$56 Cheap flight deals from Denver (DEN) to DeKalb (CHI)

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This Weekend's Flight Deals from Denver to DeKalb

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, Sep 6 - Wed, Sep 9
DEN
Denver Intl.
ORD
O'Hare Intl.
$253 Roundtrip, found 4 hours ago
$253
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Sep 6 from Denver Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $253 found 4 hours ago
Sat, Sep 5 - Sun, Sep 6
COS
Colorado Springs
ORD
O'Hare Intl.
$505 Roundtrip, found 1 day ago
$505
Roundtrip
found 1 day ago
Select United flight, departing Sat, Sep 5 from Colorado Springs to O'Hare Intl., returning Sun, Sep 6, priced at $505 found 1 day ago
Sun, Sep 6 - Wed, Sep 9
DEN
Denver Intl.
RFD
Greater Rockford
$558 Roundtrip, found 4 hours ago
$558
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sun, Sep 6 from Denver Intl. to Greater Rockford, returning Wed, Sep 9, priced at $558 found 4 hours ago
Fri, Sep 4 - Mon, Sep 7
COS
Colorado Springs
RFD
Greater Rockford
$887 Roundtrip, found 2 days ago
$887
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Sep 4 from Colorado Springs to Greater Rockford, returning Mon, Sep 7, priced at $887 found 2 days ago

Airfares from $56 One Way, $110 Round Trip from Denver to DeKalb

Prices starting at $110 for return flights and $56 for one-way flights to DeKalb were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Oct 22 - Wed, Oct 28
DEN
Denver
ORD
Chicago
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Denver to Chicago, returning Wed, Oct 28, priced at $110 found 1 day ago
Sat, Nov 14 - Mon, Nov 16
DEN
Denver
ORD
Chicago
$131 Roundtrip, found 5 days ago
$131
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Denver to Chicago, returning Mon, Nov 16, priced at $131 found 5 days ago
Mon, Sep 21 - Tue, Sep 22
DEN
Denver
RFD
Rockford
$212 Roundtrip, found 5 days ago
$212
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Sep 21 from Denver to Rockford, returning Tue, Sep 22, priced at $212 found 5 days ago
Tue, Sep 29 - Wed, Sep 30
DEN
Denver
ORD
Chicago
$229 Roundtrip, found 4 hours ago
$229
Roundtrip
found 4 hours ago
Select United flight, departing Tue, Sep 29 from Denver to Chicago, returning Wed, Sep 30, priced at $229 found 4 hours ago
Tue, Sep 29 - Wed, Sep 30
DEN
Denver
ORD
Chicago
$249 Roundtrip, found 4 hours ago
$249
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Sep 29 from Denver to Chicago, returning Wed, Sep 30, priced at $249 found 4 hours ago

DeKalb economy flight packages

Price found within the past 48 hours. Click for updated prices.
Renaissance Chicago Downtown Hotel
4.0-star property

Renaissance Chicago Downtown Hotel

9.2/10 Wonderful! (1,009 reviews)

Oct 29 - Nov 1

3 night stay

Denver (DEN) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Denver (DEN)

Frontier Airlines • Coach
Save 100% on your flight
Price was $950, price is now $600 per person
$600
per person
found 1 day ago
The hotel itself was nice, but communication and a few amenities were disappointing. I booked through Hotels.com and was told I would pay a $120 destination fee at the property. At check-in, I specifically asked what the destination package included and was told we received complimentary drinks, $15 bar vouchers, and other amenities. Later, after noticing an additional charge on my card, I was given different information about what was actually included. I was also told after the fact that Garrett Popcorn was included and that it was listed on a card given at check-in. No one explained this to us, so we never received it. If guests are paying a mandatory destination fee, staff should clearly explain what is included and how to redeem it. The rooftop bar was one of the main things we were excited about, but it doesn’t open until 4 p.m., so lunch wasn’t an option. It also filled up quickly, and hotel guests don’t receive priority seating. Lastly, most food options close around midnight, and there are no vending machines or convenient late-night options. There is a 7-Eleven within walking distance, but the area felt a little sketchy late at night. Overall, a nice hotel, but better communication and more consideration for hotel guests would improve the experience.

Reviewed on Aug 28, 2026

Four Seasons Hotel Chicago
5.0-star property

Four Seasons Hotel Chicago

9.4/10 Exceptional! (1,004 reviews)

Oct 14 - Oct 17

3 night stay

Denver (DEN) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,921, price is now $1,074 per person
$1,074
per person
found 1 day ago
The staff was so kind and helpful. Great location and dining options. The room was spotless and comfortable

Reviewed on Aug 30, 2026

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,577 reviews)

Oct 23 - Oct 27

4 night stay

Denver (DEN) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,206, price is now $770 per person
$770
per person
found 1 day ago

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More About Flying To DeKalb from Denver

Route Information for Flights from Denver to DeKalb

Origin Airport IATA Code
DEN
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Denver to DeKalb

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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.