Chicago from Hartford, Oct 23–25: round trip from $426
Round trip from Hartford to Chicago is $426 per person ($852 for two) for 2 nights, Oct 23–25, 2026, on Frontier (F9) with one stop, not nonstop. Expect highs of 55–71°F with a small chance of rain. The best-value hotel, Hilton Chicago in the Loop, is $522 for the 2-night stay.
The flight
$453 $426 per person, round trip
the typical fare on this route
$852 for two, taxes and fees included · Frontier · 1 stop · 35h 58m
Out Fri, Oct 23, 3:16 PM – Sat, Oct 24, 7:51 AM · back Sun, Oct 25, 6:58 PM – Mon, Oct 26, 2:21 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $426 | 1 stop | 35h 58m |
| United | $742 | nonstop | 5h 3m |
| JetBlue | $437 | 1 stop | 24h 22m |
Prices checked Oct 13, 2026, 1:14 AM EDT. Prices change; the binding price is the one on the booking site.
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Your trip for two
| For two | |
|---|---|
| Flights for two | $852 |
| Hilton Chicago, 2 nights | $522 |
| Trip total for two | $1,374 |
Regular: $1,428 You pay: $1,374 Saved: $54
the typical fare on this route.
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Why go now
At $426 per person round trip, this fare is $27 below the typical fare on this route, which was $453 across our earlier checks. That's 6% under, or $852 for two. Fares we saw for this weekend ran from $426 to $742 per person. Heads-up on timing: the $426 Frontier fare leaves Bradley at 3:16 PM Friday and reaches O'Hare at 7:51 AM Saturday, and the return lands Monday, Oct 26 at 2:21 PM. If you want Friday night in the city, JetBlue at $437 per person leaves at 6:25 AM and lands at 11:24 AM the same day. Late October brings highs from 71°F down to 55°F, mostly overcast, which suits museums, a river cruise and long deep-dish dinners.
The kind of trip this is
This is a city weekend built around food, architecture and live music. It suits a couple or two friends who like to walk a lot, eat well and end the night in a blues club. The pace is quick: two nights, a compact downtown, and most of the big sights within easy reach of the Loop. Pack a warm layer for the cooler, overcast days.
Weather in Chicago, Oct 23–25
Highs 55–71°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 71 °F | 57 °F | 23% |
| Sat, Oct 24 | 60 °F | 53 °F | 23% |
| Sun, Oct 25 | 55 °F | 48 °F | 31% |
Where to stay in Chicago
Two of the three picks are in the Loop, which puts architecture, theatres and Millennium Park at your doorstep, and one is in the South Loop. Hilton Chicago is the best value at $522 for 2 nights ($261 a night), a King Room with a 7.9 review score from 981 reviews, room only. citizenM Chicago Downtown is the top rated, 8.8 from 3,095 reviews, at $622 for the stay ($311 a night) for a high-floor King Room. Hampton Inn Chicago McCormick Place is the budget-tagged pick at $548 ($274 a night), scores 8.5 from 735 reviews and includes breakfast, with two queen beds. None of the three offered free cancellation when we checked. For a night out, River North is the city's nightlife core, with galleries and steakhouses.
Hilton Chicago
$522 for 2 nights, two guests · $261 a night
See roomscitizenM Chicago Downtown
$622 for 2 nights, two guests · $311 a night
See roomsHampton Inn Chicago McCormick Place
$548 for 2 nights, two guests · $274 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 to see the skyline from the water.
- See the Bean in Millennium Park, a short walk from the Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's, then compare notes.
- Spend overcast Sunday morning inside the Art Institute of Chicago.
- Hear live blues at Kingston Mines on Saturday night.
Also worth it
- See the Bean and the fountains in Millennium Park
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
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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 | 35h 58m (1 stop) |
| Distance | 769 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $852 |
| Hotel, 2 nights (Hilton Chicago) | $522 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,894 |
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 | $426 per person |
| Lowest in the last 30 days | $392 (Oct 13, 2026) |
| Typical price, last 60 days | $453 |
| Price checks | 8 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed: it's a domestic trip, paid in US dollars.
- Chicago is 1 hour behind Hartford.
- The $426 outbound takes 35h 58m with one stop, including an overnight connection.
- Hilton Chicago and citizenM Chicago Downtown are room only; the Hampton Inn includes breakfast. None offered free cancellation.
- Prices are all-in, taxes and fees included, as found when we checked; they can change before you book.
Questions readers ask
How much is the flight?
$426 per person round trip, $852 for two, on Frontier (F9) with one stop, all-in when we checked. A nonstop United fare was $742 per person, and JetBlue with one stop was $437.
Is 2 nights enough?
On the $426 fare you land at O'Hare at 7:51 AM Saturday, so you get Saturday and most of Sunday before the 6:58 PM flight home. That covers a river cruise, Millennium Park, the Art Institute and a blues night. The JetBlue fare at $437 gets you in Friday at 11:24 AM.
What is the weather like?
The forecast shows Friday at 71°F with drizzle, Saturday at 60°F and overcast, Sunday at 55°F and overcast. Lows run 48°F to 57°F, and rain chances sit between 23% and 31%. Bring a jacket.
Do I need a passport?
No. You fly domestic from Bradley International (BDL) to Chicago O'Hare International (ORD), and you'll pay in US dollars.
What does the whole weekend cost for two?
Our budget comes to $1,894: $852 in flights, $522 at Hilton Chicago for 2 nights and $520 for spending, which works out to $130 per person per day.
When do I get home?
The return leaves Sunday at 6:58 PM and lands Monday, Oct 26 at 2:21 PM, so plan on Monday morning off.
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