Chicago from Washington, DC, 16 – 18 Oct: £899 for two, all in
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The verdict
Our verdict
Worth it, if
- $354 per person, $12 under the typical $366 on this route
- Saturday mostly clear at 52°F, Sunday clear at 61°F
- Sleep Inn Midway Airport: $369 for 2 nights, breakfast, free cancellation
The catch: The Frontier flight has one stop and takes 7h 24m, landing at 12:24 AM Saturday; a checked bag is about $240 for two and isn't in the total.
Worth it if you want a low-cost city weekend and don't mind a late arrival; skip it if you need a nonstop or a downtown hotel.
Worth it if a late Friday arrival doesn't bother you. The whole trip is $1,193 for two: Frontier flights at $708 plus 2 nights at the Holiday Inn Chicago Midway Airport S by IHG at $485, taxes and fees included, for Oct 16–18, 2026. The Frontier flight is not nonstop: it has one stop out of DCA and lands at O'Hare.
The total, before you go
£899 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £534 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights, two guests, taxes in | £366 |
| The total, before you go | £899 |
| Hold luggage each, return (not in the total) | about £181 |
Not in it: seat selection on basic fares and hold luggage (about £45 each way per bag on Frontier, £181 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
£267 per person, return
£534 for two, taxes and fees included · Frontier · 1 stop · 7h 24m
Out Fri, Oct 16, 6:00 PM – Sat, Oct 17, 12:24 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £267 | 1 stop | 7h 24m |
| United | £372 | nonstop | 2h 15m |
| American | £372 | nonstop | 2h 26m |
Prices checked 12 Oct 2026, 04:01 GMT-4. Prices change; the binding price is the one on the booking site.
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Why now
At $354 per person, the Frontier fare is $12 below the $366 median of our earlier checks on this route, about 3% less, and it's the lowest in 30 days. With the Holiday Inn near Midway, that comes to $1,193 for two, all in. Checked bags and spending money aren't in that number; we'd plan on about $520 for two for food and getting around. The forecast is good for a city weekend: a 33% chance of drizzle on Friday, then a mostly clear Saturday at 52°F and a clear Sunday at 61°F. That's good weather for a river cruise and a walk through Millennium Park. Pack a jacket for lows of 44–45°F. If you'd rather leave in the morning, a United or American nonstop is $493 per person.
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 a lot, eat well and stay out late. The pace is full but easy: one big museum, one river cruise, deep-dish pizza and a blues club. Cool fall weather makes it a jacket-and-sneakers trip, not a beach one.
Weather in Chicago, 16 – 18 Oct
Highs 52–61°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 60 °F | 45 °F | 33% |
| Sat 17 Oct | 52 °F | 44 °F | 4% |
| Sun 18 Oct | 61 °F | 45 °F | 6% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best value and the hotel in our total: $485 for 2 nights ($243 a night), rated 7.5 from 226 reviews. It's room only and has no free cancellation. Sleep Inn Midway Airport is the budget pick at $369 for the stay ($185 a night), rated 7.3 from 726 reviews, with breakfast and free cancellation. Both are near Midway, not downtown. Hyatt Regency McCormick Place Chicago is the top rated, at 8.5 from 998 reviews. It costs $1,020 for the stay ($510 a night), has free cancellation and sits in the South Loop, closer to the center. If you'd rather stay downtown, The Loop puts Millennium Park and the theatres at your door, and River North is the city's nightlife core.
Holiday Inn Chicago Midway Airport S by IHG
£366 for 2 nights, two guests · £183 a night
See roomsHyatt Regency McCormick Place Chicago
£769 for 2 nights, two guests · £384 a night
See roomsSleep Inn Midway Airport
£278 for 2 nights, two guests · £139 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 clear Saturday
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend a morning at the Art Institute of Chicago
- 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 Washington, DC | Ronald Reagan Washington National (DCA), Washington Dulles International (IAD), Baltimore/Washington International Thurgood Marshall (BWI) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 7h 24m (1 stop) |
| Distance | 593 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £534 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | £366 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,291 |
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: Washington, DC to Chicago
| Per person | |
|---|---|
| This trip | £267 per person |
| Lowest in the last 30 days | £267 (12 Oct 2026) |
| Typical price, last 60 days | £276 |
| Price checks | 8 |
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, and you'll pay in US dollars
- Chicago is 1 hour behind Washington, DC
- The Frontier flight leaves DCA at 6:00 PM Friday and lands at O'Hare at 12:24 AM
- The Holiday Inn rate is room only and has no free cancellation
- Prices are all-in as found when we checked; they can change
Questions readers ask
Is it worth it?
Worth it if you're fine with one stop and a 12:24 AM arrival. The fare is $354 per person, the lowest in 30 days, and the weekend forecast is mostly dry, with highs of 52–61°F.
How much is the whole trip for two?
$1,193 for two, all in: $708 for the Frontier flights plus $485 for 2 nights at the Holiday Inn Chicago Midway Airport S by IHG. A checked bag, about $240 for two, and spending money are extra.
Is there a nonstop?
Yes. United and American both fly nonstop on Friday morning for $493 per person, $986 for two. The United flight takes 2h 15m, against 7h 24m for the Frontier flight with one stop.
What is the weather like?
Friday has a high of 60°F and a 33% chance of drizzle. Saturday is mostly clear at 52°F, and Sunday is clear at 61°F, with lows around 44–45°F.
Is 2 nights enough?
For a first look, yes. Since you land late Friday, Saturday and Sunday are your two full days: enough for the river cruise, Millennium Park, the Art Institute and a deep-dish dinner.
Do I need a passport?
No. It's a domestic trip of 593 miles, you pay in US dollars and Chicago is 1 hour behind DC.
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
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