Chicago from Nashville, Oct 23–25: $1,310 for two, all in
The verdict
Our verdict
Worth it, if
- $31 per person below the typical fare on this route
- Highs 58–70°F, little rain expected
- No passport needed
The catch: Not nonstop: a stop on the way, 33h 20m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Round-trip flights from Nashville to Chicago cost $309 per person ($618 for two) for Oct 23–25, 2026, 2 nights, on Contour Airlines with 1 stop, so not nonstop. The forecast shows highs of 58–72°F and a small chance of rain. Hilton Chicago is the best-value hotel at $522 for both nights, but heads-up: the cheapest outbound we found doesn't land until Saturday at 5:20 PM.
The total, before you go
$1,310 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $622 |
| Hilton Chicago, 2 nights, two guests, taxes in | $594 |
| Resort fee, collected at the desk | $94 |
| The total, before you go | $1,310 |
| A checked bag each, round trip (not in the total) | about $160 |
$31 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, $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
$311 per person, round trip
$622 for two, taxes and fees included · Contour Airlines. Operated by Contour Airlines as Public Charter + Contour Airlines as Public Charter · 1 stop · 33h 20m
Out Fri, Oct 23, 8:00 AM – Sat, Oct 24, 5:20 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Contour Airlines. Operated by Contour Airlines as Public Charter + Contour Airlines as Public Charter | $311 | 1 stop | 33h 20m |
| LF | $337 | 1 stop | 11h 29m |
| LF | $343 | 1 stop | 18h 47m |
Prices checked Oct 15, 2026, 1:15 AM CDT. Prices change; the binding price is the one on the booking site.
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Why now
At $309 per person round trip, this fare is $34 below the typical fare on this route, or 10% under. It also carries the Lowest in 30 days badge. Across 12 offers we checked, fares ran from $309 to $400. The forecast: 72°F with rain on Friday, 65°F and clear on Saturday, 58°F and overcast on Sunday. That's good weather for museums and dinners out: the Art Institute, a river cruise, deep-dish. Now the catch. The $309 fare leaves Friday at 8:00 AM and lands Saturday at 5:20 PM, which is 33h 20m with 1 stop for a 398-mile trip. You'd lose most of the weekend and pay for a hotel night you don't use. If you want Friday in the city, we also found a $343 fare that lands Friday at 11:40 AM. All prices include taxes and fees as found and can change.
The kind of trip this is
This is a city weekend built around food, culture and nightlife: architecture from the river, a world-class art museum, deep-dish pizza and late blues sets. It suits couples or a pair of friends who like to walk, eat well and stay out a little late. Expect an easy pace with a couple of big sights a day and long dinners in between. Late October weather means a jacket, not a beach towel.
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 | 17% |
Where to stay in Chicago
Hilton Chicago is our best-value pick: $522 for the 2 nights ($261 a night) for a Double Room, room only, with a review score of 7.9 from 983 reviews, in the Chicago Loop. Hampton Inn Chicago McCormick Place is the top rated of the three at 8.5 from 734 reviews. It's $546 total ($273 a night), includes breakfast and sits in the South Loop. Congress Plaza Hotel Chicago is the 4-star option and the only one of the three with free cancellation. It's $588 total ($294 a night) for a King Room, rated 7.1 from 4,532 reviews. The Loop puts architecture, theatres and Millennium Park at your doorstep. If nightlife and steakhouses matter more, look at River North.
Hilton Chicago
$594 for 2 nights, two guests · $297 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
$630 for 2 nights, two guests · $315 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
- Take the Chicago Architecture Foundation river cruise for the skyline from the water.
- See the Bean and the fountains in Millennium Park, steps from The Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's, or try both and settle the debate.
- Spend a rainy afternoon inside the Art Institute of Chicago.
- Hear live blues at Kingston Mines once the sun goes down.
- Walk Randolph Street in the West Loop for its restaurant row.
Also worth it
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
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Getting there and around
| Airports in Nashville | Nashville International (BNA) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 33h 20m (1 stop) |
| Distance | 398 miles each way |
| Time difference | same time zone |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $622 |
| Hotel, 2 nights (Hilton Chicago) | $594 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,736 |
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: Nashville to Chicago
| Per person | |
|---|---|
| This trip | $311 per person |
| Lowest in the last 30 days | $272 (Oct 15, 2026) |
| Typical price, last 60 days | $342 |
| Price checks | 14 |
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).
- No passport needed. It's a domestic trip, paid in US dollars, with no time difference from Nashville.
- The $309 fare has 1 stop and takes 33h 20m: it departs Friday, Oct 23 at 8:00 AM and arrives Saturday, Oct 24 at 5:20 PM at O'Hare (ORD).
- Only Congress Plaza Hotel Chicago offers free cancellation. Hilton Chicago and Hampton Inn Chicago McCormick Place don't.
- Our rough budget for two is $1,660: $618 for flights, $522 for the hotel and $520 for spending.
- Prices include taxes and fees as found when we checked. They can change before you book on the airline's or hotel's site.
Questions readers ask
How much is the flight?
$309 per person round trip, or $618 for two, on Contour Airlines with 1 stop. That's $34 below the typical fare on this route. The price includes taxes and fees as found when we checked.
When would I actually get to Chicago?
The $309 fare leaves Nashville on Friday, Oct 23 at 8:00 AM and lands at O'Hare on Saturday, Oct 24 at 5:20 PM, 33h 20m in total. We also found a $343 fare that lands Friday at 11:40 AM.
Is 2 nights enough?
With the $343 fare that lands Friday at 11:40 AM, 2 nights covers a river cruise, the Art Institute, Millennium Park and a night of blues. With the $309 fare you arrive Saturday at 5:20 PM, so you'd get one evening plus whatever time you have Sunday.
What is the weather like?
Friday is 72°F with rain and a 34% chance of showers. Saturday is clear at 65°F, and Sunday is overcast at 58°F with lows near 53°F. Bring a layer and an umbrella.
Do I need a passport?
No. Chicago is a domestic trip from Nashville, you'll pay in US dollars, and both cities are on the same clock.
What does the whole weekend cost for two?
Our estimate is $1,660 for two: $618 in flights, $522 for 2 nights at Hilton Chicago and $520 for spending money.
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All trips from Nashville · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
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Image credits
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