$49 Cheap flight deals from Dallas (DFW) to Naperville (CHI)
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This Weekend's Flight Deals from Dallas to Naperville
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.
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$248 Roundtrip, found 3 hours ago
$248
Roundtrip
found 3 hours ago
DAL
Love Field
ORD
O'Hare Intl.
$251 Roundtrip, found 5 days ago
$251
Roundtrip
found 5 days ago
DAL
Love Field
ORD
O'Hare Intl.
$251 Roundtrip, found 5 days ago
$251
Roundtrip
found 5 days ago
DAL
Love Field
MDW
Midway Intl.
$364 Roundtrip, found 5 hours ago
$364
Roundtrip
found 5 hours ago
Airfares from $49 One Way, $105 Round Trip from Dallas to Naperville
Prices starting at $105 for return flights and $49 for one-way flights to Naperville were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
DFW
Dallas
MDW
Chicago
$105 Roundtrip, found 18 hours ago
$105
Roundtrip
found 18 hours ago
DFW
Dallas
RFD
Rockford
$190 Roundtrip, found 3 days ago
$190
Roundtrip
found 3 days ago
DFW
Dallas
ORD
Chicago
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
DAL
Dallas
MDW
Chicago
$192 Roundtrip, found 3 days ago
$192
Roundtrip
found 3 days ago
DAL
Dallas
ORD
Chicago
$211 Roundtrip, found 1 day ago
$211
Roundtrip
found 1 day ago
Naperville economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Ohio House Motel
8.8/10 Excellent! (1,126 reviews)
Aug 18 - Aug 23
5 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $853, price is now $618 per person
$618
per person
found 1 day ago
Reasonable price, clean room, helpful staff.
Reviewed on Jul 11, 2026
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (4,586 reviews)
Sep 5 - Sep 7
2 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $896, price is now $633 per person
$633
per person
found 1 day ago
Amazing location, great helpful staff, comfortable rooms. I will come back.
Reviewed on Jul 12, 2026
3.0-star property
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
8.6/10 Excellent! (2,518 reviews)
Aug 18 - Aug 23
5 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,133, price is now $813 per person
$813
per person
found 1 day ago
What a great place. Staff amazing and friendly. Gym was super. Location was perfect. Breakfast was an ok hotel buffet. But the room was awesome, huge and fully stocked. Staying here again.
Reviewed on Jul 11, 2026
Naperville business class flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Omni Chicago Hotel
9.2/10 Wonderful! (1,819 reviews)
Aug 14 - Aug 17
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • BusinessClass
Price was $1,176, price is now $892 per person
$892
per person
found 1 day ago
Staff was amazing, we had a single king bed corner suite with a separate room that has a pull out bed from the couch. It was a perfect setup for us because the kids had their own little room with their own tv and everything. The pullout couch bed was very uncomfortable, but we kinda figured it wouldn't be the best in the first place so that was alright. The king bed was pretty good, no complaints there... What we disliked was that the room was not properly cleaned before us. They didn't vacuum, there were beer caps and change on the floor. The toilet was for sure not cleaned after the last guests in the room because it was pretty bad. There were only two bath towels which wasn't a big deal cause they brought us more and they also brought us a microwave after asking, that was pretty nice. The really stupid thing with the king bed room was that the TV is literally all the way over to the left mounted on the wall where you couldn't see it very well while laying in bed... It is really really stupid if you see what im talking about here. Imagine laying in bed at a $300 a night hotel and you and your wife are trying to watch a TV thats WAY over on the left side of the room... Its actually comical how the set up is... Valet parking is insane at $90 a night so I would recommend finding parking elsewhere around the hotel if you can. Overall it was a OK stay, nothing incredible and definitely not worth the $300 plus $90 parking...
Reviewed on Jul 12, 2026
4.0-star property
Level Chicago – Old Town
9/10 Wonderful! (497 reviews)
Aug 14 - Aug 17
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $1,712, price is now $1,257 per person
$1,257
per person
found 1 day ago
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (4,586 reviews)
Aug 14 - Aug 17
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • BusinessClass
Price was $1,403, price is now $1,033 per person
$1,033
per person
found 1 day ago
Amazing location, great helpful staff, comfortable rooms. I will come back.
Reviewed on Jul 12, 2026
Naperville first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Omni Chicago Hotel
9.2/10 Wonderful! (1,819 reviews)
Sep 3 - Sep 8
5 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Dallas (DFW)
Delta • FirstClass
Price was $1,633, price is now $1,151 per person
$1,151
per person
found 18 hours ago
Staff was amazing, we had a single king bed corner suite with a separate room that has a pull out bed from the couch. It was a perfect setup for us because the kids had their own little room with their own tv and everything. The pullout couch bed was very uncomfortable, but we kinda figured it wouldn't be the best in the first place so that was alright. The king bed was pretty good, no complaints there... What we disliked was that the room was not properly cleaned before us. They didn't vacuum, there were beer caps and change on the floor. The toilet was for sure not cleaned after the last guests in the room because it was pretty bad. There were only two bath towels which wasn't a big deal cause they brought us more and they also brought us a microwave after asking, that was pretty nice. The really stupid thing with the king bed room was that the TV is literally all the way over to the left mounted on the wall where you couldn't see it very well while laying in bed... It is really really stupid if you see what im talking about here. Imagine laying in bed at a $300 a night hotel and you and your wife are trying to watch a TV thats WAY over on the left side of the room... Its actually comical how the set up is... Valet parking is insane at $90 a night so I would recommend finding parking elsewhere around the hotel if you can. Overall it was a OK stay, nothing incredible and definitely not worth the $300 plus $90 parking...
Reviewed on Jul 12, 2026
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (4,586 reviews)
Sep 3 - Sep 8
5 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Dallas (DFW)
Delta • FirstClass
Save 100% on your flight
Price was $2,023, price is now $1,284 per person
$1,284
per person
found 18 hours ago
Amazing location, great helpful staff, comfortable rooms. I will come back.
Reviewed on Jul 12, 2026
5.0-star property
Trump International Hotel & Tower Chicago
9.6/10 Exceptional! (1,910 reviews)
Sep 3 - Sep 8
5 night stay
Dallas (DFW) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Dallas (DFW)
Delta • FirstClass
Save 100% on your flight
Price was $2,551, price is now $1,824 per person
$1,824
per person
found 18 hours ago
I love Trump hotels the absolute BEST
Reviewed on Jul 10, 2026
More About Flying To Naperville from Dallas
Route Information for Flights from Dallas to Naperville
Origin Airport IATA Code | DFW |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Dallas to Naperville
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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.