Chicago from Albany, Oct 23–25: $1,628 for two, all in
The verdict
Our verdict
Worth it, because
- Nonstop on United, 2h 33m
- $157 per person below the typical fare on this route
- Lowest in 30 days on this route
The catch: The best-value hotel is rated 7.9; a better one costs more.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Nonstop flights on United from Albany to Chicago cost $537 per person for Oct 23–25, 2026 when we checked, $157 below the typical fare on this route. Three places to stay start at $277 a night for the 2-night stay. The total, before you go: $1,628 for two, flights and Hilton Chicago with taxes and fees. Prices move; every link below shows the live price.
The total, before you go
$1,628 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $1,074 |
| Hilton Chicago, 2 nights, two guests, taxes in | $554 |
| The total, before you go | $1,628 |
| A checked bag each, round trip (not in the total) | about $160 |
$157 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $40 each way per bag on United, $160 for two round trip); 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
$537 per person, round trip
$1,074 for two, taxes and fees included · United · nonstop · 2h 33m
Out Fri, Oct 23, 6:20 AM – Fri, Oct 23, 7:53 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| United | $537 | nonstop | 2h 33m |
| American. Operated by SkyWest Airlines as American Eagle | $557 | nonstop | 2h 43m |
| United | $537 | nonstop | 2h 34m |
Prices checked Oct 14, 2026, 1:13 PM EDT. Prices change; the binding price is the one on the booking site.
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
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Why Chicago
Why we picked it: Chicago is the best value we priced for the weekend: $537 round trip, nonstop, 23% under the typical price.
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Weather in Chicago, Oct 23–25
Highs 56–75°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 61 °F | 52 °F | 19% |
| Sat, Oct 24 | 75 °F | 54 °F | 23% |
| Sun, Oct 25 | 56 °F | 47 °F | 16% |
Where to stay in Chicago
Hilton Chicago
$554 for 2 nights, two guests · $277 a night
See roomsSable At Navy Pier Chicago, Curio Collection By Hilton
$768 for 2 nights, two guests · $384 a night
See roomsAloft by Marriott Chicago Mag Mile
$597 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
Signature experiences
- Take the Chicago Architecture Foundation river cruise
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
- Hear live blues at Kingston Mines
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Getting there and around
| Airports in Albany | Albany International (ALB) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 2h 33m nonstop |
| Distance | 710 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $1,074 |
| Hotel, 2 nights (Hilton Chicago) | $554 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,148 |
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: Albany to Chicago
| Per person | |
|---|---|
| This trip | $537 per person |
| Lowest in the last 30 days | $537 (Oct 14, 2026) |
| Typical price, last 60 days | $694 |
| Price checks | 10 |
Good to know
- Passport: no passport needed for travelers from the United States: a government photo ID is enough for Chicago.
- Currency: US dollar (USD).
Questions readers ask
How much does 2 nights in Chicago from Albany cost?
About $2,148 for two: $1,074 in flights, $554 for the hotel and $520 for food, getting around and tickets.
What is the weather like in Chicago Oct 23–25?
Highs 56–75°F, little rain expected
Do I need a passport for Chicago?
No. No passport needed for travelers from the United States: a government photo ID is enough for Chicago.
How long is the flight from Albany to Chicago?
2h 33m nonstop on United, on the fare we found.
Is $537 a good price for Albany to Chicago?
It is 23% below the typical $694 per person we see on this route, which is why it made the list.
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Nov 13–18, 2026 · 5 nights
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- Hilton Vacation Club Ridge on Sedona: 8.8 from 868 reviews, free cancellation
- Hiking weather, with highs of 56–66°F and lows near 40°F
$1,619 for two · 5 nights · flights, hotel, taxes, fees & the resort fee
Flights $727 + hotel $842 + resort fee $50, taxes in · a checked bag each adds about $200
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The catch: The trip out has 2 stops and takes 35h 5m, landing Saturday, Nov 14 at 8:54 PM, and a checked bag is about $200 for two.
Worth it if you can trade a long first day for red-rock hiking weather; skip it if you can't give up most of a day to travel.
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Dec 3–7, 2026 · 4 nights
- $318 per person, $12 below the $330 typical fare
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- Typical highs of 77–82°F and lows near 65°F
$1,554 for two · 4 nights · flights, hotel, taxes, fees & the resort fee
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American. Operated by Piedmont Airlines as American Eagle · with a stop · 6h 9m
The catch: There's no nonstop: the flight has one stop and takes 6h 9m, and a checked bag, about $160 for two, isn't in the total.
Worth it if you want a warm, easy beach long weekend; skip it if you need a nonstop or full sun every single day.
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Just found · from AlbanyWorth it, if
Fort Lauderdale
Dec 11–15, 2026 · 4 nights
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- $327 per person, $71 below the highest fare we saw
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$1,248 for two · 4 nights · flights, hotel, taxes & fees
Flights $654 + hotel $594, taxes in · a checked bag each adds about $160
American · with a stop · 5h 29m
The catch: One stop on American, 5h 29m, landing at 12:33 AM; a checked bag is about $160 for two, and resort fees aren't in the total.
Worth it if you want warm beach days for a fair price and don't mind a late arrival; skip it if you need a nonstop.
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Oct 23–25, 2026 · 2 nights
- Nonstop on Allegiant, 2h 20m, landing at 10:47 PM Friday
- Friday and Saturday highs of 76–77°F, rain chances of 4% and 8%
- Sonesta Nashville Airport scores 8.8 from 977 reviews, free cancellation
$1,533 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $1,094 + hotel $380 + resort fee $59, taxes in · a checked bag each adds about $200
Allegiant · nonstop · 2h 20m
The catch: The fare is $15 per person above typical, and a checked bag is about $200 for two that isn't in the total.
Worth it if you want a music-and-food weekend with a late Friday nonstop; skip it if you'd rather wait for a fare closer to $532.
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Washington, D.C.
Oct 30–Nov 1, 2026 · 2 nights
- 1h 35m nonstop from Albany to Reagan Washington National
- $349 per person, $378 below the typical fare on this route
- citizenM Washington DC Georgetown: 9 from 276 reviews, free cancellation
$1,032 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $698 + hotel $294 + resort fee $40, taxes in · a checked bag each adds about $160
American. Operated by PSA Airlines as American Eagle · nonstop · 1h 35m
The catch: The lowest nonstop leaves Albany at 5:05 AM, and a checked bag is about $160 for two, which isn't in the total.
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Nov 14–21, 2026 · 7 nights
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United. Operated by Commuteair DBA United Express · with a stop · 5h 24m
The catch: One stop on United Express makes it 5h 24m, landing at 12:59 AM; a checked bag is about $160 for two and isn't in the total.
Worth it if you can handle a late-night landing for a fare under typical; skip it if you'd rather pay $720 for two for the 3h 5m Southwest nonstop.
Just found · from AlbanyWorth it, if
Sedona
Nov 13–18, 2026 · 5 nights
- $364 per person, $19 below the typical fare on this route
- Hilton Vacation Club Ridge on Sedona: 8.8 from 868 reviews, free cancellation
- Hiking weather, with highs of 56–66°F and lows near 40°F
$1,619 for two · 5 nights · flights, hotel, taxes, fees & the resort fee
Flights $727 + hotel $842 + resort fee $50, taxes in · a checked bag each adds about $200
G4 + F9 · with a stop · 35h 5m
The catch: The trip out has 2 stops and takes 35h 5m, landing Saturday, Nov 14 at 8:54 PM, and a checked bag is about $200 for two.
Worth it if you can trade a long first day for red-rock hiking weather; skip it if you can't give up most of a day to travel.
All trips from Albany · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
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Image credits
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License