$39 Cheap flight deals from Detroit (DTT) to Chicago (CHI)

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This Weekend's Flight Deals from Detroit to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, May 4 - Tue, May 20
DTW
Detroit Metropolitan Wayne County
MDW
Midway Intl.
$188 Roundtrip, found 3 days ago
$188
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, May 4 from Detroit Metropolitan Wayne County to Midway Intl., returning Tue, May 20, priced at $188 found 3 days ago
Fri, May 2 - Sat, May 17
FNT
Bishop Intl.
ORD
O'Hare Intl.
$259 Roundtrip, found 2 days ago
$259
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, May 2 from Bishop Intl. to O'Hare Intl., returning Sat, May 17, priced at $259 found 2 days ago
Sun, May 4 - Mon, May 5
DTW
Detroit Metropolitan Wayne County
ORD
O'Hare Intl.
$290 Roundtrip, found 1 hour ago
$290
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, May 4 from Detroit Metropolitan Wayne County to O'Hare Intl., returning Mon, May 5, priced at $290 found 1 hour ago

Airfares from $39 One Way, $77 Round Trip from Detroit to Chicago

Prices starting at $77 for return flights and $39 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Jul 9 - Wed, Jul 16
DTW
Detroit
MDW
Chicago
$77 Roundtrip, found 1 day ago
$77
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Jul 9 from Detroit to Chicago, returning Wed, Jul 16, priced at $77 found 1 day ago
Wed, May 28 - Thu, May 29
DTW
Detroit
ORD
Chicago
$77 Roundtrip, just found
$77
Roundtrip
just found
Select United flight, departing Wed, May 28 from Detroit to Chicago, returning Thu, May 29, priced at $77 just found
Tue, Sep 16 - Wed, Sep 17
DTW
Detroit
MDW
Chicago
$77 Roundtrip, found 1 day ago
$77
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 16 from Detroit to Chicago, returning Wed, Sep 17, priced at $77 found 1 day ago
Thu, Jun 19 - Mon, Jun 23
DTW
Detroit
ORD
Chicago
$78 Roundtrip, found 2 days ago
$78
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Jun 19 from Detroit to Chicago, returning Mon, Jun 23, priced at $78 found 2 days ago
Tue, Jul 22 - Mon, Jul 28
DTW
Detroit
ORD
Chicago
$84 Roundtrip, found 1 day ago
$84
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jul 22 from Detroit to Chicago, returning Mon, Jul 28, priced at $84 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

8.8/10 Excellent! (1,610 reviews)

Jun 5 - Jun 7

2 night stay

Detroit (DTW) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Detroit (DTW)

United • Coach
Save 100% on your flight
per person
found 1 day ago
This hotel is tired, and the walls are very thin. Really needs a remodel. I wish I’d stayed at the Marriott around the corner.

Reviewed on Mar 24, 2025

Virgin Hotels Chicago
4.5-star property

Virgin Hotels Chicago

9.2/10 Wonderful! (1,320 reviews)

Jun 5 - Jun 7

2 night stay

Detroit (DTW) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Detroit (DTW)

United • Coach
Save 100% on your flight
per person
found 1 day ago
Absolutely loved this property. Super convenient, the metro and train stations a very short walk away. Right by the bean and river north. Cafe and commons club were fantastic, service was great by all staff.

Reviewed on Apr 6, 2025

Hilton Chicago/Magnificent Mile Suites
3.5-star property

Hilton Chicago/Magnificent Mile Suites

8.8/10 Excellent! (2,064 reviews)

Jun 5 - Jun 7

2 night stay

Detroit (DTW) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Detroit (DTW)

United • Coach
Save 100% on your flight
per person
found 1 day ago
We had a great stay and would definitely return! We liked the location—everything we needed was close by, and we felt completely safe traveling as a group of women with a child. The hotel was within walking distance to fabulous shopping and dining, which made our trip extra enjoyable. For anyone planning to explore beyond the immediate area, we highly recommend getting a bus or “L” pass. Public transportation was easy to navigate and made getting around the city a breeze. One of the highlights of our stay was the incredibly kind and welcoming bellman (we regret not getting his name!). He went out of his way to make us feel at home, and that warm hospitality really stood out. The only downside was the sleeper sofa—the mattress could definitely use an upgrade for better comfort. Overall, we had a great experience and would recommend this hotel to others.

Reviewed on Apr 24, 2025

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More About Flying To Chicago from Detroit

Route Information for Flights from Detroit to Chicago

Origin Airport IATA Code
DTT
Destination Airport IATA Code
CHI
Distance
234 mi
Direct Flight Airlines
JAL, Delta Air Lines, Air New Zealand, United Airlines, Qantas, SAS, Iberia, Korean Air, WestJet, Gulf Air, American Airlines, KLM, Qatar Airways, Air Canada, Austrian, Air France, Emirates, China Eastern Airlines, Copa Airlines, Aeromexico, Alaska Airlines, Cathay Pacific, Royal Jordanian, Finnair, ANA, Lufthansa, Virgin Atlantic, British Airways
Earliest Flight Arrival
9:58AM UTC
Latest Flight Arrival
12:45AM UTC

Flying from Detroit to Chicago

Detroit Metro Airport

The Orbitz.com website makes it easy to find cheap flights from Detroit to any destination. The Detroit Metro Airport is located at 9000 Middlebelt Road, approximately 21 miles from downtown Detroit. Twelve airlines service the airport, including Delta Airlines, Frontier, Air Tran and American Airlines. When you use Orbitz.com to book your flight, the website searches flights from all available airlines so you can choose a flight with cheap tickets.

Parking and Transportation

The Detroit Metro Airport offers long-term parking for $10 per day. It also runs complimentary shuttle services from the parking lots to the airport terminals. If you're traveling for more than four days, it's cheaper to take a cab to the airport. Cab fare from downtown Detroit costs $44.50. If you need access to a vehicle when you arrive at your destination, you can reserve a rental car using the Orbitz.com website. This way, you can get from the airport to your hotel without relying on public transportation.

Dining at the Airport

There are a variety of restaurants located at the airport including Chili's, Diego's Mexican Cantina, Detroit 500 and Fuddruckers. When you book your flight using Orbitz.com, you have plenty of time to grab a quick meal before your flight, because your travel arrangements are made before you arrive at the airport. The Orbitz.com website does more than find cheap flights from Detroit; it has all the tools you need to plan your entire trip.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Frequently asked questions

Are there non-stop flights from Detroit to Chicago?
There are 3 airlines that fly direct from Detroit, MI (DTW-Detroit Metropolitan Wayne County) to ORD, so get ready to click that “book” button. One of these popular carriers will have the flight you’re after:

  • United Airlines
  • Delta
  • American Airlines

What is the shortest flight from Detroit to Chicago?
It can take as little as 1 hour and 18 minutes to fly from Detroit Metropolitan Wayne County Airport (DTW) to O’Hare Airport. Take a seat and enjoy the service, because you’ll be coming in to land in no time.
What airlines fly from Detroit to Chicago most frequently?
Consider booking a ticket with Delta (DL), which frequently services this route. This airline operates 178 flights each month between Detroit Metropolitan Wayne County Airport (DTW) and ORD. United Airlines (UA) also travels from Detroit to Chicago. It’s another excellent choice and offers 178 flights each month.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.