Hartford to Chicago: what the flight costs
In the last 60 days we checked this route 14 times. The typical return was £354 per person and the lowest £295, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | £295 |
| Typical (median) | £354 |
| Price checks, 60 days | 14 |
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Trips we picked on this route
Just found · from HartfordWorth it, if
Chicago
23 – 25 Oct 2026 · 2 nights
- £20 per person below the typical fare on this route
- Highs 55–71°F, a small chance of rain
- No passport needed
£1,036 for two · 2 nights · flights, hotel, taxes & fees
Flights £642 + hotel £393, taxes in · a checked bag each adds about £181
Frontier · with a stop · 35h 58m
The catch: Not nonstop: a stop on the way, 35h 58m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Just found · from HartfordWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- Frontier fare is $400 per person, $68 below the typical fare
- Club Quarters in the Loop scores 8.2 from 5,335 reviews
- Sunday looks clear, 65°F with a 1% chance of rain
£1,202 for two · 2 nights · flights, hotel, taxes & fees
Flights £603 + hotel £598, taxes in · a checked bag each adds about £181
Frontier · with a stop · 17h 35m
The catch: The Frontier fare has 1 stop and takes 17h 35m overnight, landing Saturday at 7:51 AM, so you'll barely use your first hotel night.
Worth it if you can sleep through a connection and want a museum-and-deep-dish weekend for less; skip it if Friday night in Chicago matters to you.
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| 15 Oct 2026 | 30 Oct – 1 Nov 2026 | £354 | B6 | with a stop | 12h 50m | Kiwi.com |
| 15 Oct 2026 | 23 – 25 Oct 2026 | £390 | B6 | with a stop | 13h 15m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £406 | B6 | with a stop | 14h 2m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £302 | Frontier | with a stop | 17h 35m | Google Flights |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £358 | F9 + B6 | with a stop | 17h 35m | Kiwi.com |
| 13 Oct 2026 | 16 – 18 Oct 2026 | £353 | F9 + B6 | with a stop | 17h 35m | Kiwi.com |
| 13 Oct 2026 | 23 – 25 Oct 2026 | £321 | F9 | with a stop | 35h 58m | Kiwi.com |
| 13 Oct 2026 | 23 – 25 Oct 2026 | £329 | B6 + F9 | with a stop | 5h 59m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £415 | F9 + B6 | with a stop | 25h 30m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £295 | Frontier | with a stop | 17h 35m | Google Flights |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £422 | F9 | with a stop | 35h 24m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £295 | Frontier | with a stop | 17h 35m | Google Flights |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £353 | F9 + B6 | with a stop | 17h 35m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £355 | F9 + B6 | with a stop | 17h 35m | Kiwi.com |
About Chicago
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Chicago from every city: when to go, where to stay, what to do
Questions about Hartford to Chicago
What does a return from Hartford to Chicago usually cost?
Over the last 60 days the typical price we found was £354 per person, taxes and fees included, across 14 checks; the lowest was £295.
When is the best time to fly from Hartford to Chicago?
Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake
Do I need a passport to fly from Hartford to Chicago?
No passport needed for travellers from the United States: a government photo ID is enough for Chicago.
Prices converted from US dollars at the rate of 15 Oct 2026.