Chicago from Cleveland, 16 – 18 Oct: £1,238 for two, all in
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The verdict
Our verdict
Worth it, if
- £167 per person below the typical fare on this route
- Lowest in 30 days on this route
- Hyatt Place Chicago/Downtown - The Loop, rated 8.2 by 1,959 guests
The catch: Not nonstop: a stop on the way, 12h 31m in all.
Worth it if you want to walk, eat and see things; skip it if you want to switch off.
When we checked, round-trip flights from Cleveland to Chicago were $394 per person ($788 for two) for Oct 16–18, 2026, a 2-night weekend. The fare is on Frontier with 1 stop, so it isn't nonstop. Friday looks drizzly at 58°F and Sunday clears to 65°F, and the best-value hotel is $854 for the stay.
The total, before you go
£1,238 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £594 |
| Hyatt Place Chicago/Downtown - The Loop, 2 nights, two guests, taxes in | £644 |
| The total, before you go | £1,238 |
| Hold luggage each, return (not in the total) | about £181 |
£167 per person below the typical fare on this route.
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
£297 per person, return
£594 for two, taxes and fees included · Frontier · 1 stop · 12h 31m
Out Fri, Oct 16, 7:00 AM – Fri, Oct 16, 6:31 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £297 | 1 stop | 12h 31m |
| American. Operated by Republic Airways as American Eagle | £432 | nonstop | 1h 37m |
| JetBlue | £418 | 1 stop | 6h 24m |
Prices checked 14 Oct 2026, 01:38 GMT-4. Prices change; the binding price is the one on the booking site.
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Why now
At $394 per person round trip, this fare is $221 below the typical fare on this route, which is $615 per person. That's 36% under, and it's the lowest fare in our last 30 days of checks on this route. Flights for two come to $788. Add the best-value hotel and $130 per person per day for spending, and our rough budget for two is $2,162. Mid-October in Chicago means museums and food more than beaches. Highs are 58°F on Friday and Saturday, and Sunday is clear at 65°F. It's a good fit for the Art Institute, a river cruise and a deep-dish dinner. One heads-up: the low fare has 1 stop and takes 12h 31m on the way out, for a 307-mile trip. The nonstop American flight we found was $573 per person and takes 1h 37m.
The kind of trip this is
This is a city weekend built around food and culture. You've got architecture from the river, a top art museum, deep-dish pizza and live blues late at night. It suits couples or a pair of friends who like walking a city and eating well. The pace is easy, with one or two big sights a day and an evening out. Bring a jacket, since the weather runs cool and Friday looks wet.
Weather in Chicago, 16 – 18 Oct
Highs 58–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 58 °F | 48 °F | 78% |
| Sat 17 Oct | 58 °F | 45 °F | 7% |
| Sun 18 Oct | 65 °F | 49 °F | 0% |
Where to stay in Chicago
For value, go with Hyatt Place Chicago/Downtown - The Loop: $854 for the 2 nights ($427 a night), a review score of 8.2 from 1,959 reviews and free cancellation. If you want the top-rated pick, Hyatt Regency McCormick Place Chicago in the South Loop is $1,020 for the stay ($510 a night) and scores 8.5 from 1,003 reviews, but it can't be cancelled for free. Club Quarters Hotel Central Loop, Chicago is our budget pick, a 4-star at $893 for the stay ($447 a night) with a score of 8.2 from 5,339 reviews. It also doesn't offer free cancellation. Two of the three are in The Loop, which puts the architecture, the theaters and Millennium Park right outside your door. All three are room only.
Hyatt Place Chicago/Downtown - The Loop
£644 for 2 nights, two guests · £322 a night
See roomsHyatt Regency McCormick Place Chicago
£769 for 2 nights, two guests · £384 a night
See roomsClub Quarters Hotel Central Loop, Chicago
£673 for 2 nights, two guests · £337 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, a short walk from The Loop hotels.
- Eat deep-dish at Lou Malnati's or Pequod's.
- Spend Friday's drizzly afternoon inside the Art Institute of Chicago.
- Hear live blues at Kingston Mines on Saturday night.
- Head to West Loop for the restaurant row on Randolph Street.
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 Cleveland | Cleveland Hopkins International (CLE) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 12h 31m (1 stop) |
| Distance | 307 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £594 |
| Hotel, 2 nights (Hyatt Place Chicago/Downtown - The Loop) | £644 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,630 |
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: Cleveland to Chicago
| Per person | |
|---|---|
| This trip | £297 per person |
| Lowest in the last 30 days | £297 (14 Oct 2026) |
| Typical price, last 60 days | £464 |
| Price checks | 7 |
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).
- You don't need a passport, and you'll pay in US dollars.
- Chicago is 1 hour behind Cleveland. The outbound flight leaves CLE at 7:00 AM and lands at ORD at 6:31 PM local time.
- The $394 fare has 1 stop and takes 12h 31m. Chicago is 307 miles away, so expect most of Friday to go to travel.
- Only Hyatt Place Chicago/Downtown - The Loop has free cancellation. All three hotels are room only.
- Prices include taxes and fees as we found them. They can change before you book.
Questions readers ask
How much is the flight?
When we checked, it was $394 per person round trip on Frontier, or $788 for two, taxes and fees included. That's $221 below the typical fare on this route. Prices can change before you book.
Is there a nonstop option?
Yes. American, operated by Republic Airways as American Eagle, had a nonstop for $573 per person. It leaves at 5:12 AM and takes 1h 37m. The $394 Frontier fare has 1 stop and takes 12h 31m.
Do I need a passport?
No. It's a domestic trip from Cleveland Hopkins International to Chicago O'Hare International, and you'll pay in US dollars. Chicago is 1 hour behind Cleveland.
What is the weather like?
The forecast shows drizzle on Friday, Oct 16, with a 78% chance of rain and a high of 58°F. Saturday looks overcast at 58°F with a 7% chance of rain. Sunday is clear at 65°F.
Is 2 nights enough?
It's enough for a river cruise, Millennium Park, the Art Institute, deep-dish and a blues night. With the 1-stop fare, though, you'll land at 6:31 PM on Friday, so your real sightseeing time is Saturday and Sunday.
What does the whole weekend cost for two?
Our rough budget is $2,162 for two. That's $788 for flights, $854 for Hyatt Place Chicago/Downtown - The Loop and $520 for spending, which works out to $130 per person per day.
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All trips from Cleveland · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License