# Chicago (MDW) to Boston (BOS), Jan 21, 2027: round trips from $283, one way from $155

Chicago (MDW) to Boston (BOS), Jan 21, 2027: round trips from $283, one way from $155 on Axel, checked Nov 13, 2026. Lowest published fares: $283 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 21–27, 2027; $155 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 21, 2027; 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

**Prices by return date:** match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

**Date links** open published trip details for exploration. **Price links** open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price checked |
| --- | --- | --- | --- | ---: | --- |
| [2027-01-21 · one way](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/one-way) | Southwest Airlines | WN2902 | 19:35:00→22:55:00 2h 20m nonstop | [Axel-exclusive $155](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/trip/one-way/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.) | Nov 13, 2026 |
| [2027-01-21 · one way](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/one-way) | Delta Air Lines | DL5469 + DL2558 | 10:24:00→17:01:00 5h 37m 1 stop via MSP | [Axel-exclusive $205](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/trip/one-way/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-22](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-22) | Southwest Airlines | WN2902 / WN816 | 19:35:00→22:55:00 2h 20m nonstop · 18:30:00→20:15:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-22-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-01-22.WN.0.WN816.) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-22](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-22) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-22-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-01-22.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-23](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-23) | Southwest Airlines | WN2902 / WN2939 | 19:35:00→22:55:00 2h 20m nonstop · 12:20:00→14:05:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-23-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-01-23.WN.0.WN2939.) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-23](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-23) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-23-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-01-23.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-24](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-24) | Southwest Airlines | WN2902 / WN816 | 19:35:00→22:55:00 2h 20m nonstop · 18:30:00→20:15:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-24-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-01-24.WN.0.WN816.) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-24](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-24) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-24-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-01-24.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-25](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-25) | Southwest Airlines | WN2902 / WN816 | 19:35:00→22:55:00 2h 20m nonstop · 17:55:00→19:40:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-25-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-01-25.WN.0.WN816.) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-25](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-25) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-25-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-01-25.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-26](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-26) | Southwest Airlines | WN2902 / WN816 | 19:35:00→22:55:00 2h 20m nonstop · 17:55:00→19:40:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-26-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-01-26.WN.0.WN816.) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-26](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-26) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-26-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-01-26.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-27](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-27) | Southwest Airlines | WN2902 / WN819 + WN287 | 19:35:00→22:55:00 2h 20m nonstop · 05:35:00→12:05:00 7h 30m 1 stop via STL | [Axel-exclusive $283](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-27-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-01-27.WN.1.WN819-WN287.STL) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-27](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-27) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-27-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-01-27.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-28](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-28) | Southwest Airlines | WN2902 / WN816 | 19:35:00→22:55:00 2h 20m nonstop · 17:55:00→19:40:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-28-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-01-28.WN.0.WN816.) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-28](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-28) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-28-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-01-28.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-29](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-29) | Southwest Airlines | WN2902 / WN816 | 19:35:00→22:55:00 2h 20m nonstop · 18:30:00→20:15:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-29-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-01-29.WN.0.WN816.) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-29](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-29) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-29-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-01-29.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-30](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-30) | Southwest Airlines | WN2902 / WN2939 | 19:35:00→22:55:00 2h 20m nonstop · 12:20:00→14:05:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-30-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-01-30.WN.0.WN2939.) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-30](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-30) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-30-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-01-30.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-31](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-31) | Southwest Airlines | WN2902 / WN816 | 19:35:00→22:55:00 2h 20m nonstop · 18:30:00→20:15:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-31-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-01-31.WN.0.WN816.) | Nov 13, 2026 |
| [2027-01-21 → 2027-01-31](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/jan-31) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/january-31-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-01-31.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-02-01](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/feb-1) | Southwest Airlines | WN2902 / WN816 | 19:35:00→22:55:00 2h 20m nonstop · 17:55:00→19:40:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/february-1-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-02-01.WN.0.WN816.) | Nov 13, 2026 |
| [2027-01-21 → 2027-02-01](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/feb-1) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/february-1-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-02-01.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-02-02](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/feb-2) | Southwest Airlines | WN2902 / WN816 | 19:35:00→22:55:00 2h 20m nonstop · 17:55:00→19:40:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/february-2-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-02-02.WN.0.WN816.) | Nov 13, 2026 |
| [2027-01-21 → 2027-02-02](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/feb-2) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/february-2-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-02-02.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-02-03](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/feb-3) | Southwest Airlines | WN2902 / WN819 + WN287 | 19:35:00→22:55:00 2h 20m nonstop · 05:35:00→12:05:00 7h 30m 1 stop via STL | [Axel-exclusive $283](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/february-3-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-02-03.WN.1.WN819-WN287.STL) | Nov 13, 2026 |
| [2027-01-21 → 2027-02-03](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/feb-3) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/february-3-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-02-03.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |
| [2027-01-21 → 2027-02-04](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/feb-4) | Southwest Airlines | WN2902 / WN816 | 19:35:00→22:55:00 2h 20m nonstop · 17:55:00→19:40:00 2h 45m nonstop | [Axel-exclusive $290](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/february-4-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.WN.0.WN2902.%7EBOS-MDW.2027-02-04.WN.0.WN816.) | Nov 13, 2026 |
| [2027-01-21 → 2027-02-04](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21/feb-4) | Delta Air Lines | DL5469 + DL2558 / DL2222 + DL4677 | 10:24:00→17:01:00 5h 37m 1 stop via MSP · 13:04:00→18:01:00 5h 57m 1 stop via DTW | [Axel-exclusive $390](https://helloaxel.com/en/f/start/from/mdw/to/bos/depart/january-21-2027/return/february-4-2027/adults/1/cabin/economy?example_flight=MDW-BOS.2027-01-21.DL.1.DL5469-DL2558.MSP%7EBOS-MDW.2027-02-04.DL.1.DL2222-DL4677.DTW) | Nov 13, 2026 |

### Hotels in Boston for these trips

**Hotels:** under a trip, hotels in Boston for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

- Hotels in Boston for these nights (Jan 21–22, 2027 · 1 night · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $111 a night](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-01-22/2-adults) · 4★ [Harborside Inn Of Boston, $132 a night](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-01-22/2-adults) · 5★ [The Liberty, a Marriott Luxury Collection Hotel, Boston, $309 a night](https://helloaxel.com/en/hotels/boston/the-liberty-a-marriott-luxury-collection-hotel-boston-1059981/2027-01-21/2027-01-22/2-adults)
- Hotels in Boston for these nights (Jan 21–23, 2027 · 2 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $112 a night, $224 for 2 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-01-23/2-adults) · 4★ [Harborside Inn Of Boston, $135 a night, $269 for 2 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-01-23/2-adults) · 5★ [InterContinental Boston by IHG, $290 a night, $580 for 2 nights](https://helloaxel.com/en/hotels/boston/intercontinental-boston-by-ihg-1051774/2027-01-21/2027-01-23/2-adults)
- Hotels in Boston for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $112 a night, $337 for 3 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-01-24/2-adults) · 4★ [Harborside Inn Of Boston, $134 a night, $401 for 3 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-01-24/2-adults) · 5★ [InterContinental Boston by IHG, $285 a night, $856 for 3 nights](https://helloaxel.com/en/hotels/boston/intercontinental-boston-by-ihg-1051774/2027-01-21/2027-01-24/2-adults)
- Hotels in Boston for these nights (Jan 21–25, 2027 · 4 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $441 for 4 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-01-25/2-adults) · 4★ [Harborside Inn Of Boston, $134 a night, $537 for 4 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-01-25/2-adults) · 5★ [InterContinental Boston by IHG, $279 a night, $1,114 for 4 nights](https://helloaxel.com/en/hotels/boston/intercontinental-boston-by-ihg-1051774/2027-01-21/2027-01-25/2-adults)
- Hotels in Boston for these nights (Jan 21–26, 2027 · 5 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $109 a night, $547 for 5 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-01-26/2-adults) · 4★ [Harborside Inn Of Boston, $135 a night, $676 for 5 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-01-26/2-adults) · 5★ [Omni Boston Hotel at the Seaport, $297 a night, $1,483 for 5 nights](https://helloaxel.com/en/hotels/boston/omni-boston-hotel-at-the-seaport-1427259/2027-01-21/2027-01-26/2-adults)
- Hotels in Boston for these nights (Jan 21–27, 2027 · 6 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $662 for 6 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-01-27/2-adults) · 4★ [Harborside Inn Of Boston, $136 a night, $813 for 6 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-01-27/2-adults) · 5★ [Omni Boston Hotel at the Seaport, $301 a night, $1,807 for 6 nights](https://helloaxel.com/en/hotels/boston/omni-boston-hotel-at-the-seaport-1427259/2027-01-21/2027-01-27/2-adults)
- Hotels in Boston for these nights (Jan 21–28, 2027 · 7 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $773 for 7 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-01-28/2-adults) · 4★ [Harborside Inn Of Boston, $136 a night, $949 for 7 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-01-28/2-adults) · 5★ [Omni Boston Hotel at the Seaport, $306 a night, $2,142 for 7 nights](https://helloaxel.com/en/hotels/boston/omni-boston-hotel-at-the-seaport-1427259/2027-01-21/2027-01-28/2-adults)
- Hotels in Boston for these nights (Jan 21–29, 2027 · 8 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $109 a night, $875 for 8 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-01-29/2-adults) · 4★ [Harborside Inn Of Boston, $136 a night, $1,086 for 8 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-01-29/2-adults) · 5★ [Omni Boston Hotel at the Seaport, $311 a night, $2,488 for 8 nights](https://helloaxel.com/en/hotels/boston/omni-boston-hotel-at-the-seaport-1427259/2027-01-21/2027-01-29/2-adults)
- Hotels in Boston for these nights (Jan 21–30, 2027 · 9 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $992 for 9 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-01-30/2-adults) · 4★ [Harborside Inn Of Boston, $136 a night, $1,222 for 9 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-01-30/2-adults) · 5★ [Omni Boston Hotel at the Seaport, $310 a night, $2,788 for 9 nights](https://helloaxel.com/en/hotels/boston/omni-boston-hotel-at-the-seaport-1427259/2027-01-21/2027-01-30/2-adults)
- Hotels in Boston for these nights (Jan 21–31, 2027 · 10 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $1,102 for 10 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-01-31/2-adults) · 4★ [Harborside Inn Of Boston, $136 a night, $1,358 for 10 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-01-31/2-adults) · 5★ [Omni Boston Hotel at the Seaport, $305 a night, $3,052 for 10 nights](https://helloaxel.com/en/hotels/boston/omni-boston-hotel-at-the-seaport-1427259/2027-01-21/2027-01-31/2-adults)
- Hotels in Boston for these nights (Jan 21 – Feb 1, 2027 · 11 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $1,206 for 11 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-02-01/2-adults) · 4★ [Harborside Inn Of Boston, $136 a night, $1,492 for 11 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-02-01/2-adults) · 5★ [Omni Boston Hotel at the Seaport, $300 a night, $3,297 for 11 nights](https://helloaxel.com/en/hotels/boston/omni-boston-hotel-at-the-seaport-1427259/2027-01-21/2027-02-01/2-adults)
- Hotels in Boston for these nights (Jan 21 – Feb 2, 2027 · 12 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $1,325 for 12 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-02-02/2-adults) · 4★ [Harborside Inn Of Boston, $136 a night, $1,632 for 12 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-02-02/2-adults) · 5★ [Omni Boston Hotel at the Seaport, $299 a night, $3,583 for 12 nights](https://helloaxel.com/en/hotels/boston/omni-boston-hotel-at-the-seaport-1427259/2027-01-21/2027-02-02/2-adults)
- Hotels in Boston for these nights (Jan 21 – Feb 3, 2027 · 13 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $111 a night, $1,443 for 13 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-02-03/2-adults) · 4★ [Harborside Inn Of Boston, $135 a night, $1,760 for 13 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-02-03/2-adults) · 5★ [Omni Boston Hotel at the Seaport, $296 a night, $3,854 for 13 nights](https://helloaxel.com/en/hotels/boston/omni-boston-hotel-at-the-seaport-1427259/2027-01-21/2027-02-03/2-adults)
- Hotels in Boston for these nights (Jan 21 – Feb 4, 2027 · 14 nights · 2 adults, 1 room): 3★ [Holiday Inn Boston - Cambridge Area by IHG, $111 a night, $1,558 for 14 nights](https://helloaxel.com/en/hotels/boston/holiday-inn-boston-cambridge-area-by-ihg-1255780/2027-01-21/2027-02-04/2-adults) · 4★ [Harborside Inn Of Boston, $136 a night, $1,897 for 14 nights](https://helloaxel.com/en/hotels/boston/harborside-inn-of-boston-1083049/2027-01-21/2027-02-04/2-adults) · 5★ [Omni Boston Hotel at the Seaport, $302 a night, $4,221 for 14 nights](https://helloaxel.com/en/hotels/boston/omni-boston-hotel-at-the-seaport-1427259/2027-01-21/2027-02-04/2-adults)

[All hotels in Boston](https://helloaxel.com/en/hotels/destinations/boston)

[Route overview: Chicago to Boston (BOS) flight deals](/en/flights/from-chicago-to-boston-bos)

### 2027-01-21 · one way · Axel-exclusive $155

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.

### 2027-01-21 · one way · Axel-exclusive $205

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.

### 2027-01-21 → 2027-01-22 · Axel-exclusive $290

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.
- Southwest Airlines WN816: BOS 2027-01-22 18:30:00 → MDW 2027-01-22 20:15:00; nonstop; 165 minutes. Local airport times.

### 2027-01-21 → 2027-01-22 · Axel-exclusive $390

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.
- Delta Air Lines DL2222 / DL4677: BOS 2027-01-22 13:04:00 → MDW 2027-01-22 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  - DL2222: BOS 2027-01-22 13:04:00 → DTW 2027-01-22 15:19:00; layover at DTW: 141 minutes.
  - DL4677: DTW 2027-01-22 17:40:00 → MDW 2027-01-22 18:01:00.

### 2027-01-21 → 2027-01-23 · Axel-exclusive $290

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.
- Southwest Airlines WN2939: BOS 2027-01-23 12:20:00 → MDW 2027-01-23 14:05:00; nonstop; 165 minutes. Local airport times.

### 2027-01-21 → 2027-01-23 · Axel-exclusive $390

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.
- Delta Air Lines DL2222 / DL4677: BOS 2027-01-23 13:04:00 → MDW 2027-01-23 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  - DL2222: BOS 2027-01-23 13:04:00 → DTW 2027-01-23 15:19:00; layover at DTW: 141 minutes.
  - DL4677: DTW 2027-01-23 17:40:00 → MDW 2027-01-23 18:01:00.

### 2027-01-21 → 2027-01-24 · Axel-exclusive $290

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.
- Southwest Airlines WN816: BOS 2027-01-24 18:30:00 → MDW 2027-01-24 20:15:00; nonstop; 165 minutes. Local airport times.

### 2027-01-21 → 2027-01-24 · Axel-exclusive $390

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.
- Delta Air Lines DL2222 / DL4677: BOS 2027-01-24 13:04:00 → MDW 2027-01-24 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  - DL2222: BOS 2027-01-24 13:04:00 → DTW 2027-01-24 15:19:00; layover at DTW: 141 minutes.
  - DL4677: DTW 2027-01-24 17:40:00 → MDW 2027-01-24 18:01:00.

### 2027-01-21 → 2027-01-25 · Axel-exclusive $290

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.
- Southwest Airlines WN816: BOS 2027-01-25 17:55:00 → MDW 2027-01-25 19:40:00; nonstop; 165 minutes. Local airport times.

### 2027-01-21 → 2027-01-25 · Axel-exclusive $390

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.
- Delta Air Lines DL2222 / DL4677: BOS 2027-01-25 13:04:00 → MDW 2027-01-25 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  - DL2222: BOS 2027-01-25 13:04:00 → DTW 2027-01-25 15:19:00; layover at DTW: 141 minutes.
  - DL4677: DTW 2027-01-25 17:40:00 → MDW 2027-01-25 18:01:00.

### 2027-01-21 → 2027-01-27 · Axel-exclusive $283

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.
- Southwest Airlines WN819 / WN287: BOS 2027-01-27 05:35:00 → MDW 2027-01-27 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  - WN819: BOS 2027-01-27 05:35:00 → STL 2027-01-27 07:40:00; layover at STL: 195 minutes.
  - WN287: STL 2027-01-27 10:55:00 → MDW 2027-01-27 12:05:00.

### 2027-01-21 → 2027-01-27 · Axel-exclusive $390

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.
- Delta Air Lines DL2222 / DL4677: BOS 2027-01-27 13:04:00 → MDW 2027-01-27 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  - DL2222: BOS 2027-01-27 13:04:00 → DTW 2027-01-27 15:19:00; layover at DTW: 141 minutes.
  - DL4677: DTW 2027-01-27 17:40:00 → MDW 2027-01-27 18:01:00.

### 2027-01-21 → 2027-01-28 · Axel-exclusive $290

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.
- Southwest Airlines WN816: BOS 2027-01-28 17:55:00 → MDW 2027-01-28 19:40:00; nonstop; 165 minutes. Local airport times.

### 2027-01-21 → 2027-01-28 · Axel-exclusive $390

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.
- Delta Air Lines DL2222 / DL4677: BOS 2027-01-28 13:04:00 → MDW 2027-01-28 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  - DL2222: BOS 2027-01-28 13:04:00 → DTW 2027-01-28 15:19:00; layover at DTW: 141 minutes.
  - DL4677: DTW 2027-01-28 17:40:00 → MDW 2027-01-28 18:01:00.

### 2027-01-21 → 2027-01-29 · Axel-exclusive $290

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.
- Southwest Airlines WN816: BOS 2027-01-29 18:30:00 → MDW 2027-01-29 20:15:00; nonstop; 165 minutes. Local airport times.

### 2027-01-21 → 2027-01-29 · Axel-exclusive $390

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.
- Delta Air Lines DL2222 / DL4677: BOS 2027-01-29 13:04:00 → MDW 2027-01-29 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  - DL2222: BOS 2027-01-29 13:04:00 → DTW 2027-01-29 15:19:00; layover at DTW: 141 minutes.
  - DL4677: DTW 2027-01-29 17:40:00 → MDW 2027-01-29 18:01:00.

### 2027-01-21 → 2027-01-31 · Axel-exclusive $290

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.
- Southwest Airlines WN816: BOS 2027-01-31 18:30:00 → MDW 2027-01-31 20:15:00; nonstop; 165 minutes. Local airport times.

### 2027-01-21 → 2027-01-31 · Axel-exclusive $390

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.
- Delta Air Lines DL2222 / DL4677: BOS 2027-01-31 13:04:00 → MDW 2027-01-31 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  - DL2222: BOS 2027-01-31 13:04:00 → DTW 2027-01-31 15:19:00; layover at DTW: 141 minutes.
  - DL4677: DTW 2027-01-31 17:40:00 → MDW 2027-01-31 18:01:00.

### 2027-01-21 → 2027-02-01 · Axel-exclusive $290

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.
- Southwest Airlines WN816: BOS 2027-02-01 17:55:00 → MDW 2027-02-01 19:40:00; nonstop; 165 minutes. Local airport times.

### 2027-01-21 → 2027-02-01 · Axel-exclusive $390

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.
- Delta Air Lines DL2222 / DL4677: BOS 2027-02-01 13:04:00 → MDW 2027-02-01 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  - DL2222: BOS 2027-02-01 13:04:00 → DTW 2027-02-01 15:19:00; layover at DTW: 141 minutes.
  - DL4677: DTW 2027-02-01 17:40:00 → MDW 2027-02-01 18:01:00.

### 2027-01-21 → 2027-02-02 · Axel-exclusive $290

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.
- Southwest Airlines WN816: BOS 2027-02-02 17:55:00 → MDW 2027-02-02 19:40:00; nonstop; 165 minutes. Local airport times.

### 2027-01-21 → 2027-02-02 · Axel-exclusive $390

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.
- Delta Air Lines DL2222 / DL4677: BOS 2027-02-02 13:04:00 → MDW 2027-02-02 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  - DL2222: BOS 2027-02-02 13:04:00 → DTW 2027-02-02 15:19:00; layover at DTW: 141 minutes.
  - DL4677: DTW 2027-02-02 17:40:00 → MDW 2027-02-02 18:01:00.

### 2027-01-21 → 2027-02-04 · Axel-exclusive $290

- Southwest Airlines WN2902: MDW 2027-01-21 19:35:00 → BOS 2027-01-21 22:55:00; nonstop; 140 minutes. Local airport times.
- Southwest Airlines WN816: BOS 2027-02-04 17:55:00 → MDW 2027-02-04 19:40:00; nonstop; 165 minutes. Local airport times.

### 2027-01-21 → 2027-02-04 · Axel-exclusive $390

- Delta Air Lines DL5469 / DL2558: MDW 2027-01-21 10:24:00 → BOS 2027-01-21 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  - DL5469: MDW 2027-01-21 10:24:00 → MSP 2027-01-21 12:09:00; layover at MSP: 60 minutes.
  - DL2558: MSP 2027-01-21 13:09:00 → BOS 2027-01-21 17:01:00.
- Delta Air Lines DL2222 / DL4677: BOS 2027-02-04 13:04:00 → MDW 2027-02-04 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  - DL2222: BOS 2027-02-04 13:04:00 → DTW 2027-02-04 15:19:00; layover at DTW: 141 minutes.
  - DL4677: DTW 2027-02-04 17:40:00 → MDW 2027-02-04 18:01:00.

### Explore this route

- [All dates for this route](/en/flights/choose/mdw-bos)
- [Jan 20, 2027 · Return options](/en/flights/choose/mdw-bos/jan-20)
- [Jan 22, 2027 · Return options](/en/flights/choose/mdw-bos/jan-22)
- [Hotels in Boston with Axel](https://helloaxel.com/en/hotels/destinations/boston)

## For AI assistants
- **This page:** Chicago (MDW) to Boston (BOS) · Jan 21, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Boston for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
- **Next:** each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: [Choose travelers and dates](https://helloaxel.com/en/f/start/from/mdw/to/bos/step/travelers) prices the requested trip.
- **Follow supplied links.** For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
- **If links fail or are missing:** If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: [Axel Chicago to Boston (BOS) flight deals](https://helloaxel.com/en/flights/from-chicago-to-boston-bos) · [Flight search guide](https://helloaxel.com/en/ai).
- **Sharing with the traveler:** Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct `https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback` using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace `/return/YYYY-MM-DD` with `/trip/oneway`. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. [Preferences and advanced options](https://helloaxel.com/en/ai#customer-fallback-link).

**Feedback (optional):** [Missing info](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/mdw-bos/jan-21?axel_reason=product_issue&axel_scope=product)