Chicago from Norfolk, Oct 23–25: $1,559 for two, all in
The verdict
Our verdict
Worth it, if
- $108 per person below the typical fare on this route
- Highs 51–58°F, a small chance of rain
- No passport needed
The catch: Not nonstop: a stop on the way, 35h 58m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
Round trip from Norfolk to Chicago is $515 per person ($1,029 for two) for Oct 23–25, 2026, 2 nights, on F9 with 1 stop each way, so it's not nonstop. The forecast shows highs of 51–58°F with a small chance of rain, and the best-value hotel, Hilton Chicago, is $530 for the stay.
The total, before you go
$1,559 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $1,029 |
| Hilton Chicago, 2 nights, two guests, taxes in | $530 |
| The total, before you go | $1,559 |
| A checked bag each, round trip (not in the total) | about $240 |
$108 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $60 each way per bag on Frontier, $240 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
$515 per person, round trip
$1,029 for two, taxes and fees included · Frontier · 1 stop · 35h 58m
Out Fri, Oct 23, 3:48 PM – Sat, Oct 24, 7:51 AM · back Sun, Oct 25, 6:58 PM – Mon, Oct 26, 2:53 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $515 | 1 stop | 35h 58m |
| MX + F9 | $655 | 1 stop | 32h 57m |
| Frontier | $537 | 2 stops | 35h 12m |
Prices checked Oct 14, 2026, 3:10 AM EDT. Prices change; the binding price is the one on the booking site.
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Why now
At $515 per person, this fare is $108 below the typical fare on this route ($623), or 17% under. We saw 12 offers between $515 and $716, and this one is at the bottom of that range. It's not the low for the month, though: the fare dropped to $418 on Oct 12. Prices are all-in, taxes and fees included, as of when we checked, and they can change. Here's the catch. You leave Norfolk Friday, Oct 23 at 3:48 PM and land at O'Hare Saturday, Oct 24 at 7:51 AM. The flight home leaves Sunday at 6:58 PM and gets in Monday, Oct 26 at 2:53 PM. Late October means highs of 51–58°F, which is jacket weather for walking the Loop, ducking into museums and ending the night with deep-dish.
The kind of trip this is
This is a city getaway built around food, architecture and culture: skyscrapers from the river, a world-class art museum, deep-dish pizza and a late blues set. It suits a couple or two friends who like to walk a lot and plan a little. The pace is tight, since you arrive Saturday morning and fly out Sunday evening, so you get one full day plus most of the next.
Weather in Chicago, Oct 23–25
Highs 51–58°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 51 °F | 47 °F | 30% |
| Sat, Oct 24 | 58 °F | 47 °F | 22% |
| Sun, Oct 25 | 54 °F | 42 °F | 17% |
Where to stay in Chicago
Hilton Chicago is the best-value pick at $530 for the 2 nights ($265 a night) for a Double Room, with a 7.9 review score from 983 reviews. It's room only and has no free cancellation. Hampton Inn Chicago West Loop Fulton Market Area is the top rated at 8.8 from 774 reviews. It costs $628 for the stay ($314 a night), includes breakfast and has no free cancellation. It puts you in the West Loop, where converted warehouses line the restaurant row on Randolph Street. Congress Plaza Hotel Chicago is our budget pick, at $588 ($294 a night) for a King Room with a 7.1 score from 4,534 reviews. It's the only one of the three with free cancellation. Both the Hilton and the Congress Plaza are in The Loop, so architecture, theatres and Millennium Park are right outside.
Hilton Chicago
$530 for 2 nights, two guests · $265 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
$628 for 2 nights, two guests · $314 a night
See roomsCongress Plaza Hotel Chicago
$588 for 2 nights, two guests · $294 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 to see the skyline from the water
- See the Bean and the fountains in Millennium Park, steps from the Loop hotels
- Spend a few hours at the Art Institute of Chicago, good for the drizzly Sunday
- Eat deep-dish at Lou Malnati's or Pequod's and compare notes
- Hear live blues at Kingston Mines on Saturday night
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 Norfolk | Norfolk International (ORF) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 35h 58m (1 stop) |
| Distance | 697 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $1,030 |
| Hotel, 2 nights (Hilton Chicago) | $530 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,080 |
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: Norfolk to Chicago
| Per person | |
|---|---|
| This trip | $515 per person |
| Lowest in the last 30 days | $418 (Oct 12, 2026) |
| Typical price, last 60 days | $623 |
| 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).
- No passport needed, and you pay in US dollars.
- Chicago is 1 hour behind Norfolk.
- The trip is 697 miles each way, but the 1-stop itinerary adds up to 35h 58m of travel across both legs.
- You land Saturday morning, so the Friday hotel night mostly covers time you spend traveling.
- Our rough budget for two is $2,080: $1,030 for flights, $530 for the Hilton and $520 for spending, or $130 per person a day.
Questions readers ask
How much is the flight?
$515 per person round trip, or $1,029 for two, all-in as of when we checked. That's $108 below the typical fare on this route. The fare can change before you book.
When do I actually get there and back?
You leave Norfolk Friday, Oct 23 at 3:48 PM and land at O'Hare Saturday, Oct 24 at 7:51 AM. The return leaves Sunday, Oct 25 at 6:58 PM and lands Monday, Oct 26 at 2:53 PM, so plan around Monday.
Do I need a passport?
No. It's a domestic trip, you pay in US dollars, and Chicago is 1 hour behind Norfolk.
What is the weather like?
The forecast shows Friday clear at 51°F, Saturday overcast at 58°F with a 22% chance of rain, and Sunday drizzle at 54°F with a low of 42°F. Bring a warm layer and a rain jacket.
Is 2 nights enough?
You really get Saturday and most of Sunday. That's enough for the river cruise, Millennium Park, the Art Institute, deep-dish and a blues night, as long as you stay central in The Loop.
Which hotel should we pick?
Hilton Chicago at $530 for the stay if price matters most. Hampton Inn Chicago West Loop Fulton Market Area at $628 if you want breakfast and the 8.8 score. Congress Plaza Hotel Chicago at $588 if you need free cancellation.
Also found for you
The newest finds from Norfolk.
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Bar Harbor & Acadia
Oct 23–25, 2026 · 2 nights
- $494 per person, $108 below the typical fare on this route
- Atlantic Eyrie Lodge: 8.5 from 1,325 reviews, breakfast, free cancellation
- Overcast weekend, highs 48–57°F, rain chance only 12% to 18%
$1,530 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $988 + hotel $501 + resort fee $41, taxes in · a checked bag each adds about $240
F9 + G4 · with a stop · 37h 43m
The catch: One stop and 37h 43m out means you land Saturday at 10:08 AM, and a checked bag is about $240 for two.
Worth it if you want one last fall weekend in Acadia and can take Monday off; skip it if a 37h 43m trip up feels like too much.
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Just found · from NorfolkLowest in 30 daysWorth it, if
New York City
Nov 19–23, 2026 · 4 nights
- $377 per person, $326 below the typical fare on this route
- Times Square hotel rated 8.4 from 4,624 reviews, free cancellation
- Four nights for Broadway, the Met and the Brooklyn Bridge
$1,742 for two · 4 nights · flights, hotel, taxes & fees
Flights $753 + hotel $989, taxes in · a checked bag each adds about $240
Frontier · with a stop · 17h 6m
The catch: The cheapest fare has two stops and 1,026 minutes of travel for a 297-mile trip, and resort fees and a checked bag are not in the total.
Worth it if you'd trade a long travel day for a $1,742 city getaway; skip it if you need a quick, simple flight.
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Just found · from NorfolkWorth it, if
Key West
Nov 27–Dec 1, 2026 · 4 nights
- $118 per person below the highest fare we saw for these dates
- Blue Flamingo Resort Key West, rated 8.4 by 1,583 guests
- Typical highs 75–77°F, lows near 73°F this time of year
$1,782 for two · 4 nights · flights, hotel, taxes & fees
Flights $665 + hotel $1,117, taxes in · a checked bag each adds about $240
F9 + G4 · with a stop · 22h 30m
The catch: Not nonstop: 2 stops on the way, 22h 30m 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 NorfolkWorth it, if
Chicago
Oct 16–18, 2026 · 2 nights
- Nonstop on United, 2h 33m, leaving at 6:20 AM Friday
- $530 per person, $86 below the typical fare on this route
- Club Quarters in The Loop, rated 8.2 from 5,335 reviews
$1,980 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $1,060 + hotel $794 + resort fee $126, taxes in · a checked bag each adds about $160
United. Operated by Republic Airways DBA United Express · nonstop · 2h 33m
The catch: Friday has a 78% chance of drizzle, none of the three hotels offers free cancellation, and a checked bag is about $160 for two, which isn't in the total.
Worth it if you want a walkable city weekend of museums, food and blues; skip it if you need a refundable room or can't stand drizzle.
The weekend after · from Norfolk27% below typical
Orlando
Oct 23–25, 2026 · 2 nights
- Frontier nonstop, 2h 12m, leaves Norfolk 3:48 PM Friday
- $289 per person, $108 below the typical fare on this route
- Westgate Town Center Resort: 8.5 from 1,757 reviews, free cancellation
$882 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $578 + hotel $272 + resort fee $32, taxes in · a checked bag each adds about $240
Frontier · nonstop · 2h 12m
The catch: A checked bag is about $240 for two on top of the $882 total, so pack light or budget for it.
Worth it if you want a quick, warm theme-park weekend for two; skip it if you need checked bags or want more than 2 nights.
A week away · from NorfolkWorth it, if
Sedona
Nov 14–21, 2026 · 7 nights
- Cowboy Hideout one-bedroom apartment, rated 9.6, with free cancellation
- Typical highs of 55–66°F, mild weather for red-rock hiking
- $369 per person on American, departs 7:19 AM, lands 12:55 PM
$1,757 for two · 7 nights · flights, hotel, taxes, fees & the resort fee
Flights $738 + hotel $904 + resort fee $115, taxes in · a checked bag each adds about $160
American. Operated by PSA Airlines as American Eagle · with a stop · 7h 36m
The catch: It's one stop and 7h 36m to Phoenix, then Sedona is two hours north, and checked bags are about $160 for two, not in the total.
Worth it if you want a week of hiking in mild weather and don't mind a connection; skip it if you only fly nonstop.
Just found · from NorfolkLowest in 30 daysWorth it, if
Bar Harbor & Acadia
Oct 23–25, 2026 · 2 nights
- $494 per person, $108 below the typical fare on this route
- Atlantic Eyrie Lodge: 8.5 from 1,325 reviews, breakfast, free cancellation
- Overcast weekend, highs 48–57°F, rain chance only 12% to 18%
$1,530 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $988 + hotel $501 + resort fee $41, taxes in · a checked bag each adds about $240
F9 + G4 · with a stop · 37h 43m
The catch: One stop and 37h 43m out means you land Saturday at 10:08 AM, and a checked bag is about $240 for two.
Worth it if you want one last fall weekend in Acadia and can take Monday off; skip it if a 37h 43m trip up feels like too much.
All trips from Norfolk · Chicago from every city · Prices on this route · Trips in October 2026 · Home
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Image credits
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