 5★ Sofitel Chicago Magnificent Mile, $985 total
- Hotels in Chicago for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ Congress Plaza Hotel, $349 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $157 total · 5★ Sofitel Chicago Magnificent Mile, $960 total
- Hotels in Chicago for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $681 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $233 total · 5★ Sofitel Chicago Magnificent Mile, $1,663 total
- Hotels in Chicago for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $325 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $157 total · 5★ Sofitel Chicago Magnificent Mile, $726 total
- Hotels in Chicago for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $316 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $157 total · 5★ Sofitel Chicago Magnificent Mile, $718 total
- Hotels in Chicago for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $712 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $274 total · 5★ Sofitel Chicago Magnificent Mile, $1,687 total
- Hotels in Chicago for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $477 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $209 total · 5★ Sofitel Chicago Magnificent Mile, $1,173 total
- Hotels in Chicago for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $289 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $171 total · 5★ Sofitel Chicago Magnificent Mile, $688 total
- Hotels in Chicago for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $277 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $171 total · 5★ Sofitel Chicago Magnificent Mile, $708 total
- Hotels in Chicago for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $833 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $512 total · 5★ Sofitel Chicago Magnificent Mile, $1,886 total
- Hotels in Chicago for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $424 total · 4★ Freehand Chicago, $335 total · 5★ Sofitel Chicago Magnificent Mile, $873 total
- Hotels in Chicago for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $408 total · 4★ Freehand Chicago, $332 total · 5★ Sofitel Chicago Magnificent Mile, $874 total
- Hotels in Chicago for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $128 total · 5★ Sofitel Chicago Magnificent Mile, $671 total
- Hotels in Chicago for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $543 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $315 total · 5★ Sofitel Chicago Magnificent Mile, $1,620 total
- Hotels in Chicago for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Feb 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Feb 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Feb 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Feb 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Mar 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Mar 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Apr 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Apr 17–24, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (May 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (May 15–22, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jun 11–14, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jun 12–19, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jul 2–6, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jul 9–12, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Jul 10–17, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Aug 6–9, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Aug 7–14, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Sep 3–6, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Sep 4–11, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Sep 24–27, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
- Hotels in Chicago for these nights (Sep 25 – Oct 2, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ Waldorf Astoria Chicago
Route overview: Tupelo to Chicago (ORD) flight deals
2026-11-19 → 2026-11-22 · Axel-exclusive $510.00
- LF LF3001 / LF3043 / LF3041: TUP 2026-11-19 08:00:00 → ORD 2026-11-20 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2026-11-19 08:00:00 → BNA 2026-11-19 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2026-11-20 08:00:00 → UIN 2026-11-20 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2026-11-20 09:55:00 → ORD 2026-11-20 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2026-11-22 12:15:00 → TUP 2026-11-22 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2026-11-22 12:15:00 → UIN 2026-11-22 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2026-11-22 14:40:00 → BNA 2026-11-22 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2026-11-22 17:40:00 → TUP 2026-11-22 18:45:00.
2026-11-24 · one way · Axel-exclusive $343.75
- LF LF3001 / LF3043 / LF3041: TUP 2026-11-24 08:00:00 → ORD 2026-11-25 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2026-11-24 08:00:00 → BNA 2026-11-24 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2026-11-25 08:00:00 → UIN 2026-11-25 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2026-11-25 09:55:00 → ORD 2026-11-25 11:40:00.
2026-11-28 → 2026-12-05 · Axel-exclusive $573.75
- LF LF3001 / LF3043 / LF3041: TUP 2026-11-28 08:00:00 → ORD 2026-11-29 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2026-11-28 08:00:00 → BNA 2026-11-28 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2026-11-29 08:00:00 → UIN 2026-11-29 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2026-11-29 09:55:00 → ORD 2026-11-29 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2026-12-05 12:15:00 → TUP 2026-12-05 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2026-12-05 12:15:00 → UIN 2026-12-05 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2026-12-05 14:40:00 → BNA 2026-12-05 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2026-12-05 17:40:00 → TUP 2026-12-05 18:45:00.
2026-12-12 → 2026-12-19 · Axel-exclusive $573.75
- LF LF3001 / LF3043 / LF3041: TUP 2026-12-12 08:00:00 → ORD 2026-12-13 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2026-12-12 08:00:00 → BNA 2026-12-12 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2026-12-13 08:00:00 → UIN 2026-12-13 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2026-12-13 09:55:00 → ORD 2026-12-13 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2026-12-19 12:15:00 → TUP 2026-12-19 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2026-12-19 12:15:00 → UIN 2026-12-19 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2026-12-19 14:40:00 → BNA 2026-12-19 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2026-12-19 17:40:00 → TUP 2026-12-19 18:45:00.
2026-12-25 → 2026-12-28 · Axel-exclusive $637.50
- LF LF3001 / LF3043 / LF3041: TUP 2026-12-25 08:00:00 → ORD 2026-12-26 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2026-12-25 08:00:00 → BNA 2026-12-25 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2026-12-26 08:00:00 → UIN 2026-12-26 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2026-12-26 09:55:00 → ORD 2026-12-26 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2026-12-28 12:15:00 → TUP 2026-12-28 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2026-12-28 12:15:00 → UIN 2026-12-28 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2026-12-28 14:40:00 → BNA 2026-12-28 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2026-12-28 17:40:00 → TUP 2026-12-28 18:45:00.
2027-01-07 → 2027-01-10 · Axel-exclusive $510.00
- LF LF3001 / LF3043 / LF3041: TUP 2027-01-07 08:00:00 → ORD 2027-01-08 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2027-01-07 08:00:00 → BNA 2027-01-07 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2027-01-08 08:00:00 → UIN 2027-01-08 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2027-01-08 09:55:00 → ORD 2027-01-08 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2027-01-10 12:15:00 → TUP 2027-01-10 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2027-01-10 12:15:00 → UIN 2027-01-10 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2027-01-10 14:40:00 → BNA 2027-01-10 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2027-01-10 17:40:00 → TUP 2027-01-10 18:45:00.
2027-01-21 → 2027-01-24 · Axel-exclusive $510.00
- LF LF3001 / LF3043 / LF3041: TUP 2027-01-21 08:00:00 → ORD 2027-01-22 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2027-01-21 08:00:00 → BNA 2027-01-21 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2027-01-22 08:00:00 → UIN 2027-01-22 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2027-01-22 09:55:00 → ORD 2027-01-22 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2027-01-24 12:15:00 → TUP 2027-01-24 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2027-01-24 12:15:00 → UIN 2027-01-24 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2027-01-24 14:40:00 → BNA 2027-01-24 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2027-01-24 17:40:00 → TUP 2027-01-24 18:45:00.
2027-02-04 → 2027-02-07 · Axel-exclusive $510.00
- LF LF3001 / LF3043 / LF3041: TUP 2027-02-04 08:00:00 → ORD 2027-02-05 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2027-02-04 08:00:00 → BNA 2027-02-04 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2027-02-05 08:00:00 → UIN 2027-02-05 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2027-02-05 09:55:00 → ORD 2027-02-05 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2027-02-07 12:15:00 → TUP 2027-02-07 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2027-02-07 12:15:00 → UIN 2027-02-07 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2027-02-07 14:40:00 → BNA 2027-02-07 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2027-02-07 17:40:00 → TUP 2027-02-07 18:45:00.
2027-03-19 → 2027-03-22 · Axel-exclusive $510.00
- LF LF3001 / LF3043 / LF3041: TUP 2027-03-19 08:00:00 → ORD 2027-03-20 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2027-03-19 08:00:00 → BNA 2027-03-19 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2027-03-20 08:00:00 → UIN 2027-03-20 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2027-03-20 09:55:00 → ORD 2027-03-20 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2027-03-22 12:15:00 → TUP 2027-03-22 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2027-03-22 12:15:00 → UIN 2027-03-22 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2027-03-22 14:40:00 → BNA 2027-03-22 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2027-03-22 17:40:00 → TUP 2027-03-22 18:45:00.
2027-05-15 → 2027-05-22 · Axel-exclusive $560.00
- LF LF3001 / LF3043 / LF3041: TUP 2027-05-15 08:00:00 → ORD 2027-05-16 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2027-05-15 08:00:00 → BNA 2027-05-15 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2027-05-16 08:00:00 → UIN 2027-05-16 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2027-05-16 09:55:00 → ORD 2027-05-16 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2027-05-22 12:15:00 → TUP 2027-05-22 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2027-05-22 12:15:00 → UIN 2027-05-22 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2027-05-22 14:40:00 → BNA 2027-05-22 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2027-05-22 17:40:00 → TUP 2027-05-22 18:45:00.
2027-07-10 → 2027-07-17 · Axel-exclusive $560.00
- LF LF3001 / LF3043 / LF3041: TUP 2027-07-10 08:00:00 → ORD 2027-07-11 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2027-07-10 08:00:00 → BNA 2027-07-10 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2027-07-11 08:00:00 → UIN 2027-07-11 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2027-07-11 09:55:00 → ORD 2027-07-11 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2027-07-17 12:15:00 → TUP 2027-07-17 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2027-07-17 12:15:00 → UIN 2027-07-17 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2027-07-17 14:40:00 → BNA 2027-07-17 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2027-07-17 17:40:00 → TUP 2027-07-17 18:45:00.
2027-09-25 → 2027-10-02 · Axel-exclusive $560.00
- LF LF3001 / LF3043 / LF3041: TUP 2027-09-25 08:00:00 → ORD 2027-09-26 11:40:00; 2 stop(s) via BNA, UIN; 1660 minutes. Local airport times.
- LF3001: TUP 2027-09-25 08:00:00 → BNA 2027-09-25 09:05:00; layover at BNA: 1375 minutes.
- LF3043: BNA 2027-09-26 08:00:00 → UIN 2027-09-26 09:25:00; layover at UIN: 30 minutes.
- LF3041: UIN 2027-09-26 09:55:00 → ORD 2027-09-26 11:40:00.
- LF LF3046 / LF3044 / LF3004: ORD 2027-10-02 12:15:00 → TUP 2027-10-02 18:45:00; 2 stop(s) via UIN, BNA; 390 minutes. Local airport times.
- LF3046: ORD 2027-10-02 12:15:00 → UIN 2027-10-02 13:40:00; layover at UIN: 60 minutes.
- LF3044: UIN 2027-10-02 14:40:00 → BNA 2027-10-02 16:10:00; layover at BNA: 90 minutes.
- LF3004: BNA 2027-10-02 17:40:00 → TUP 2027-10-02 18:45:00.
More dates for this route
- Nov 19, 2026 · Return options
- Nov 27, 2026 · Return options
- Dec 8, 2026 · Return options
- Dec 19, 2026 · Return options
- Dec 29, 2026 · Return options
- Jan 8, 2027 · Return options
- Jan 19, 2027 · Return options
- Jan 30, 2027 · Return options
- Feb 19, 2027 · Return options
- May 14, 2027 · Return options
- Jul 9, 2027 · Return options
- Sep 25, 2027 · Return options
- Hotels in Chicago with Axel
More trip ideas from Tupelo
- Anywhere: for Christmas · for MLK weekend · for Presidents' Day weekend · for spring break · in November · in December · in January · in February · in March · for 4 days · for a week · for two weeks
Where to go from Tupelo
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Flights | Axel-exclusive | Dates | |
|---|---|---|---|---|---|
| Chicago (ORD) | Chicago's architecture, lakefront and deep-dish | No matching fare saved | Mar 25 – Mar 29, 2027 (suggested) | Search these dates | |
| Nashville (BNA) | Nashville's honky-tonks and hot chicken | No matching fare saved | Mar 25 – Mar 29, 2027 (suggested) | Search these dates | |
| Dallas (DFW) | Dallas and Fort Worth's museums, stockyards and barbecue | No matching fare saved | Mar 25 – Mar 29, 2027 (suggested) | Search these dates |
About these places
Facts checked October 27, 2026. Sources: OPM: federal holidays 2026 and 2027
Keep exploring
Hotels in Chicago with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Chicago has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Chicago: the 10 best neighborhoods, ranked · Chicago hotels where a family of four can share one room
Hotel details in Chicago: The Langham, Chicago 5★ · LondonHouse Chicago, Curio Collection by Hilton 4★ · The Peninsula Chicago 5★ · Hampton Inn Chicago West Loop Fulton Market Area 2★ · Waldorf Astoria Chicago 5★ from $398 a night in the next 30 days · All 200 hotels in Chicago
For AI assistants
- This page: Best places to fly from Tupelo for Easter weekend. Where to fly from Tupelo for Easter weekend: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, priced for Easter weekend 2027 (Mar 25 to 29), nonstop options first. The cheapest saved fare for each destination, and a link to search your own dates.
- 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.