Chicago from Savannah, 16 – 18 Oct: £1,203 for two, all in
This page’s text is in English for now; a translation is on its way.
The verdict
Our verdict
Worth it, if
- £103 per person below the typical fare on this route
- Lowest in 30 days on this route
- Highs 53–62°F, little rain expected
The catch: Not nonstop: a stop on the way, 5h 15m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
A round trip from Savannah to Chicago is $553 per person ($1,106 for two) for Oct 16–18, 2026, 2 nights, on American operated by PSA Airlines as American Eagle, with one stop. Expect highs of 53–62°F, with drizzle possible Friday and clear skies after that. The best-value hotel is $490 for the stay.
The total, before you go
£1,203 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £834 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights, two guests, taxes in | £369 |
| The total, before you go | £1,203 |
| Hold luggage each, return (not in the total) | about £121 |
£103 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £30 each way per bag on American, £121 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
£417 per person, return
£834 for two, taxes and fees included · American. Operated by PSA Airlines as American Eagle · 1 stop · 5h 15m
Out Fri, Oct 16, 6:50 AM – Fri, Oct 16, 11:05 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| American. Operated by PSA Airlines as American Eagle | £417 | 1 stop | 5h 15m |
| United. Operated by Republic Airways DBA United Express | £436 | nonstop | 2h 39m |
| American | £417 | 1 stop | 4h 28m |
Prices checked 12 Oct 2026, 14:48 GMT-4. 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
Tweak this trip
Why now
At $553 per person, or $1,106 for two, this fare is $137 below the typical fare on this route. That's 20% under the $690 median of our earlier checks, and it's the lowest fare we've seen here in 30 days. We checked 12 offers and they ran from $553 to $579 per person, so there isn't much spread between them. Mid-October is a good time for a city weekend in Chicago. Saturday looks clear with a high of 53°F, Sunday is clear at 62°F, and Friday could bring drizzle, which is a good excuse for a museum afternoon. It's a trip for walking the Loop, taking a river cruise and eating well. Prices are all-in, taxes and fees included, as found when we checked, and they can change before you book.
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, eat well and stay out late. The pace is quick but doable: land before lunch Friday, spend Saturday on the river and in museums, and keep Sunday for deep-dish and the lakefront parks. Pack a warm layer, because this is cool-weather Chicago, not beach season.
Weather in Chicago, 16 – 18 Oct
Highs 53–62°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 57 °F | 46 °F | 51% |
| Sat 17 Oct | 53 °F | 45 °F | 2% |
| Sun 18 Oct | 62 °F | 46 °F | 2% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best value: $490 for the two nights ($245 a night), with a 7.5 review score from 224 reviews. As the name says, it's by Midway Airport rather than downtown. Canopy By Hilton Chicago Central Loop is the top-rated pick, scoring 8.9 from 308 reviews, at $962 for the stay or $481 a night. Congress Plaza Hotel Chicago is the budget pick in the Loop: $750 total ($375 a night), a 7.1 score across 4,544 reviews, and it's the only one of the three with free cancellation. All three are room only. Staying in The Loop puts architecture, theatres and Millennium Park at your doorstep. For dinner, head to the West Loop and its restaurant row on Randolph Street.
Holiday Inn Chicago Midway Airport S by IHG
£369 for 2 nights, two guests · £185 a night
See roomsCanopy By Hilton Chicago Central Loop
£725 for 2 nights, two guests · £363 a night
See roomsCongress Plaza Hotel Chicago
£565 for 2 nights, two guests · £283 a night
See roomsAll hotels in Chicago for these dates
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
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 Saturday, forecast clear with a 2% chance of rain.
- See the Bean and the fountains in Millennium Park, right in The Loop.
- Visit the Art Institute of Chicago, a good plan if Friday's drizzle shows up.
- Eat deep-dish at Lou Malnati's or Pequod's, or try both and pick a side.
- Hear live blues at Kingston Mines for a Saturday night out.
Also worth it
- Catch a Cubs game at Wrigley Field
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
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 | 5h 15m (1 stop) |
| Distance | 767 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £834 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | £369 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,595 |
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 | £417 per person |
| Lowest in the last 30 days | £417 (12 Oct 2026) |
| Typical price, last 60 days | £520 |
| Price checks | 5 |
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: it's a domestic trip and you pay in US dollars.
- Chicago is 1 hour behind Savannah. The 767-mile outbound trip takes 5h 15m with one stop and lands at O'Hare (ORD).
- A United nonstop, operated by Republic Airways DBA United Express, was $579 per person: 6:10 AM to 7:49 AM, 2h 39m.
- Only Congress Plaza Hotel Chicago offers free cancellation, and none of the three hotels includes meals.
Questions readers ask
How much is the flight?
$553 per person round trip, or $1,106 for two, including taxes and fees as found when we checked. It's American, operated by PSA Airlines as American Eagle, with one stop, leaving SAV at 6:50 AM on Friday, Oct 16 and landing at 11:05 AM. Prices can change.
Do I need a passport?
No. Chicago is a domestic trip from Savannah, so a passport isn't required, and the currency is the US dollar.
What is the weather like?
Friday, Oct 16 has a high of 57°F and a low of 46°F, with drizzle and a 51% chance of rain. Saturday is clear with a high of 53°F. Sunday is clear with a high of 62°F. Lows run 45–46°F, so bring a jacket.
Is 2 nights enough?
For a first look, yes. You land at 11:05 AM Friday, which gives you Friday afternoon, all of Saturday and Sunday until your flight home. That's enough time for the river cruise, the Art Institute, Millennium Park and a deep-dish dinner. We didn't have return flight times.
What does the whole weekend cost for two?
By our estimate, $2,116 for two: $1,106 for flights, $490 at Holiday Inn Chicago Midway Airport S by IHG, and $520 for spending, which works out to $130 per person per day.
Also found for you
The newest finds from Savannah.
Just found · from SavannahLowest in 30 daysWorth it, if
New York City
14 – 21 Nov 2026 · 7 nights
- Nonstop Delta, 2h 12m, landing at 9:37 AM on Saturday
- $242 per person, $163 below the typical fare on this route
- Pod 51 scores 8.2 from 9,518 reviews, free cancellation
£1,743 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights £365 + hotel £1,207 + resort fee £171, taxes in · a checked bag each adds about £106
Delta. Operated by Endeavor Air DBA Delta Connection · nonstop · 2h 12m
The catch: At Pod 51 you get a bunk pod with a shared bathroom, highs run 45–55°F, and a checked bag is about $140 for two.
Worth it if you'll spend your days out at museums and shows and only need a bunk to sleep in; skip it if you want a private bathroom.
Tweak this trip
Just found · from SavannahWorth it, if
New York City
16 – 18 Oct 2026 · 2 nights
- $492 per person round trip, 6% under the typical fare
- Leave Savannah at 6:50 AM, land in New York by 11:28 AM
- San Carlos Hotel New York: 9.1 from 4,322 reviews, free cancellation
£1,403 for two · 2 nights · flights, hotel, taxes & fees
Flights £742 + hotel £661, taxes in · a checked bag each adds about £121
£23 per person below the typical fare on this route
American. Operated by PSA Airlines as American Eagle · with a stop · 4h 38m
The catch: Showers are forecast Friday at 86% and Saturday at 67%, and the low fare has one stop, 4h 38m on the way up.
Worth it if museums, a Broadway show and a rain jacket sound good to you; skip it if you want a dry weekend outdoors.
Tweak this trip
Just found · from SavannahLowest in 30 daysWorth it, if
Aruba
14 – 21 Nov 2026 · 7 nights
- £164 per person below the typical fare on this route
- Lowest in 30 days on this route
- Radisson Blu Aruba, rated 8.6 by 532 guests
£3,216 for two · 7 nights · flights, hotel, taxes & fees
Flights £959 + hotel £2,257, taxes in · a checked bag each adds about £121
American. Operated by Envoy Air as American Eagle · with a stop · 5h 16m
The catch: Not nonstop: a stop on the way, 5h 16m in all.
Worth it if you want sun, sand and a pool; skip it if you want a city to walk.
Tweak this trip
More trips
Next weekend · from Savannah18% below typical
Chicago
23 – 25 Oct 2026 · 2 nights
- Nonstop on United, 2h 36m
- £96 per person below the typical fare on this route
- Highs 58–70°F, little rain expected
£1,367 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £849 + hotel £448 + resort fee £71, taxes in · a checked bag each adds about £121
United · nonstop · 2h 36m
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.
The weekend after · from Savannah43% below typical
New York City
30 Oct – 1 Nov 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
£1,342 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £390 + hotel £840 + resort fee £112, taxes in · a checked bag each adds about £106
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.
Worth it if you want shows, museums and a fast-paced city weekend; skip it if you're after warm weather or a slow, quiet trip.
A week away · from SavannahLowest in 30 daysWorth it, if
Sedona
14 – 21 Nov 2026 · 7 nights
- $385 per person, $68 below the typical fare on this route
- Hilton Vacation Club Ridge on Sedona: 8.8 from 868 reviews, free cancellation
- Highs of 55–66°F, mild weather for a week of red-rock hiking
£1,522 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights £580 + hotel £889 + resort fee £53, taxes in · a checked bag each adds about £121
American · with a stop · 6h 35m
The catch: It's one stop and 6h 35m to Phoenix, then two hours north by road, and a checked bag is about $160 for two.
Worth it if you want a week of cool-weather hiking and spa time; skip it if you need a nonstop or warm sun.
Just found · from SavannahLowest in 30 daysWorth it, if
New York City
14 – 21 Nov 2026 · 7 nights
- Nonstop Delta, 2h 12m, landing at 9:37 AM on Saturday
- $242 per person, $163 below the typical fare on this route
- Pod 51 scores 8.2 from 9,518 reviews, free cancellation
£1,743 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights £365 + hotel £1,207 + resort fee £171, taxes in · a checked bag each adds about £106
Delta. Operated by Endeavor Air DBA Delta Connection · nonstop · 2h 12m
The catch: At Pod 51 you get a bunk pod with a shared bathroom, highs run 45–55°F, and a checked bag is about $140 for two.
Worth it if you'll spend your days out at museums and shows and only need a bunk to sleep in; skip it if you want a private bathroom.
All trips from Savannah · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. We use AI tools to draft the text of each page from the data on it; code checks every number in the draft against that data and rejects what does not match, and the team reviews pages and fixes or removes what readers report. How we pick · Report a mistake.
Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License