Cheapest places to fly from Tupelo for 4 days (Dec 3–6, 2026)
No published fare for Thu Dec 3 – Sun Dec 6, 2026 from Tupelo yet; the lowest published fares for the months ahead follow.
Four days is a nonstop and a place you can be in by lunch: a big city or a beach within about three hours' flight. Thursday to Sunday is the cheaper shape; Friday to Monday is the busier one.
No nonstop seen to Chicago on the dates searched recently. No recent searches for Nashville and Dallas.
Where to fly from Tupelo for 4 days: fares for A December long weekend (Dec 3 to 6) and A March long weekend (Mar 4 to 7) 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 A December long weekend (Dec 3 – Dec 6, 2026) and A March long weekend (Mar 4 – Mar 7, 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.
Next: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.
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★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $194 total · 5★ Sofitel Chicago Magnificent Mile, $724 total
- Hotels in Chicago for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $194 total · 5★ Sofitel Chicago Magnificent Mile, $679 total
- Hotels in Chicago for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $520 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $357 total · 5★ Sofitel Chicago Magnificent Mile, $1,504 total
- Hotels in Chicago for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $216 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $726 total
- Hotels in Chicago for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $224 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $71 total · 5★ Sofitel Chicago Magnificent Mile, $722 total
- Hotels in Chicago for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $542 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $374 total · 5★ Sofitel Chicago Magnificent Mile, $1,613 total
- Hotels in Chicago for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $219 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $213 total · 5★ Sofitel Chicago Magnificent Mile, $1,045 total
- Hotels in Chicago for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $216 total · 4★ Freehand Chicago, $230 total · 5★ Nobu Hotel Chicago, $1,093 total
- Hotels in Chicago for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $528 total · 4★ Freehand Chicago, $514 total · 5★ Nobu Hotel Chicago, $2,588 total
- Hotels in Chicago for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ Freehand Chicago, $229 total · 5★ Sofitel Chicago Magnificent Mile, $787 total
- Hotels in Chicago for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $204 total · 5★ Sofitel Chicago Magnificent Mile, $791 total
- Hotels in Chicago for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $616 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $192 total · 5★ Sofitel Chicago Magnificent Mile, $1,851 total
- Hotels in Chicago for these nights (Feb 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $295 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $112 total · 5★ Sofitel Chicago Magnificent Mile, $794 total
- Hotels in Chicago for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $294 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $112 total · 5★ Sofitel Chicago Magnificent Mile, $794 total
- Hotels in Chicago for these nights (Feb 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $642 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $375 total · 5★ Sofitel Chicago Magnificent Mile, $1,822 total
- Hotels in Chicago for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $379 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $279 total · 5★ Sofitel Chicago Magnificent Mile, $777 total
- Hotels in Chicago for these nights (Feb 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $324 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $112 total · 5★ Sofitel Chicago Magnificent Mile, $773 total
- Hotels in Chicago for these nights (Feb 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $642 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $216 total · 5★ Sofitel Chicago Magnificent Mile, $1,813 total
- Hotels in Chicago for these nights (Mar 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $360 total · 4★ Freehand Chicago, $293 total · 5★ Sofitel Chicago Magnificent Mile, $1,029 total
- Hotels in Chicago for these nights (Mar 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $854 total · 4★ Freehand Chicago, $654 total · 5★ Sofitel Chicago Magnificent Mile, $2,406 total
- Hotels in Chicago for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $562 total · 4★ Freehand Chicago, $383 total · 5★ Sofitel Chicago Magnificent Mile, $1,394 total
- Hotels in Chicago for these nights (Apr 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $537 total · 4★ Freehand Chicago, $374 total · 5★ Nobu Hotel Chicago, $1,199 total
- Hotels in Chicago for these nights (Apr 17–24, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,032 total · 4★ Freehand Chicago, $832 total · 5★ Nobu Hotel Chicago, $3,023 total
- 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 · for Easter weekend · in November · in December · in January · in February · in March · 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 nonstop seen | No matching fare saved | Dec 3 – Dec 6, 2026 (suggested) | Search these dates |
| Nashville (BNA) | Nashville's honky-tonks and hot chicken | No matching fare saved | Dec 3 – Dec 6, 2026 (suggested) | Search these dates | |
| Dallas (DFW) | Dallas and Fort Worth's museums, stockyards and barbecue | No matching fare saved | Dec 3 – Dec 6, 2026 (suggested) | Search these dates |
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: Cheapest places to fly from Tupelo for 4 days. Where to fly from Tupelo for 4 days: Cancun, Las Vegas, Orlando, Honolulu, San Jose Cabo and Puerto Vallarta and more, priced for A December long weekend (Dec 3 to 6) and A March long weekend (Mar 4 to 7), 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.