Chicago from Norfolk, Oct 16–18: $1,980 for two, all in
The verdict
Our verdict
Worth it, if
- 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
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.
Worth it if you don't mind a damp Friday: the trip is $1,980 for two. That's the flights at $1,060, plus the hotel at $794 and $126 in property fees, with taxes and fees included. It covers 2 nights, Oct 16–18, 2026, nonstop on United Express (operated by Republic Airways) in 2h 33m, and a checked bag and spending money are extra.
The total, before you go
$1,980 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $1,060 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights, two guests, taxes in | $794 |
| Resort fee, collected at the desk | $126 |
| The total, before you go | $1,980 |
| A checked bag each, round trip (not in the total) | about $160 |
$86 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
$530 per person, round trip
$1,060 for two, taxes and fees included · United. Operated by Republic Airways DBA United Express · nonstop · 2h 33m
Out Fri, Oct 16, 6:20 AM – Fri, Oct 16, 7:53 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| United. Operated by Republic Airways DBA United Express | $530 | nonstop | 2h 33m |
| United | $530 | nonstop | 2h 29m |
| American. Operated by Republic Airways as American Eagle | $530 | nonstop | 2h 51m |
Prices checked Oct 14, 2026, 10:03 PM 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
Tweak this trip
Why now
At $530 per person, the fare is $86 below the typical fare on this route, a 14% gap, based on 16 earlier checks. Across 12 offers we saw fares from $530 to $896 per person, and all three nonstops were $530 when we checked. The total is $1,980 for two, and that already counts the Loop hotel's $126 property fees. A checked bag, about $160 for two, isn't included. Mid-October in Chicago means highs of 57–63°F. Friday looks wet with a 78% chance of drizzle. Saturday turns overcast with a 13% chance, and Sunday looks clear at 1%, which makes it a good day for the lakefront. The early flight lands at 7:53 AM, so Friday still counts for architecture, museums, deep-dish and live blues.
The kind of trip this is
This is a city weekend for two: architecture from the river, a major art museum, deep-dish and a late night of blues. It suits couples or two friends who like to walk a lot and eat well. The pace is brisk because 2 nights go fast. Pack a jacket and an umbrella for Friday, then plan the outdoor sights for the drier days.
Weather in Chicago, Oct 16–18
Highs 57–63°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 59 °F | 48 °F | 78% |
| Sat, Oct 17 | 57 °F | 43 °F | 13% |
| Sun, Oct 18 | 63 °F | 48 °F | 1% |
Where to stay in Chicago
We picked Club Quarters Hotel Central Loop, Chicago as the best value. A Club Room is $794 for the stay ($397 a night), it's rated 8.2 from 5,335 reviews, and its $126 in property fees are already in our total. Central Loop Hotel is the budget pick at the same $794 ($397 a night) for a Double Room, rated 8.1 from 3,688 reviews, also with $126 in fees. Both are in The Loop, with architecture, theatres and Millennium Park at your doorstep. The top rated stay is Hotel Chicago Downtown, Autograph Collection in River North: 8.6 from 266 reviews at $1,130 ($565 a night), plus $180 in fees paid at the hotel. River North puts you near galleries, steakhouses and the city's nightlife core. None of the three offers free cancellation.
Club Quarters Hotel Central Loop, Chicago
$794 for 2 nights, two guests · $397 a night
See roomsHotel Chicago Downtown, Autograph Collection
$1,130 for 2 nights, two guests · $565 a night
See roomsCentral Loop Hotel
$794 for 2 nights, two guests · $397 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 Sunday, when the forecast is clear
- See the Bean and the fountains in Millennium Park, right by The Loop hotels
- Spend drizzly Friday inside the Art Institute of Chicago
- 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
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 Norfolk | Norfolk International (ORF) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 2h 33m nonstop |
| Distance | 697 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $1,060 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | $794 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,374 |
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 | $530 per person |
| Lowest in the last 30 days | $418 (Oct 15, 2026) |
| Typical price, last 60 days | $616 |
| Price checks | 16 |
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
- Chicago is 1 hour behind Norfolk, and the 697-mile nonstop takes 2h 33m
- You fly into Chicago O'Hare International (ORD); return flight times weren't in our check, so confirm them before you book
- All three hotels are room only, and none offers free cancellation
- Prices are all-in as we found them and can change before you book
Questions readers ask
Is it worth it?
Worth it if a wet Friday and a nonrefundable room don't bother you. The nonstop fare is $530 per person, 14% below the typical fare, and Saturday and Sunday look much drier, with highs up to 63°F.
How much is the whole trip for two?
$1,980 all in: $1,060 for flights, $794 for 2 nights at Club Quarters Hotel Central Loop, Chicago, and $126 in property fees. A checked bag, about $160 for two, plus meals and spending money are not included.
Do I need a passport?
No. It's a domestic trip from Norfolk, and you'll pay in US dollars.
What is the weather like?
The forecast for Friday is drizzle, a high of 59°F and a 78% chance of rain. Saturday is overcast at 57°F with a 13% chance, and Sunday is clear at 63°F with a 1% chance. Lows run 43–48°F.
Is 2 nights enough?
For a first look, yes. The 6:20 AM flight lands at 7:53 AM Friday, so you get most of Friday plus all of Saturday. We didn't have return times, so check how much of Sunday you keep.
Which flight should we take?
All three nonstops were $530 per person: United Express at 6:20 AM (2h 33m), United at 5:01 PM landing at 6:30 PM (2h 29m), and American Eagle at 6:29 PM landing at 8:20 PM (2h 51m).
Also found for you
The newest finds from Norfolk.
Just found · from NorfolkLowest in 30 daysWorth it, if
Destin & the Emerald Coast
Oct 30–Nov 1, 2026 · 2 nights
- Fare is $354 per person, $346 below the typical fare
- Village Inn Destin scores 8.1 from 1,144 reviews, with free cancellation
- Typical highs of 71–72°F, and Saturday, Oct 31 looks clear
$873 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $708 + hotel $148 + resort fee $17, taxes in · a checked bag each adds about $160
MX + G4 · with a stop · 18h 32m
The catch: With one stop, you land at 10:44 PM Friday and fly home at 6:45 AM Sunday, and a checked bag is about $160 for two.
Worth it if you can pack light and want one easy day by the Gulf; skip it if you want a slow, full weekend.
Tweak this trip
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.
Tweak this trip
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.
Tweak this trip
More trips
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
Destin & the Emerald Coast
Oct 30–Nov 1, 2026 · 2 nights
- Fare is $354 per person, $346 below the typical fare
- Village Inn Destin scores 8.1 from 1,144 reviews, with free cancellation
- Typical highs of 71–72°F, and Saturday, Oct 31 looks clear
$873 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights $708 + hotel $148 + resort fee $17, taxes in · a checked bag each adds about $160
MX + G4 · with a stop · 18h 32m
The catch: With one stop, you land at 10:44 PM Friday and fly home at 6:45 AM Sunday, and a checked bag is about $160 for two.
Worth it if you can pack light and want one easy day by the Gulf; skip it if you want a slow, full weekend.
All trips from Norfolk · 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.
Image credits
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License