Chicago from Hartford, 16 – 18 Oct: £1,202 for two, all in
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The verdict
Our verdict
Worth it, if
- 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
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.
Worth it if you can live with an overnight connection: $1,594 for two, which is the Frontier flights at $800 plus Club Quarters Hotel Central Loop, Chicago at $794, taxes and fees included. The trip runs Oct 16–18, 2026, for 2 nights. You leave Hartford Friday at 3:16 PM, make 1 stop and land at O'Hare Saturday at 7:51 AM, and resort fees, a checked bag and spending money are not in the total.
The total, before you go
£1,202 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £603 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights, two guests, taxes in | £598 |
| The total, before you go | £1,202 |
| Hold luggage each, return (not in the total) | about £181 |
£51 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £45 each way per bag on Frontier, £181 for two return); a resort fee, if the hotel has one, is collected at the desk. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
£302 per person, return
£603 for two, taxes and fees included · Frontier · 1 stop · 17h 35m
Out Fri, Oct 16, 3:16 PM – Sat, Oct 17, 7:51 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £302 | 1 stop | 17h 35m |
| American | £436 | nonstop | 2h 48m |
| JetBlue | £406 | 1 stop | 14h 2m |
Prices checked 14 Oct 2026, 11:14 GMT-4. Prices change; the binding price is the one on the booking site.
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Tweak this trip
Why now
At $400 per person, Frontier is $68 below the typical fare on this route, or 15% under it. When we checked, $1,594 for two covered the round-trip flights and 2 nights at Club Quarters Hotel Central Loop, Chicago, taxes and fees included. Fares for these dates ran from $400 to $733 per person. What you give up is time, because the lower fare connects overnight. If that's a dealbreaker, American flies nonstop in 2h 48m for $579 per person, or $1,158 for two for the flights. The weather mostly works out: Friday's 84% chance of rain at 57°F falls while you're traveling, Saturday is overcast at 58°F and Sunday looks clear at 65°F. That gives you a museum day and then a day for the river. Prices move, so check the live price before you go.
The kind of trip this is
This is a city weekend built on architecture, art and food, with live blues after dark. It suits a couple or two friends who like to walk, eat well and fit a museum in between meals. The pace is quick, with one full Saturday and a Sunday. Pick a couple of anchors, like the river cruise and the Art Institute, and spend the rest of the time on deep-dish and wandering the neighborhoods.
Weather in Chicago, 16 – 18 Oct
Highs 57–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 57 °F | 49 °F | 84% |
| Sat 17 Oct | 58 °F | 46 °F | 18% |
| Sun 18 Oct | 65 °F | 50 °F | 1% |
Where to stay in Chicago
Club Quarters Hotel Central Loop, Chicago is the best-value pick and the one in the total. It's $794 for the 2 nights ($397 a night) for a Club Room, with 4 stars and an 8.2 from 5,335 reviews. Central Loop Hotel is the budget pick at the same $794 for the stay, with 4 stars and an 8.1 from 3,685 reviews, in a Double Room. Moxy Chicago Downtown is the top rated, at 8.9 from 389 reviews. It costs $904 for the stay ($452 a night) for a Queen Room in River North, which has galleries, steakhouses and the city's nightlife core. The two hotels in The Loop put architecture, theaters and Millennium Park right outside the door. All three are room only, and none of them offers free cancellation.
Club Quarters Hotel Central Loop, Chicago
£598 for 2 nights, two guests · £299 a night
See roomsMoxy Chicago Downtown
£681 for 2 nights, two guests · £341 a night
See roomsCentral Loop Hotel
£598 for 2 nights, two guests · £299 a night
See roomsAll hotels in Chicago for these dates
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Where in Chicago
- The Loop: Architecture, theatres and Millennium Park at your doorstep.
- Magnificent Mile / Streeterville: Shopping on Michigan Avenue and lakefront hotels.
- River North: Galleries, steakhouses and the city's nightlife core.
- West Loop: Converted warehouses with the top restaurant row on Randolph Street.
- Lincoln Park: Leafy neighbourhood with a free zoo and lakefront beaches.
What to do in Chicago
- Take the Chicago Architecture Foundation river cruise on clear Sunday
- See the Bean and the fountains in Millennium Park, steps from the Loop hotels
- Spend overcast Saturday at the Art Institute of Chicago
- Eat deep-dish at Lou Malnati's or Pequod's
- Hear live blues at Kingston Mines on Saturday night
- Catch a Cubs game at Wrigley Field if the schedule lines up
Also worth it
- Visit the Art Institute of Chicago
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Getting there and around
| Airports in Hartford | Bradley International (BDL) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 17h 35m (1 stop) |
| Distance | 769 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £603 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | £598 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,593 |
Flights and hotel are the prices we found; spending is a planning estimate for an upscale destination, per person per day times two.
Price history: Hartford to Chicago
| Per person | |
|---|---|
| This trip | £302 per person |
| Lowest in the last 30 days | £295 (13 Oct 2026) |
| Typical price, last 60 days | £353 |
| Price checks | 12 |
Good to know
- Passport: no passport needed for travellers from the United States: a government photo ID is enough for Chicago.
- Currency: US dollar (USD).
- No passport needed and it's US dollars, and Chicago is 1 hour behind Hartford.
- Frontier leaves Bradley International (BDL) Friday at 3:16 PM, makes 1 stop and lands at Chicago O'Hare International (ORD) Saturday at 7:51 AM.
- Chicago also has Chicago Midway International (MDW), and Hartford to Chicago is 769 miles.
- All three hotels are room only, with no breakfast included, and none offers free cancellation.
- Resort fees, a checked bag and spending money are not in the $1,594 total.
Questions readers ask
Is it worth it?
Worth it if the overnight connection doesn't bother you. The fare is $400 per person, which is $68 below the typical fare on this route, and the Loop hotel scores 8.2. If you'd rather arrive Friday afternoon, the American nonstop is $579 per person.
How much is the whole trip for two?
It's $1,594 for two, all in: $800 for the Frontier flights and $794 for 2 nights at Club Quarters Hotel Central Loop, Chicago, taxes and fees included, as we found it. Resort fees, a checked bag and spending money are not included.
Is there a nonstop?
Yes. American leaves Friday at 1:00 PM and lands at 2:48 PM, which is 2h 48m, for $579 per person, or $1,158 for two for the flights. The Frontier fare in our total has 1 stop and takes 17h 35m.
What is the weather like?
Friday shows an 84% chance of rain and a high of 57°F, though you'll be traveling. Saturday is overcast at 58°F with an 18% chance of rain. Sunday looks clear at 65°F with a 1% chance.
Is 2 nights enough?
With the Frontier fare, you really get Saturday and Sunday, because you land at 7:51 AM Saturday. That's enough for the river cruise, the Art Institute, Millennium Park, deep-dish and a night of blues.
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
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