Chicago from Cleveland, Oct 16–18: $1,642 for two, all in
The verdict
Our verdict
Worth it, if
- $394 per person, $221 below the typical fare on this route
- Hyatt Place in The Loop scores 8.2 from 1,959 reviews
- Free cancellation at Hyatt Place, and Sunday looks clear at 65°F
The catch: The Frontier fare has one stop and takes 12h 31m on the way out for a 307-mile trip, and a checked bag is about $240 for two.
Worth it if a full travel day Friday is fine for this price; skip it if you'd rather pay $573 per person for the 1h 37m nonstop.
Worth it if you can spend Friday getting there. The trip costs $1,642 for two: the flights at $788 plus the Hyatt Place Chicago/Downtown - The Loop at $854, with taxes and fees included but not checked bags or spending money. You go Oct 16–18, 2026 for 2 nights on Frontier, which isn't nonstop: one stop and 12h 31m on the way out, leaving at 7:00 AM and landing at 6:31 PM.
The total, before you go
$1,642 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, round trip | $788 |
| Hyatt Place Chicago/Downtown - The Loop, 2 nights, two guests, taxes in | $854 |
| The total, before you go | $1,642 |
| A checked bag each, round trip (not in the total) | about $240 |
$221 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
$394 per person, round trip
$788 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 | $394 | 1 stop | 12h 31m |
| American. Operated by Republic Airways as American Eagle | $573 | nonstop | 1h 37m |
| JetBlue | $555 | 1 stop | 6h 24m |
Prices checked Oct 14, 2026, 1:38 AM EDT. Prices change; the binding price is the one on the booking site.
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Tweak this trip
Why now
At $394 per person, the fare is $221 below the typical fare on this route, or 36% under it, and it has the Lowest in 30 days badge from our checks. With the Hyatt Place, that puts the whole weekend at $1,642 for two, taxes and fees included. Checked bags and spending money are extra. Mid-October in Chicago looks like jacket weather. Friday, Oct 16 has a 78% chance of drizzle and a high of 58°F. Saturday is overcast at 58°F with a 7% chance of rain, and Sunday clears to 65°F. That suits a weekend of museums and food, with the river cruise saved for the clear Sunday. These prices were found when we checked and can change.
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 downtown, eat well and go out at night. The pace is short and full: Friday is mostly travel, Saturday is for the Art Institute and deep-dish, and Sunday is for the river and Millennium Park before you head home.
Weather in Chicago, Oct 16–18
Highs 58–65°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 58 °F | 48 °F | 78% |
| Sat, Oct 17 | 58 °F | 45 °F | 7% |
| Sun, Oct 18 | 65 °F | 49 °F | 0% |
Where to stay in Chicago
We priced three hotels for the 2 nights. Hyatt Place Chicago/Downtown - The Loop is the best value and the one in the total. It's $854 for the stay ($427 a night) and scores 8.2 from 1,959 reviews, with a King Room with Sofa Bed and free cancellation. Club Quarters Hotel Central Loop, Chicago is also in the Loop. It's $893 ($447 a night) and has the same 8.2 score from 5,339 reviews, but no free cancellation. Hyatt Regency McCormick Place Chicago in the South Loop is the top rated, at 8.5 from 1,003 reviews. It costs $1,020 ($510 a night), also without free cancellation. The Loop puts architecture, theatres and Millennium Park at your doorstep, which helps on a short weekend.
Hyatt Place Chicago/Downtown - The Loop
$854 for 2 nights, two guests · $427 a night
See roomsHyatt Regency McCormick Place Chicago
$1,020 for 2 nights, two guests · $510 a night
See roomsClub Quarters Hotel Central Loop, Chicago
$893 for 2 nights, two guests · $447 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 Sunday, the clear day at 65°F
- See the Bean and the fountains in Millennium Park
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend drizzly Friday evening or Saturday at the Art Institute of Chicago
- Hear live blues at Kingston Mines
- Catch a Cubs game at Wrigley Field if one is on that weekend
Also worth it
- Visit the Art Institute of Chicago
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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 | $788 |
| Hotel, 2 nights (Hyatt Place Chicago/Downtown - The Loop) | $854 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,162 |
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 | $394 per person |
| Lowest in the last 30 days | $394 (Oct 14, 2026) |
| Typical price, last 60 days | $615 |
| Price checks | 7 |
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 Cleveland.
- The Frontier fare flies from Cleveland Hopkins International (CLE) to Chicago O'Hare International (ORD).
- A checked bag is about $240 for two and isn't in the $1,642 total.
- Our budget adds $520 of spending money for two, which brings the trip to $2,162.
Questions readers ask
Is it worth it?
Worth it if you don't mind losing Friday to travel. The fare is $394 per person, 36% under the typical fare on this route. The outbound has one stop and takes 12h 31m.
How much is the whole trip for two?
It's $1,642 for two, taxes and fees included: $788 for the flights and $854 for 2 nights at Hyatt Place Chicago/Downtown - The Loop. Checked bags (about $240 for two) and spending money aren't included.
Is there a nonstop?
Yes. When we checked, American had a nonstop of 1h 37m, operated by Republic Airways as American Eagle, at $573 per person, or $1,146 for two.
What is the weather like?
Friday, Oct 16 has a 78% chance of drizzle and a high of 58°F. Saturday is overcast at 58°F with a 7% chance of rain. Sunday is clear at 65°F.
Is 2 nights enough?
For the highlights, yes, but with a 6:31 PM arrival on Friday, Saturday and Sunday are your real sightseeing days. Plan on the Art Institute, deep-dish, Millennium Park and the river cruise.
Do I need a passport?
No. It's a domestic trip, you pay in US dollars, and Chicago is 1 hour behind Cleveland.
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