Chicago from Savannah, Oct 23–25: $1,814 for two, all in
The verdict
Our verdict
Worth it, because
- Nonstop on United, 2h 36m
- $127 per person below the typical fare on this route
- Highs 58–70°F, little rain expected
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 Savannah to Chicago cost $563 per person for Oct 23–25, 2026 when we checked, $127 below the typical fare on this route. Three places to stay start at $297 a night for the 2-night stay. The total, before you go: $1,720 for two, flights and Hilton Chicago with taxes and fees. Prices move; every link below shows the live price.
The total, before you go
$1,814 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $1,126 |
| Hilton Chicago, 2 nights, two guests, taxes in | $594 |
| Resort fee, collected at the desk | $94 |
| The total, before you go | $1,814 |
| A checked bag each, round trip (not in the total) | about $160 |
$127 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); the resort fee is counted above. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
$563 per person, round trip
$1,126 for two, taxes and fees included · United · nonstop · 2h 36m
Out Fri, Oct 23, 8:53 AM – Fri, Oct 23, 10:29 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| United | $563 | nonstop | 2h 36m |
| American. Operated by Republic Airways as American Eagle | $563 | nonstop | 2h 42m |
| United. Operated by Republic Airways DBA United Express | $563 | nonstop | 2h 39m |
Prices checked Oct 15, 2026, 2:47 AM 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: The only nonstop of the four, 2h 36m, at $563 per person, which is $130 (19%) under the typical $693.
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 58–70°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 70 °F | 56 °F | 13% |
| Sat, Oct 24 | 64 °F | 58 °F | 18% |
| Sun, Oct 25 | 58 °F | 49 °F | 23% |
Where to stay in Chicago
Hilton Chicago
$594 for 2 nights, two guests · $297 a night
See roomsSwissotel Chicago
$717 for 2 nights, two guests · $359 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 Savannah | Savannah/Hilton Head International (SAV) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 2h 36m nonstop |
| Distance | 767 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $1,126 |
| Hotel, 2 nights (Hilton Chicago) | $594 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,240 |
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: Savannah to Chicago
| Per person | |
|---|---|
| This trip | $563 per person |
| Lowest in the last 30 days | $553 (Oct 12, 2026) |
| Typical price, last 60 days | $690 |
| Price checks | 9 |
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 Savannah cost?
About $2,240 for two: $1,126 in flights, $594 for the hotel and $520 for food, getting around and tickets.
What is the weather like in Chicago Oct 23–25?
Highs 58–70°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 Savannah to Chicago?
2h 36m nonstop on United, on the fare we found.
Is $563 a good price for Savannah to Chicago?
It is 18% below the typical $690 per person we see on this route, which is why it made the list.
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Nov 14–21, 2026 · 7 nights
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Oct 16–18, 2026 · 2 nights
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The weekend after · from Savannah43% below typical
New York City
Oct 30–Nov 1, 2026 · 2 nights
- Delta nonstop, 2h 10m, landing at 9:30 AM Friday
- $259 per person, $200 below the typical fare on this route
- Westgate New York Grand Central: 8.4 from 1,752 reviews, free cancellation
$1,781 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
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Delta. Operated by Endeavor Air DBA Delta Connection · nonstop · 2h 10m
The catch: The total leaves out a checked bag, about $140 for two, and Saturday's normals point to drizzle with a high near 63°F.
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Nov 14–21, 2026 · 7 nights
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- Highs of 55–66°F, mild weather for a week of red-rock hiking
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$2,648 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights $934 + hotel $1,490 + resort fee $224, taxes in · a checked bag each adds about $160
United · with a stop · 9h 53m
The catch: One stop makes the flight out 9h 53m, our weather data shows drizzle or rain on three days, and a checked bag is about $160 for two.
Worth it if you want a walkable week of food and bay views in a jacket; skip it if you need a nonstop or warm sun.
All trips from Savannah · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
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Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License