Chicago from Savannah, Oct 16–18: round trip from $553
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 flight
$690 $553 per person, round trip
the typical fare on this route
$1,106 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 | $553 | 1 stop | 5h 15m |
| United. Operated by Republic Airways DBA United Express | $579 | nonstop | 2h 39m |
| American | $553 | 1 stop | 4h 28m |
Prices checked Oct 12, 2026, 2:48 PM 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 | $1,106 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights | $490 |
| Trip total for two | $1,596 |
Regular: $1,870 You pay: $1,596 Saved: $274
the typical fare on this route.
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Why go 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, Oct 16–18
Highs 53–62°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 57 °F | 46 °F | 51% |
| Sat, Oct 17 | 53 °F | 45 °F | 2% |
| Sun, Oct 18 | 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
$490 for 2 nights, two guests · $245 a night
See roomsCanopy By Hilton Chicago Central Loop
$962 for 2 nights, two guests · $481 a night
See roomsCongress Plaza Hotel Chicago
$750 for 2 nights, two guests · $375 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 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
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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 | 5h 15m (1 stop) |
| Distance | 767 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $1,106 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | $490 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,116 |
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 | $553 per person |
| Lowest in the last 30 days | $553 (Oct 12, 2026) |
| Typical price, last 60 days | $690 |
| Price checks | 5 |
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 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.
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Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License